Bioorganic chemistry among medical students. Bioorganic chemistry Hemoglobin and its derivatives

Plan 1. Subject and significance of bioorganic chemistry 2. Classification and nomenclature of organic compounds 3. Methods of depicting organic molecules 4. Chemical bonding in bioorganic molecules 5. Electronic effects. Mutual influence of atoms in a molecule 6. Classification of chemical reactions and reagents 7. Concept of the mechanisms of chemical reactions 2

Subject of bioorganic chemistry 3 Bioorganic chemistry is an independent branch of chemical science that studies the structure, properties and biological functions of chemical compounds of organic origin that take part in the metabolism of living organisms.

The objects of study of bioorganic chemistry are low-molecular biomolecules and biopolymers (proteins, nucleic acids and polysaccharides), bioregulators (enzymes, hormones, vitamins and others), natural and synthetic physiologically active compounds, including drugs and substances with toxic effects. Biomolecules are bioorganic compounds that are part of living organisms and specialized for the formation of cellular structures and participation in biochemical reactions, form the basis of metabolism (metabolism) and the physiological functions of living cells and multicellular organisms in general. 4 Classification of bioorganic compounds

Metabolism is a set of chemical reactions that occur in the body (in vivo). Metabolism is also called metabolism. Metabolism can occur in two directions - anabolism and catabolism. Anabolism is the synthesis in the body of complex substances from relatively simple ones. It occurs with the expenditure of energy (endothermic process). Catabolism, on the contrary, is the breakdown of complex organic compounds into simpler ones. It occurs with the release of energy (exothermic process). Metabolic processes take place with the participation of enzymes. Enzymes play the role of biocatalysts in the body. Without enzymes, biochemical processes would either not occur at all, or would proceed very slowly, and the body would not be able to maintain life. 5

Bioelements. The composition of bioorganic compounds, in addition to carbon atoms (C), which form the basis of any organic molecule, also includes hydrogen (H), oxygen (O), nitrogen (N), phosphorus (P) and sulfur (S). These bioelements (organogens) are concentrated in living organisms in quantities that are over 200 times higher than their content in inanimate objects. The noted elements make up over 99% of the elemental composition of biomolecules. 6

Bioorganic chemistry arose from the depths of organic chemistry and is based on its ideas and methods. In the history of development, organic chemistry has the following stages: empirical, analytical, structural and modern. The period from man's first acquaintance with organic substances to the end of the 18th century is considered empirical. The main result of this period was that people realized the importance of elemental analysis and the establishment of atomic and molecular masses. The theory of vitalism - life force (Berzelius). The analytical period continued until the 60s of the 19th century. It was marked by the fact that from the end of the first quarter of the 19th century a number of promising discoveries were made that dealt a crushing blow to the vitalistic theory. The first in this series was Berzelius's student, the German chemist Wöhler. He made a number of discoveries in 1824 - the synthesis of oxalic acid from cyanogen: (CN) 2 HOOC - COOH r. – synthesis of urea from ammonium cyanate: NH 4 CNO NH 2 – C – NH 2 O 8

In 1853, C. Gerard developed the “theory of types” and used it to classify organic compounds. According to Gerard, more complex organic compounds can be produced from the following four main types of substances: HHHH type HHHH O type WATER H Cl type HYDROGEN CHLORIDE HHHHN N type AMMONIA Since 1857, at the suggestion of F. A. Kekule, hydrocarbons began to be classified as methane type HHHNNHH C 9

Basic provisions of the theory of the structure of organic compounds (1861) 1) atoms in molecules are connected to each other by chemical bonds in accordance with their valency; 2) atoms in molecules of organic substances are connected to each other in a certain sequence, which determines the chemical structure (structure) of the molecule; 3) the properties of organic compounds depend not only on the number and nature of their constituent atoms, but also on the chemical structure of the molecules; 4) in organic molecules there is interaction between atoms, both bound to each other and unbound; 5) the chemical structure of a substance can be determined by studying its chemical transformations and, conversely, its properties can be characterized by the structure of a substance. 10

Basic provisions of the theory of the structure of organic compounds (1861) A structural formula is an image of the sequence of bonds of atoms in a molecule. Gross formula - CH 4 O or CH 3 OH Structural formula Simplified structural formulas are sometimes called rational Molecular formula - the formula of an organic compound, which indicates the number of atoms of each element in the molecule. For example: C 5 H 12 - pentane, C 6 H 6 - gasoline, etc. 11

Stages of development of bioorganic chemistry As a separate field of knowledge that combines the conceptual principles and methodology of organic chemistry on the one hand and molecular biochemistry and molecular pharmacology on the other hand, bioorganic chemistry was formed in the twentieth century based on developments in the chemistry of natural substances and biopolymers. Modern bioorganic chemistry has acquired fundamental significance thanks to the work of W. Stein, S. Moore, F. Sanger (analysis of amino acid composition and determination of the primary structure of peptides and proteins), L. Pauling and H. Astbury (clarification of the structure of the -helix and -structure and their significance in the implementation of the biological functions of protein molecules), E. Chargaff (deciphering the features of the nucleotide composition of nucleic acids), J. Watson, Fr. Crick, M. Wilkins, R. Franklin (establishing the patterns of the spatial structure of the DNA molecule), G. Corani (chemical gene synthesis), etc. 14

Classification of organic compounds according to the structure of the carbon skeleton and the nature of the functional group The huge number of organic compounds prompted chemists to classify them. The classification of organic compounds is based on two classification criteria: 1. The structure of the carbon skeleton 2. The nature of the functional groups Classification according to the method of structure of the carbon skeleton: 1. Acyclic (alkanes, alkenes, alkynes, alkadienes); 2. Cyclic 2.1. Carbocyclic (alicyclic and aromatic) 2.2. Heterocyclic 15 Acyclic compounds are also called aliphatic. These include substances with an open carbon chain. Acyclic compounds are divided into saturated (or saturated) C n H 2n+2 (alkanes, paraffins) and unsaturated (unsaturated). The latter include alkenes C n H 2n, alkynes C n H 2n -2, alkadienes C n H 2n -2.

16 Cyclic compounds contain rings (cycles) within their molecules. If the cycles contain only carbon atoms, then such compounds are called carbocyclic. In turn, carbocyclic compounds are divided into alicyclic and aromatic. Alicyclic hydrocarbons (cycloalkanes) include cyclopropane and its homologues - cyclobutane, cyclopentane, cyclohexane, and so on. If the cyclic system, in addition to the hydrocarbon, also includes other elements, then such compounds are classified as heterocyclic.

Classification by the nature of a functional group A functional group is an atom or a group of atoms connected in a certain way, the presence of which in a molecule of an organic substance determines the characteristic properties and its belonging to one or another class of compounds. Based on the number and homogeneity of functional groups, organic compounds are divided into mono-, poly- and heterofunctional. Substances with one functional group are called monofunctional; substances with several identical functional groups are called polyfunctional. Compounds containing several different functional groups are heterofunctional. It is important that compounds of the same class are combined into homologous series. A homologous series is a series of organic compounds with the same functional groups and the same structure; each representative of the homologous series differs from the previous one by a constant unit (CH 2), which is called the homologous difference. Members of a homologous series are called homologues. 17

Nomenclature systems in organic chemistry - trivial, rational and international (IUPAC) Chemical nomenclature is a set of names of individual chemical substances, their groups and classes, as well as rules for compiling their names. Chemical nomenclature is a set of names of individual chemical substances, their groups and classes, as well as rules compiling their names. The trivial (historical) nomenclature is associated with the process of obtaining substances (pyrogallol - a product of pyrolysis of gallic acid), the source of origin from which it was obtained (formic acid), etc. Trivial names of compounds are widely used in the chemistry of natural and heterocyclic compounds (citral, geraniol, thiophene, pyrrole, quinoline, etc.). Trivial (historical) nomenclature is associated with the process of obtaining substances (pyrogallol is a product of pyrolysis of gallic acid), the source of origin, from which was obtained (formic acid), etc. Trivial names of compounds are widely used in the chemistry of natural and heterocyclic compounds (citral, geraniol, thiophene, pyrrole, quinoline, etc.). Rational nomenclature is based on the principle of dividing organic compounds into homologous series. All substances in a certain homologous series are considered as derivatives of the simplest representative of this series - the first or sometimes the second. In particular, for alkanes - methane, for alkenes - ethylene, etc. The rational nomenclature is based on the principle of dividing organic compounds into homologous series. All substances in a certain homologous series are considered as derivatives of the simplest representative of this series - the first or sometimes the second. In particular, for alkanes - methane, for alkenes - ethylene, etc. 18

International nomenclature (IUPAC). The rules of modern nomenclature were developed in 1957 at the 19th Congress of the International Union of Pure and Applied Chemistry (IUPAC). Radical functional nomenclature. These names are based on the name of the functional class (alcohol, ether, ketone, etc.), which is preceded by the names of hydrocarbon radicals, for example: allyl chloride, diethyl ether, dimethyl ketone, propyl alcohol, etc. Substitute nomenclature. Nomenclature rules. The parent structure is the structural fragment of the molecule (molecular skeleton) underlying the name of the compound, the main carbon chain of atoms for alicyclic compounds, and the cycle for carbocyclic compounds. 19

Chemical bond in organic molecules Chemical bond is the phenomenon of interaction between the outer electron shells (valence electrons of atoms) and atomic nuclei, which determines the existence of a molecule or crystal as a whole. As a rule, an atom, accepting or donating an electron or forming a common electron pair, tends to acquire a configuration of the outer electron shell similar to that of noble gases. The following types of chemical bonds are characteristic of organic compounds: - ionic bond - covalent bond - donor - acceptor bond - hydrogen bond. There are also some other types of chemical bonds (metallic, one-electron, two-electron, three-center), but they are practically not found in organic compounds. 20

Types of bonds in organic compounds The most characteristic of organic compounds is a covalent bond. A covalent bond is the interaction of atoms, which is realized through the formation of a common electron pair. This type of bond is formed between atoms that have comparable electronegativity values. Electronegativity is a property of an atom that shows the ability to attract electrons to itself from other atoms. A covalent bond can be polar or non-polar. A non-polar covalent bond occurs between atoms with the same electronegativity value

Types of bonds in organic compounds A polar covalent bond is formed between atoms that have different electronegativity values. In this case, the bonded atoms acquire partial charges δ+δ+ δ-δ- A special subtype of covalent bond is the donor-acceptor bond. As in previous examples, this type of interaction is due to the presence of a common electron pair, but the latter is provided by one of the atoms forming the bond (donor) and accepted by another atom (acceptor) 24

Types of bonds in organic compounds An ionic bond is formed between atoms that differ greatly in electronegativity values. In this case, the electron of the less electronegative element (often a metal) is completely transferred to the more electronegative element. This electron transition causes the appearance of a positive charge on the less electronegative atom and a negative charge on the more electronegative one. Thus, two ions with opposite charges are formed, between which there is an electrovalent interaction. 25

Types of Bonds in Organic Compounds A hydrogen bond is an electrostatic interaction between a hydrogen atom, which is bonded in a highly polar manner, and electron pairs of oxygen, fluorine, nitrogen, sulfur and chlorine. This type of interaction is a rather weak interaction. Hydrogen bonding can be intermolecular or intramolecular. Intermolecular hydrogen bond (interaction between two molecules of ethyl alcohol) Intramolecular hydrogen bond in salicylic aldehyde 26

Chemical bonding in organic molecules The modern theory of chemical bonding is based on the quantum mechanical model of a molecule as a system consisting of electrons and atomic nuclei. The cornerstone concept of quantum mechanical theory is the atomic orbital. An atomic orbital is a part of space in which the probability of finding electrons is maximum. Bonding can thus be viewed as the interaction (“overlap”) of orbitals that each carry one electron with opposite spins. 27

Hybridization of atomic orbitals According to quantum mechanical theory, the number of covalent bonds formed by an atom is determined by the number of one-electron atomic orbitals (the number of unpaired electrons). The carbon atom in its ground state has only two unpaired electrons, but the possible transition of an electron from 2s to 2 pz makes it possible to form four covalent bonds. The state of a carbon atom in which it has four unpaired electrons is called “excited.” Despite the fact that carbon orbitals are unequal, it is known that the formation of four equivalent bonds is possible due to the hybridization of atomic orbitals. Hybridization is a phenomenon in which the same number of orbitals of the same shape and number are formed from several orbitals of different shapes and similar in energy. 28

Hybrid states of the carbon atom in organic molecules FIRST HYBRID STATE The C atom is in a state of sp 3 hybridization, forms four σ bonds, forms four hybrid orbitals, which are arranged in the shape of a tetrahedron (bond angle) σ bond 31

Hybrid states of the carbon atom in organic molecules SECOND HYBRID STATE The C atom is in a state of sp 2 hybridization, forms three σ-bonds, forms three hybrid orbitals, which are arranged in the shape of a flat triangle (bond angle 120) σ-bonds π-bond 32

Hybrid states of the carbon atom in organic molecules THIRD HYBRID STATE The C atom is in a state of sp-hybridization, forms two σ-bonds, forms two hybrid orbitals, which are arranged in a line (bond angle 180) σ-bonds π-bonds 33

Characteristics of chemical bonds POLING scale: F-4.0; O – 3.5; Cl – 3.0; N – 3.0; Br – 2.8; S – 2.5; C-2.5; H-2.1. difference 1.7

Characteristics of chemical bonds Bond polarizability is a shift in electron density under the influence of external factors. Bond polarizability is the degree of electron mobility. As the atomic radius increases, the polarizability of electrons increases. Therefore, the polarizability of the Carbon - halogen bond increases as follows: C-F

Electronic effects. Mutual influence of atoms in a molecule 39 According to modern theoretical concepts, the reactivity of organic molecules is predetermined by the displacement and mobility of electron clouds that form a covalent bond. In organic chemistry, two types of electron displacements are distinguished: a) electronic displacements occurring in the -bond system, b) electronic displacements transmitted by the -bond system. In the first case, the so-called inductive effect takes place, in the second - a mesomeric effect. The inductive effect is a redistribution of electron density (polarization) resulting from the difference in electronegativity between the atoms of a molecule in a system of bonds. Due to the insignificant polarizability of the -bonds, the inductive effect quickly fades away and after 3-4 bonds it almost does not appear.

Electronic effects. Mutual influence of atoms in a molecule 40 The concept of the inductive effect was introduced by K. Ingold, and he also introduced the following designations: –I-effect in the case of a decrease in electron density by a substituent +I-effect in the case of an increase in electron density by a substituent A positive inductive effect is exhibited by alkyl radicals (CH 3, C 2 H 5 - etc.). All other substituents bonded to the carbon atom exhibit a negative inductive effect.

Electronic effects. Mutual influence of atoms in a molecule 41 The mesomeric effect is the redistribution of electron density along a conjugated system. Conjugated systems include molecules of organic compounds in which double and single bonds alternate or when an atom with a lone pair of electrons in the p-orbital is located next to the double bond. In the first case, - conjugation takes place, and in the second case, p, -conjugation takes place. Coupled systems come in open and closed circuit configurations. Examples of such compounds are 1,3-butadiene and gasoline. In the molecules of these compounds, carbon atoms are in a state of sp 2 hybridization and, due to non-hybrid p-orbitals, form -bonds that mutually overlap and form a single electron cloud, that is, conjugation takes place.

Electronic effects. Mutual influence of atoms in a molecule 42 There are two types of mesomeric effect - positive mesomeric effect (+M) and negative mesomeric effect (-M). A positive mesomeric effect is exhibited by substituents that provide p-electrons to the conjugated system. These include: -O, -S -NH 2, -OH, -OR, Hal (halogens) and other substituents that have a negative charge or a lone pair of electrons. The negative mesomeric effect is characteristic of substituents that absorb electron density from the conjugated system. These include substituents that have multiple bonds between atoms with different electronegativity: - N0 2 ; -SO 3 H; >C=O; -COON and others. The mesomeric effect is graphically reflected by a bent arrow, which shows the direction of electron displacement. Unlike the induction effect, the mesomeric effect does not go out. It is transmitted completely throughout the system, regardless of the length of the interfacing chain. C=O; -COON and others. The mesomeric effect is graphically reflected by a bent arrow, which shows the direction of electron displacement. Unlike the induction effect, the mesomeric effect does not go out. It is transmitted completely throughout the system, regardless of the length of the interfacing chain.">

Types of chemical reactions 43 A chemical reaction can be considered as the interaction of a reagent and substrate. Depending on the method of breaking and forming a chemical bond in molecules, organic reactions are divided into: a) homolytic b) heterolytic c) molecular Homolytic or free radical reactions are caused by homolytic cleavage of the bond, when each atom has one electron left, that is, radicals are formed . Homolytic cleavage occurs at high temperatures, the action of a light quantum, or catalysis.

Heterolytic or ionic reactions proceed in such a way that a pair of bonding electrons remains near one of the atoms and ions are formed. A particle with an electron pair is called nucleophilic and has a negative charge (-). A particle without an electron pair is called electrophilic and has a positive charge (+). 44 Types of chemical reactions

Mechanism of a chemical reaction 45 The mechanism of a reaction is the set of elementary (simple) stages that make up a given reaction. The reaction mechanism most often includes the following stages: activation of the reagent with the formation of an electrophile, nucleophile or free radical. To activate a reagent, a catalyst is usually needed. In the second stage, the activated reagent interacts with the substrate. In this case, intermediate particles (intermediates) are formed. The latter include -complexes, -complexes (carbocations), carbanions, and new free radicals. At the final stage, the addition or elimination of a particle to (from) the intermediate formed in the second stage takes place with the formation of the final reaction product. If a reagent generates a nucleophile upon activation, then these are nucleophilic reactions. They are marked with the letter N - (in the index). In the case where the reagent generates an electrophile, the reactions are classified as electrophilic (E). The same can be said about free radical reactions (R).

Nucleophiles are reagents that have a negative charge or an atom enriched in electron density: 1) anions: OH -, CN -, RO -, RS -, Hal - and other anions; 2) neutral molecules with lone pairs of electrons: NH 3, NH 2 R, H 2 O, ROH and others; 3) molecules with excess electron density (having - bonds). Electrophiles are reagents that have a positive charge or an atom depleted in electron density: 1) cations: H + (proton), HSO 3 + (hydrogen sulfonium ion), NO 2 + (nitronium ion), NO (nitrosonium ion) and other cations; 2) neutral molecules with a vacant orbital: AlCl 3, FeBr 3, SnCl 4, BF 4 (Lewis acids), SO 3; 3) molecules with depleted electron density on the atom. 46

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Modern bioorganic chemistry is a branched field of knowledge, the foundation of many biomedical disciplines and, first of all, biochemistry, molecular biology, genomics, proteomics and

bioinformatics, immunology, pharmacology.

The program is based on a systematic approach to building the entire course on a single theoretical basis.

basis based on ideas about the electronic and spatial structure of organic

compounds and mechanisms of their chemical transformations. The material is presented in the form of 5 sections, the most important of which are: “Theoretical foundations of the structure of organic compounds and factors determining their reactivity”, “Biologically important classes of organic compounds” and “Biopolymers and their structural components. Lipids"

The program is aimed at specialized teaching of bioorganic chemistry at a medical university, and therefore the discipline is called “bioorganic chemistry in medicine.” The profiling of teaching bioorganic chemistry is served by consideration of the historical relationship between the development of medicine and chemistry, including organic, increased attention to classes of biologically important organic compounds (heterofunctional compounds, heterocycles, carbohydrates, amino acids and proteins, nucleic acids, lipids) as well as biologically important reactions of these classes of compounds ). A separate section of the program is devoted to consideration of the pharmacological properties of certain classes of organic compounds and the chemical nature of certain classes of drugs.

Considering the important role of “oxidative stress diseases” in the structure of modern human morbidity, the program pays special attention to free radical oxidation reactions, detection of end products of free radical lipid oxidation in laboratory diagnostics, natural antioxidants and antioxidant drugs. The program provides consideration of environmental problems, namely the nature of xenobiotics and the mechanisms of their toxic effect on living organisms.

1. The purpose and objectives of training.

1.1. The purpose of teaching the subject bioorganic chemistry in medicine: to develop an understanding of the role of bioorganic chemistry as the foundation of modern biology, a theoretical basis for explaining the biological effects of bioorganic compounds, the mechanisms of action of drugs and the creation of new drugs. To develop knowledge of the relationship between the structure, chemical properties and biological activity of the most important classes of bioorganic compounds, to teach how to apply the acquired knowledge when studying subsequent disciplines and in professional activities.

1.2. Objectives of teaching bioorganic chemistry:

1. Formation of knowledge of the structure, properties and reaction mechanisms of the most important classes of bioorganic compounds, which determine their medical and biological significance.

2. Formation of ideas about the electronic and spatial structure of organic compounds as a basis for explaining their chemical properties and biological activity.

3. Formation of skills and practical skills:

classify bioorganic compounds according to the structure of the carbon skeleton and functional groups;

use the rules of chemical nomenclature to indicate the names of metabolites, drugs, xenobiotics;

identify reaction centers in molecules;

be able to carry out qualitative reactions that have clinical and laboratory significance.

2. The place of discipline in the structure of OOP:

The discipline "Bioorganic chemistry" is an integral part of the discipline "Chemistry", which belongs to the mathematical, natural science cycle of disciplines.

The basic knowledge necessary to study the discipline is formed in the cycle of mathematical, natural science disciplines: physics, mathematics; medical informatics; chemistry; biology; anatomy, histology, embryology, cytology; normal physiology; microbiology, virology.

It is a prerequisite for studying the disciplines:

biochemistry;

pharmacology;

microbiology, virology;

immunology;

professional disciplines.

Disciplines studied in parallel, providing interdisciplinary connections within the framework of the basic part of the curriculum:

chemistry, physics, biology, 3. List of disciplines and topics that students need to master to study bioorganic chemistry.

General chemistry. The structure of the atom, the nature of a chemical bond, types of bonds, classes of chemical substances, types of reactions, catalysis, reaction of the medium in aqueous solutions.

Organic chemistry. Classes of organic substances, nomenclature of organic compounds, configuration of the carbon atom, polarization of atomic orbitals, sigma and pi bonds. Genetic relationship of classes of organic compounds. Reactivity of different classes of organic compounds.

Physics. The structure of the atom. Optics - ultraviolet, visible and infrared regions of the spectrum.

Interaction of light with matter - transmission, absorption, reflection, scattering. Polarized light.

Biology. Genetic code. Chemical basis of heredity and variability.

Latin. Mastering terminology.

Foreign language. Ability to work with foreign literature.

4. Sections of the discipline and interdisciplinary connections with the provided (subsequent) disciplines No. sections of this discipline necessary for studying the provided No. Name of the provided sub-disciplines (subsequent) disciplines (subsequent) disciplines 1 2 3 4 5 1 Chemistry + + + + + Biology + - - + + Biochemistry + + + + + + 4 Microbiology, virology + + - + + + 5 Immunology + - - - + Pharmacology + + - + + + 7 Hygiene + - + + + Professional disciplines + - - + + + 5. Requirements for the level of mastery of the discipline content Achieving the learning goal The discipline “Bioorganic Chemistry” involves the implementation of a number of targeted problem tasks, as a result of which students must develop certain competencies, knowledge, skills, and must acquire certain practical skills.

5.1. The student must have:

5.1.1. General cultural competencies:

the ability and willingness to analyze socially significant problems and processes, to use in practice the methods of the humanities, natural sciences, biomedical and clinical sciences in various types of professional and social activities (OK-1);

5.1.2. Professional competencies (PC):

ability and willingness to apply basic methods, methods and means of obtaining, storing, processing scientific and professional information; receive information from various sources, including the use of modern computer tools, network technologies, databases and the ability and willingness to work with scientific literature, analyze information, conduct searches, turn what you read into a means for solving professional problems (highlight the main provisions, consequences from them and suggestions);

ability and readiness to participate in setting scientific problems and their experimental implementation (PC-2, PC-3, PC-5, PC-7).

5.2. The student must know:

Principles of classification, nomenclature and isomerism of organic compounds.

Fundamentals of theoretical organic chemistry, which are the basis for studying the structure and reactivity of organic compounds.

The spatial and electronic structure of organic molecules and the chemical transformations of substances that are participants in life processes, in direct connection with their biological structure, chemical properties and biological role of the main classes of biologically important organic compounds.

5.3. The student must be able to:

Classify organic compounds according to the structure of the carbon skeleton and the nature of functional groups.

Compose formulas by name and name typical representatives of biologically important substances and drugs by structural formula.

Identify functional groups, acidic and basic centers, conjugated and aromatic fragments in molecules to determine the chemical behavior of organic compounds.

Predict the direction and result of chemical transformations of organic compounds.

5.4. The student must have:

Skills of independent work with educational, scientific and reference literature; conduct a search and draw general conclusions.

Have skills in handling chemical glassware.

Have the skills to work safely in a chemical laboratory and the ability to handle caustic, poisonous, highly volatile organic compounds, work with burners, alcohol lamps and electric heating devices.

5.5. Forms of knowledge control 5.5.1. Current control:

Diagnostic control of material assimilation. It is carried out periodically mainly to control knowledge of formula material.

Educational computer control in every lesson.

Test tasks requiring the ability to analyze and generalize (see Appendix).

Scheduled colloquiums upon completion of the study of large sections of the program (see Appendix).

5.5.2 Final control:

Test (carried out in two stages):

C.2 - Mathematical, natural science and medical-biological General labor intensity:

2 Classification, nomenclature and Classification and classification characteristics of organic modern physical compounds: the structure of the carbon skeleton and the nature of the functional group.

chemical methods Functional groups, organic radicals. Biologically important studies of bioorganic classes of organic compounds: alcohols, phenols, thiols, ethers, sulfides, aldehyde compounds, ketones, carboxylic acids and their derivatives, sulfonic acids.

IUPAC nomenclature. Varieties of international nomenclature: substitutive and radical-functional nomenclature. The value of knowledge 3 Theoretical foundations of the structure of organic compounds and the Theory of the structure of organic compounds by A.M. Butlerov. The main factors determining their positions. Structural formulas. The nature of the carbon atom by position and reactivity. chains. Isomerism as a specific phenomenon of organic chemistry. Types of Stereoisomerism.

Chirality of molecules of organic compounds as a cause of optical isomerism. Stereoisomerism of molecules with one center of chirality (enantiomerism). Optical activity. Glyceraldehyde as a configuration standard. Fischer projection formulas. D and L System of Stereochemical Nomenclature. Ideas about R,S-nomenclature.

Stereoisomerism of molecules with two or more chirality centers: enantiomerism and diastereomerism.

Stereoisomerism in a series of compounds with a double bond (Pydiastereomerism). Cis and trans isomers. Stereoisomerism and biological activity of organic compounds.

Mutual influence of atoms: causes of occurrence, types and methods of its transmission in molecules of organic compounds.

Pairing. Pairing in open circuits (Pi-Pi). Conjugated bonds. Diene structures in biologically important compounds: 1,3-dienes (butadiene), polyenes, alpha, beta-unsaturated carbonyl compounds, carboxyl group. Coupling as a system stabilization factor. Conjugation energy. Conjugation in arenes (Pi-Pi) and heterocycles (p-Pi).

Aromaticity. Aromaticity criteria. Aromaticity of benzenoid (benzene, naphthalene, anthracene, phenanthrene) and heterocyclic (furan, thiophene, pyrrole, imidazole, pyridine, pyrimidine, purine) compounds. Widespread occurrence of conjugated structures in biologically important molecules (porphin, heme, etc.).

Bond polarization and electronic effects (inductive and mesomeric) as the cause of the uneven distribution of electron density in the molecule. Substituents are electron donors and electron acceptors.

The most important substituents and their electronic effects. Electronic effects of substituents and reactivity of molecules. Orientation rule in the benzene ring, substituents of the first and second kind.

Acidity and basicity of organic compounds.

Acidity and basicity of neutral molecules of organic compounds with hydrogen-containing functional groups (amines, alcohols, thiols, phenols, carboxylic acids). Acids and bases according to Bronsted-Lowry and Lewis. Conjugate pairs of acids and bases. Anion acidity and stability. Quantitative assessment of the acidity of organic compounds based on Ka and pKa values.

Acidity of various classes of organic compounds. Factors that determine the acidity of organic compounds: electronegativity of the nonmetal atom (C-H, N-H, and O-H acids); polarizability of a nonmetal atom (alcohols and thiols, thiol poisons); nature of the radical (alcohols, phenols, carboxylic acids).

Basicity of organic compounds. n-bases (heterocycles) and pi-bases (alkenes, alkanedienes, arenes). Factors that determine the basicity of organic compounds: electronegativity of the heteroatom (O- and N bases); polarizability of a nonmetal atom (O- and S-base); nature of the radical (aliphatic and aromatic amines).

The importance of the acid-base properties of neutral organic molecules for their reactivity and biological activity.

Hydrogen bonding as a specific manifestation of acid-base properties. General patterns of reactivity of organic compounds as the chemical basis of their biological functioning.

Reaction mechanisms of organic compounds.

Classification of reactions of organic compounds according to the result of substitution, addition, elimination, rearrangement, redox and according to the mechanism - radical, ionic (electrophilic, nucleophilic). Types of covalent bond cleavage in organic compounds and the resulting particles: homolytic cleavage (free radicals) and heterolytic cleavage (carbocations and carbonanions).

Electronic and spatial structure of these particles and factors determining their relative stability.

Homolytic radical substitution reactions in alkanes involving C-H bonds of the sp 3-hybridized carbon atom. Free radical oxidation reactions in a living cell. Reactive (radical) forms of oxygen. Antioxidants. Biological significance.

Electrophilic addition reactions (Ae): heterolytic reactions involving the Pi bond. Mechanism of ethylene halogenation and hydration reactions. Acid catalysis. Influence of static and dynamic factors on the regioselectivity of reactions. Peculiarities of reactions of addition of hydrogen-containing substances to the Pi bond in unsymmetrical alkenes. Markovnikov's rule. Features of electrophilic addition to conjugated systems.

Electrophilic substitution reactions (Se): heterolytic reactions involving an aromatic system. Mechanism of electrophilic substitution reactions in arenes. Sigma complexes. Reactions of alkylation, acylation, nitration, sulfonation, halogenation of arenes. Orientation rule.

Substitutes of the 1st and 2nd kind. Features of electrophilic substitution reactions in heterocycles. Orienting influence of heteroatoms.

Reactions of nucleophilic substitution (Sn) at sp3-hybridized carbon atom: heterolytic reactions caused by polarization of the carbon-heteroatom sigma bond (halogen derivatives, alcohols). The influence of electronic and spatial factors on the reactivity of compounds in nucleophilic substitution reactions.

Hydrolysis reaction of halogen derivatives. Alkylation reactions of alcohols, phenols, thiols, sulfides, ammonia and amines. The role of acid catalysis in nucleophilic substitution of the hydroxyl group.

Deamination of compounds with a primary amino group. Biological role of alkylation reactions.

Elimination reactions (dehydrohalogenation, dehydration).

Increased CH acidity as a cause of elimination reactions accompanying nucleophilic substitution at the sp3-hybridized carbon atom.

Nucleophilic addition reactions (An): heterolytic reactions involving the pi carbon-oxygen bond (aldehydes, ketones). Classes of carbonyl compounds. Representatives. Preparation of aldehydes, ketones, carboxylic acids. Structure and reactivity of the carbonyl group. Influence of electronic and spatial factors. Mechanism of An reactions: role of protonation in increasing carbonyl reactivity. Biologically important reactions of aldehydes and ketones: hydrogenation, oxidation-reduction of aldehydes (dismutation reaction), oxidation of aldehydes, formation of cyanohydrins, hydration, formation of hemiacetals, imines. Aldol addition reactions. Biological significance.

Nucleophilic substitution reactions at the sp2-hybridized carbon atom (carboxylic acids and their functional derivatives).

The mechanism of nucleophilic substitution reactions (Sn) at the sp2 hybridized carbon atom. Acylation reactions - the formation of anhydrides, esters, thioesters, amides - and their reverse hydrolysis reactions. Biological role of acylation reactions. Acidic properties of carboxylic acids according to the O-H group.

Oxidation and reduction reactions of organic compounds.

Redox reactions, electronic mechanism.

Oxidation states of carbon atoms in organic compounds. Oxidation of primary, secondary and tertiary carbon atoms. Oxidability of various classes of organic compounds. Ways of oxygen utilization in the cell.

Energetic oxidation. Oxidase reactions. Oxidation of organic substances is the main source of energy for chemotrophs. Plastic oxidation.

4 Biologically important classes of organic compounds Polyhydric alcohols: ethylene glycol, glycerol, inositol. Education Hydroxy acids: classification, nomenclature, representatives of lactic, betahydroxybutyric, gammahydroxybutyric, malic, tartaric, citric, reductive amination, transamination and decarboxylation.

Amino acids: classification, representatives of beta and gamma isomers: aminopropane, gamma-aminobutyric, epsilonaminocaproic. Reaction Salicylic acid and its derivatives (acetylsalicylic acid is an antipyretic, anti-inflammatory and anti-rheumatic agent, enteroseptol and 5-NOK. The isoquinoline core as the basis of opium alkaloids, antispasmodics (papaverine) and analgesics (morphine). Acridine derivatives are disinfectants.

xanthine derivatives - caffeine, theobromine and theophylline, indole derivatives reserpine, strychnine, pilocarpine, quinoline derivatives - quinine, isoquinoline morphine and papaverine.

cephalosproins are derivatives of cephalosporanic acid, tetracyclines are derivatives of naphthacene, streptomycins are amyloglycosides. Semi-synthetic 5 Biopolymers and their structural components. Lipids. Definition. Classification. Functions.

Cyclo-oxotautomerism. Mutarotation. Derivatives of monosaccharides deoxysugar (deoxyribose) and amino sugar (glucosamine, galactosamine).

Oligosaccharides. Disaccharides: maltose, lactose, sucrose. Structure. Oglycosidic bond. Restorative properties. Hydrolysis. Biological (pathway of amino acid breakdown); radical reactions - hydroxylation (formation of oxy-derivatives of amino acids). Peptide bond formation.

Peptides. Definition. Structure of the peptide group. Functions.

Biologically active peptides: glutathione, oxytocin, vasopressin, glucagon, neuropeptides, kinin peptides, immunoactive peptides (thymosin), inflammatory peptides (difexin). The concept of cytokines. Antibiotic peptides (gramicidin, actinomycin D, cyclosporine A). Peptide toxins. Relationship between the biological effects of peptides and certain amino acid residues.

Squirrels. Definition. Functions. Levels of protein structure. The primary structure is the sequence of amino acids. Research methods. Partial and complete hydrolysis of proteins. The importance of determining the primary structure of proteins.

Directed site-specific mutagenesis as a method for studying the relationship between the functional activity of proteins and the primary structure. Congenital disorders of the primary structure of proteins - point mutations. Secondary structure and its types (alpha helix, beta structure). Tertiary structure.

Denaturation. The concept of active centers. Quaternary structure of oligomeric proteins. Cooperative properties. Simple and complex proteins: glycoproteins, lipoproteins, nucleoproteins, phosphoproteins, metalloproteins, chromoproteins.

Nitrogen bases, nucleosides, nucleotides and nucleic acids.

Definition of the concepts nitrogenous base, nucleoside, nucleotide and nucleic acid. Purine (adenine and guanine) and pyrimidine (uracil, thymine, cytosine) nitrogenous bases. Aromatic properties. Resistance to oxidative degradation as a basis for fulfilling a biological role.

Lactim - lactam tautomerism. Minor nitrogenous bases (hypoxanthine, 3-N-methyluracil, etc.). Derivatives of nitrogenous bases - antimetabolites (5-fluorouracil, 6-mercaptopurine).

Nucleosides. Definition. Formation of a glycosidic bond between a nitrogenous base and a pentose. Hydrolysis of nucleosides. Nucleosides antimetabolites (adenine arabinoside).

Nucleotides. Definition. Structure. Formation of a phosphoester bond during the esterification of the C5 hydroxyl of pentose with phosphoric acid. Hydrolysis of nucleotides. Macroerg nucleotides (nucleoside polyphosphates - ADP, ATP, etc.). Nucleotides-coenzymes (NAD+, FAD), structure, role of vitamins B5 and B2.

Nucleic acids - RNA and DNA. Definition. Nucleotide composition of RNA and DNA. Primary structure. Phosphodiester bond. Hydrolysis of nucleic acids. Definition of the concepts triplet (codon), gene (cistron), genetic code (genome). International Human Genome Project.

Secondary structure of DNA. The role of hydrogen bonds in the formation of secondary structure. Complementary pairs of nitrogenous bases. Tertiary structure of DNA. Changes in the structure of nucleic acids under the influence of chemicals. The concept of mutagenic substances.

Lipids. Definition, classification. Saponifiable and unsaponifiable lipids.

Natural higher fatty acids are components of lipids. The most important representatives: palmitic, stearic, oleic, linoleic, linolenic, arachidonic, eicosapentaenoic, docosohexaenoic (vitamin F).

Neutral lipids. Acylglycerols - natural fats, oils, waxes.

Artificial edible hydrofats. Biological role of acylglycerols.

Phospholipids. Phosphatidic acids. Phosphatidylcholines, phosphatidiethanolamines and phosphatidylserines. Structure. Participation in the formation of biological membranes. Lipid peroxidation in cell membranes.

Sphingolipids. Sphingosine and sphingomyelins. Glycolipids (cerebrosides, sulfatides and gangliosides).

Unsaponifiable lipids. Terpenes. Mono- and bicyclic terpenes 6 Pharmacological properties Pharmacological properties of some classes of mono-poly and some classes of heterofunctional compounds (hydrogen halides, alcohols, oxy- and organic compounds. oxoacids, benzene derivatives, heterocycles, alkaloids.). Chemical The chemical nature of some of the anti-inflammatory drugs, analgesics, antiseptics and classes of drugs. antibiotics.

6.3. Sections of disciplines and types of classes 1. Introduction to the subject. Classification, nomenclature and research of bioorganic compounds 2. Theoretical foundations of the structure of organic reactivity.

3. Biologically important classes of organic 5 Pharmacological properties of some classes of organic compounds. The chemical nature of some classes of drugs L-lectures; PZ – practical exercises; LR – laboratory work; C – seminars; SRS – independent work of students;

6.4 Thematic plan of lectures on discipline 1 1 Introduction to the subject. History of the development of bioorganic chemistry, significance for 3 2 The theory of the structure of organic compounds by A.M. Butlerov. Isomerism as 4 2 Mutual influence of atoms: causes of occurrence, types and methods of its transmission in 7 1.2 Test work in the sections “Classification, nomenclature and modern physicochemical methods for studying bioorganic compounds” and “Theoretical foundations of the structure of organic compounds and factors determining their reaction 15 5 Pharmacological properties of some classes of organic compounds. Chemical 19 4 14 Detection of insoluble calcium salts of higher carbonates 1 1 Introduction to the subject. Classification and Working with recommended literature.

nomenclature of bioorganic compounds. Completing a written assignment for 3 2 Mutual influence of atoms in molecules Work with recommended literature.

4 2 Acidity and basicity of organic materials Work with recommended literature.

5 2 Mechanisms of organic reactions Work with recommended literature.

6 2 Oxidation and reduction of organic materials Work with recommended literature.

7 1.2 Test work by section Work with recommended literature. * modern physical and chemical methods on the proposed topics, conducting research on bioorganic compounds”, information search in various organic compounds and factors, INTERNET and work with English-language databases 8 3 Heterofunctional bioorganic Work with recommended literature.

9 3 Biologically important heterocycles. Work with recommended literature.

10 3 Vitamins (laboratory work). Work with recommended literature.

12 4 Alpha amino acids, peptides and proteins. Work with recommended literature.

13 4 Nitrogen bases, nucleosides, Work with recommended literature.

nucleotides and nucleic acids. Completing a written writing task 15 5 Pharmacological properties of some Work with recommended literature.

classes of organic compounds. Completing a written assignment to write The chemical nature of some classes of chemical formulas of some medicinal * - tasks of the student's choice.

organic compounds.

organic molecules.

organic molecules.

organic compounds.

organic compounds.

connections. Stereoisomerism.

certain classes of drugs.

During the semester, a student can score a maximum of 65 points in practical classes.

In one practical lesson, a student can score a maximum of 4.3 points. This number consists of points scored for attending a class (0.6 points), completing an assignment for extracurricular independent work (1.0 points), laboratory work (0.4 points) and points awarded for an oral answer and a test task (from 1 .3 to 2.3 points). Points for attending classes, completing assignments for extracurricular independent work and laboratory work are awarded on a “yes” - “no” basis. Points for the oral answer and the test task are awarded differentiated from 1.3 to 2.3 points in the case of positive answers: 0-1.29 points correspond to the rating “unsatisfactory”, 1.3-1.59 - “satisfactory”, 1.6 -1.99 – “good”, 2.0-2.3 – “excellent”. On the test, a student can score a maximum of 5.0 points: attending class 0.6 points and giving an oral answer 2.0-4.4 points.

To be admitted to the test, a student must score at least 45 points, while the student’s current performance is assessed as follows: 65-75 points – “excellent”, 54-64 points – “good”, 45-53 points – “satisfactory”, less than 45 points – unsatisfactory. If a student scores from 65 to 75 points (“excellent” result), then he is exempt from the test and receives a “pass” mark in the grade book automatically, gaining 25 points for the test.

On the test, a student can score a maximum of 25 points: 0-15.9 points correspond to the grade “unsatisfactory”, 16-17.5 – “satisfactory”, 17.6-21.2 – “good”, 21.3-25 – “ Great".

Distribution of bonus points (up to 10 points per semester in total) 1. Lecture attendance – 0.4 points (100% lecture attendance – 6.4 points per semester);

2. Participation in UIRS up to 3 points, including:

writing an abstract on the proposed topic – 0.3 points;

preparation of a report and multimedia presentation for the final educational and theoretical conference 3. Participation in research work – up to 5 points, including:

attending a meeting of the student scientific circle at the department - 0.3 points;

preparing a report for a meeting of the student scientific circle – 0.5 points;

giving a report at a university student scientific conference – 1 point;

presentation at a regional, all-Russian and international student scientific conference – 3 points;

publication in collections of student scientific conferences – 2 points;

publication in a peer-reviewed scientific journal – 5 points;

4. Participation in educational work at the department up to 3 points, including:

participation in the organization of educational activities carried out by the department during extracurricular hours - 2 points for one event;

attending educational activities held by the department during extracurricular hours – 1 point for one event;

Distribution of penalty points (up to 10 points per semester in total) 1. Absence from lectures for an unexcused reason - 0.66-0.67 points (0% attendance at lectures - 10 points for If a student missed a lesson for a valid reason, he has the right to work out the lesson to improve your current rating.

If the absence is unexcused, the student must complete the class and receive a grade with a reduction factor of 0.8.

If a student is exempt from physical presence in classes (by order of the academy), then he is awarded maximum points if he completes extracurricular independent work.

6. Educational, methodological and information support of the discipline 1. N.A. Tyukavkina, Yu.I. Baukov, S.E. Zurabyan. Bioorganic chemistry. M.:DROFA, 2009.

2. Tyukavkina N.A., Baukov Yu.I. Bioorganic chemistry. M.:DROFA, 2005.

1. Ovchinikov Yu.A. Bioorganic chemistry. M.: Education, 1987.

2. Riles A., Smith K., Ward R. Fundamentals of organic chemistry. M.: Mir, 1983.

3. Shcherbak I.G. Biological chemistry. Textbook for medical schools. S.-P. St. Petersburg State Medical University publishing house, 2005.

4. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, 2004.

5. Berezov T.T., Korovkin B.F. Biological chemistry. M.: Medicine, Postupaev V.V., Ryabtseva E.G. Biochemical organization of cell membranes (textbook for students of pharmaceutical faculties of medical universities). Khabarovsk, Far Eastern State Medical University. 2001

7. Soros educational magazine, 1996-2001.

8. Guide to laboratory classes in bioorganic chemistry. Edited by N.A. Tyukavkina, M.:

Medicine, 7.3 Educational and methodological materials prepared by the department 1. Methodological development of practical classes in bioorganic chemistry for students.

2. Methodological developments for independent extracurricular work of students.

3. Borodin E.A., Borodina G.P. Biochemical diagnosis (physiological role and diagnostic value of biochemical parameters of blood and urine). Textbook 4th edition. Blagoveshchensk, 2010.

4. Borodina G.P., Borodin E.A. Biochemical diagnosis (physiological role and diagnostic value of biochemical parameters of blood and urine). Electronic textbook. Blagoveshchensk, 2007.

5. Assignments for computer testing of students’ knowledge in bioorganic chemistry (Compiled by Borodin E.A., Doroshenko G.K., Egorshina E.V.) Blagoveshchensk, 2003.

6. Test assignments in bioorganic chemistry for the exam in bioorganic chemistry for students of the medical faculty of medical universities. Methodical manual. (Compiled by Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.

7. Test assignments in bioorganic chemistry for practical classes in bioorganic chemistry for students of the Faculty of Medicine. Methodical manual. (Compiled by Borodin E.A., Doroshenko G.K.). Blagoveshchensk, 2002.

8. Vitamins. Methodical manual. (Compiled by Egorshina E.V.). Blagoveshchensk, 2001.

8.5 Providing discipline with equipment and educational materials 1 Chemical glassware:

Glassware:

1.1 chemical test tubes 5000 Chemical experiments and analyzes in practical classes, UIRS, 1.2 centrifuge tubes 2000 Chemical experiments and analyzes in practical classes, UIRS, 1.3 glass rods 100 Chemical experiments and analyzes in practical classes, UIRS, 1.4. flasks of various volumes (for 200 Chemical experiments and analyzes in practical classes, UIRS, 1.5 large volume flasks - 0.5-2.0 30 Chemical experiments and analyzes in practical classes, UIRS, 1.6 chemical beakers of various 120 Chemical experiments and analyzes in practical classes, UIRS, 1.7 large chemical beakers 50 Chemical experiments and analyzes in practical classes, UIRS, preparation of workers 1.8 flasks of various sizes 2000 Chemical experiments and analyzes in practical classes, UIRS, 1.9 filter funnels 200 Chemical experiments and analyzes in practical classes, UIRS , 1.10 glassware Chemical experiments and analyzes in practical classes, CIRS, chromatography, etc.).

1.11 alcohol lamps 30 Chemical experiments and analyzes in practical classes, UIRS, Porcelain dishes 1.12 glasses different volumes (0.2- 30 Preparation of reagents for practical classes 1.13 mortars and pestles Preparation of reagents for practical classes, chemical experiments and 1.15 cups for evaporation 20 Chemical experiments and analyzes for practical classes, UIRS, Measuring glassware:

1.16 volumetric flasks of various 100 Preparation of reagents for practical classes, Chemical experiments 1.17 graduated cylinders of various 40 Preparation of reagents for practical classes, Chemical experiments 1.18 beakers of various volumes 30 Preparation of reagents for practical classes, Chemical experiments 1.19 measuring pipettes for 2000 Chemical experiments and analyzes for practical classes, UIRS, micropipettes) 1.20 mechanical automatic 15 Chemical experiments and analyzes in practical classes, UIRS, 1.21 mechanical automatic 2 Chemical experiments and analyzes in practical classes, UIRS, variable volume dispensers NIRS 1.22 electronic automatic 1 Chemical experiments and analyzes in practical classes, UIRS, 1.23 AC microsyringes 5 Chemical experiments and analyzes in practical classes, UIRS, 2 Technical equipment:

2.1 racks for test tubes 100 Chemical experiments and analyzes in practical classes, UIRS, 2.2 racks for pipettes 15 Chemical experiments and analyzes in practical classes, UIRS, 2.3 metal racks 15 Chemical experiments and analyzes in practical classes, UIRS, Heating devices:

2.4 drying cabinets 3 Drying chemical glassware, holding chemicals 2.5 air thermostats 2 Thermostating of the incubation mixture when determining 2.6 water thermostats 2 Thermostating of the incubation mixture when determining 2.7 electric stoves 3 Preparation of reagents for practical exercises, chemical experiments and 2.8 Refrigerators with freezers 5 Storage of chemical reagents, solutions and biological material for chambers “Chinar”, “Biryusa”, practical exercises , UIRS, NIRS "Stinol"

2.9 Storage cabinets 8 Storage of chemical reagents 2.10 Metal safe 1 Storage of toxic reagents and ethanol 3 General purpose equipment:

10 Temperature control during chemical analyzes 3.11 Set of hydrometers 1 Measuring the density of solutions 4 Special-purpose equipment:

4.1 Apparatus for electrophoresis at 1 Demonstration of the method of electrophoresis of serum proteins at 4.2 Apparatus for electrophoresis at 1 Demonstration of the method for separating serum lipoproteins 4.3 Equipment for column Demonstration of the method for separating proteins using chromatography 4.4 Equipment for Demonstration of the TLC method for separating lipids at practical thin chromatography layer. classes, NIRS Measuring equipment:

Photoelectric colorimeters:

4.8 Photometer “SOLAR” 1 Measurement of light absorption of colored solutions at 4.9 Spectrophotometer SF 16 1 Measurement light absorption of solutions in the visible and UV regions 4.10 Clinical spectrophotometer 1 Measurement of light absorption of solutions in the visible and UV regions of the “Schimadzu - CL–770” spectrum using spectral methods of determination 4.11 Highly efficient 1 Demonstration of the HPLC method (practical exercises, UIRS, NIRS) liquid chromatograph "Milichrome - 4".

4.12 Polarimeter 1 Demonstration of the optical activity of enantiomers, 4.13 Refractometer 1 Demonstration refractometric method of determination 4.14 pH meters 3 Preparation of buffer solutions, demonstration of buffer 5 Projection equipment:

5.1 Multimedia projector and 2 Demonstration of multimedia presentations, photo and overhead projectors: Demonstration slides during lectures and practical classes 5.3 “Semi-automatic bearing” 5.6 Device for demonstration Assigned to the morphological educational building. Demonstration of transparent films (overhead) and illustrative material at lectures, during UIRS and NIRS film projector.

6 Computer technology:

6.1 Departmental network of 1 Access to educational resources of the INTERNET (national and personal computers with international electronic databases on chemistry, biology and access to INTERNET medicine) for teachers of the department and students in educational and 6.2 Personal computers 8 Creation by teachers of the department of printed and electronic staff of the department didactic materials during educational and methodological work, 6.3 Computer class for 10 1 Programmed testing of students’ knowledge in practical classes, during tests and exams (current, 7 Educational tables:

1. Peptide bond.

2. Regularity of the structure of the polypeptide chain.

3. Types of bonds in a protein molecule.

4. Disulfide bond.

5. Species specificity of proteins.

6. Secondary structure of proteins.

7. Tertiary structure of proteins.

8. Myoglobin and hemoglobin.

9. Hemoglobin and its derivatives.

10. Blood plasma lipoproteins.

11. Types of hyperlipidemia.

12. Electrophoresis of proteins on paper.

13. Scheme of protein biosynthesis.

14. Collagen and tropocollagen.

15. Myosin and actin.

16. Vitamin deficiency RR (pellagra).

17. Vitamin B1 deficiency.

18. Vitamin deficiency C.

19. Vitamin deficiency A.

20. Vitamin deficiency D (rickets).

21. Prostaglandins are physiologically active derivatives of unsaturated fatty acids.

22. Neuroxins formed from catechalamines and indolamines.

23. Products of non-enzymatic reactions of dopamine.

24. Neuropeptides.

25. Polyunsaturated fatty acids.

26. Interaction of liposomes with the cell membrane.

27. Free oxidation (differences from tissue respiration).

28. PUFAs of the omega 6 and omega 3 families.

2 Sets of slides for various sections of the program 8.6 Interactive learning tools (Internet technologies), multimedia materials, Electronic libraries and textbook, photo and video materials 1 Interactive learning tools (Internet technologies) 2 Multimedia materials Stonik V.A. (TIBOH DSC SB RAS) “Natural compounds are the basis 5 Borodin E.A. (AGMA) “The human genome. Genomics, proteomics and Author's presentation 6 Pivovarova E.N (Institute of Cytology and Genetics, Siberian Branch of the Russian Academy of Medical Sciences) “The role of regulation of gene expression Author’s presentation of a person.”

3 Electronic libraries and textbooks:

2 MEDLINE. CD version of electronic databases on chemistry, biology and medicine.

3 Life Sciences. CD version of electronic databases on chemistry and biology.

4 Cambridge Scientific Abstracts. CD version of electronic databases on chemistry and biology.

5 PubMed - electronic database of the National Institute of Health http://www.ncbi.nlm.nih.gov/pubmed/ Organic chemistry. Electronic library. (Compiled by N.F. Tyukavkina, A.I. Khvostova) - M., 2005.

Organic and general chemistry. Medicine. Lectures for students, course. (Electronic manual). M., 2005

4 Videos:

3 MES TIBOKH DSC FEB RAS CD

Author's photos and video materials of the head. department prof. E.A. Borodin about 1 universities of Uppsala (Sweden), Granada (Spain), medical schools of universities in Japan (Niigata, Osaka, Kanazawa, Hirosaki), IBMH RAMS, Institute of Physics and Chemistry of the Ministry of Health of Russia, TIBOKHE DSC. FEB RAS.

8.1. Examples of current control test items (with standard answers) for lesson No. 4 “Acidity and basicity organic molecules"

1. Select the characteristic features of Bronsted-Lowry acids:

1. increase the concentration of hydrogen ions in aqueous solutions 2. increase the concentration of hydroxide ions in aqueous solutions 3. are neutral molecules and ions - proton donors 4. are neutral molecules and ions - proton acceptors 5. do not affect the reaction of the medium 2. Specify the factors , affecting the acidity of organic molecules:

1. electronegativity of the heteroatom 2. polarizability of the heteroatom 3. nature of the radical 4. ability to dissociate 5. solubility in water 3. Select the strongest Bronsted acids from the listed compounds:

1. alkanes 2. amines 3. alcohols 4. thiols 5. carboxylic acids 4. Indicate the characteristic features of organic compounds that have the properties of bases:

1. proton acceptors 2. proton donors 3. upon dissociation give hydroxyl ions 4. do not dissociate 5. basic properties determine reactivity 5. Select the weakest base from the given compounds:

1. ammonia 2. methylamine 3. phenylamine 4. ethylamine 5. propylamine 8.2 Examples of situational tasks of current control (with answer standards) 1. Determine the parent structure in the compound:

Solution. The choice of parent structure in the structural formula of an organic compound is regulated in the IUPAC substitutive nomenclature by a number of consistently applied rules (see Textbook, 1.2.1).

Each subsequent rule is applied only when the previous one does not allow making a clear choice. Compound I contains aliphatic and alicyclic fragments. According to the first rule, the structure with which the senior characteristic group is directly related is chosen as the parent structure. Of the two characteristic groups present in compound I (OH and NH), the hydroxyl group is the oldest. Therefore, the initial structure will be cyclohexane, which is reflected in the name of this compound - 4-aminomethylcyclohexanol.

2. The basis of a number of biologically important compounds and drugs is a condensed heterocyclic purine system, including pyrimidine and imidazole nuclei. What explains the increased resistance of purine to oxidation?

Solution. Aromatic compounds have high conjugation energy and thermodynamic stability. One of the manifestations of aromatic properties is resistance to oxidation, although “externally”

aromatic compounds have a high degree of unsaturation, which usually makes them prone to oxidation. To answer the question posed in the problem statement, it is necessary to establish whether purine belongs to aromatic systems.

According to the definition of aromaticity, a necessary (but not sufficient) condition for the emergence of a conjugated closed system is the presence in the molecule of a flat cyclic skeleton with a single electron cloud. In the purine molecule, all carbon and nitrogen atoms are in a state of sp2 hybridization, and therefore all the bonds lie in the same plane. Due to this, the orbitals of all atoms included in the cycle are located perpendicular to the skeletal plane and parallel to each other, which creates conditions for their mutual overlap with the formation of a single closed delocalized ti-electronic system covering all the atoms of the cycle (circular conjugation).

Aromaticity is also determined by the number of -electrons, which must correspond to the formula 4/7 + 2, where n is a series of natural numbers O, 1, 2, 3, etc. (Hückel's rule). Each carbon atom and the pyridine nitrogen atoms in positions 1, 3 and 7 contribute one p-electron to the conjugated system, and the pyrrole nitrogen atom in position 9 contributes a lone pair of electrons. The conjugated purine system contains 10 electrons, which corresponds to Hückel's rule at n = 2.

Thus, the purine molecule has an aromatic character and its resistance to oxidation is associated with this.

The presence of heteroatoms in the purine cycle leads to uneven distribution of electron density. Pyridine nitrogen atoms exhibit an electron-withdrawing character and reduce the electron density on carbon atoms. In this regard, the oxidation of purine, generally considered as the loss of electrons by the oxidizing compound, will be even more difficult compared to benzene.

8.3 Test tasks for testing (one option in full with answer standards) 1.Name the organogenic elements:

7.Si 8.Fe 9.Cu 2.Indicate functional groups that have a Pi bond:

1.Carboxyl 2.amino group 3.hydroxyl 4.oxo group 5.carbonyl 3.Indicate the senior functional group:

1.-C=O 2.-SO3H 3.-CII 4.-COOH 5.-OH 4.Which class of organic compounds does lactic acid CH3-CHOH-COOH, formed in tissues as a result of the anaerobic breakdown of glucose, belong to?

1.Carboxylic acids 2.Hydroxy acids 3.Amino acids 4.Keto acids 5.Name by substitution nomenclature the substance that is the main energy fuel of the cell and has the following structure:

CH2-CH -CH -CH -CH -C=O

I I III I

OH OH OH OH OH H

1. Equalization of the electron density of sigma and pi bonds 2. Stability and low reactivity 3. Instability and high reactivity 4. Contain alternating sigma and pi bonds 5. Pi bonds are separated by -CH2 groups 7. For which compounds characteristic Pi-Pi conjugation:

1. carotenes and vitamin A 2. pyrrole 3. pyridine 4. porphyrins 5. benzopyrene 8. Select substituents of the first kind that orient to the ortho- and para-positions:

1.alkyl 2.- OH 3.- NH 4.- COOH 5.- SO3H 9. What effect does the -OH group have in aliphatic alcohols:

1. Positive inductive 2. Negative inductive 3. Positive mesomeric 4. Negative mesomeric 5. The type and sign of the effect depend on the position of the -OH group 10. Select the radicals that have a negative mesomeric effect 1. Halogens 2. Alkyl radicals 3. Amino group 4. Hydroxy group 5. Carboxy group 11. Select the characteristic features of Bronsted-Lowry acids:

1. increase the concentration of hydrogen ions in aqueous solutions 2. increase the concentration of hydroxide ions in aqueous solutions 3. are neutral molecules and ions - proton donors 4. are neutral molecules and ions - proton acceptors 5. do not affect the reaction of the medium 12. Specify the factors , affecting the acidity of organic molecules:

1. electronegativity of the heteroatom 2. polarizability of the heteroatom 3. nature of the radical 4. ability to dissociate 5. solubility in water 13. Select the strongest Bronsted acids from the listed compounds:

1. alkanes 2. amines 3. alcohols 4. thiols 5. carboxylic acids 14. Indicate the characteristic features of organic compounds that have the properties of bases:

1. proton acceptors 2. proton donors 3. upon dissociation they give hydroxyl ions 4. do not dissociate 5. basic properties determine reactivity 15. Select the weakest base from the given compounds:

1. ammonia 2. methylamine 3. phenylamine 4. ethylamine 5. propylamine 16. What features are used to classify reactions of organic compounds:

1. The mechanism of breaking a chemical bond 2. The final result of the reaction 3. The number of molecules participating in the stage that determines the rate of the entire process 4. The nature of the reagent attacking the bond 17. Select the active forms of oxygen:

1. singlet oxygen 2. peroxide diradical -O-O-Superoxide ion 4. hydroxyl radical 5. triplet molecular oxygen 18. Select the characteristic features of electrophilic reagents:

1.particles that carry a partial or complete positive charge 2.are formed by the homolytic cleavage of a covalent bond 3.particles that carry an unpaired electron 4.particles that carry a partial or complete negative charge 5.are formed by the heterolytic cleavage of a covalent bond 19.Select compounds for which Characteristic reactions are electrophilic substitution:

1. alkenes 2. arenes 3. alkadienes 4. aromatic heterocycles 5. alkanes 20. Indicate the biological role of free radical oxidation reactions:

1. phagocytic activity of cells 2. universal mechanism of destruction of cell membranes 3. self-renewal of cellular structures 4. play a decisive role in the development of many pathological processes 21. Select which classes of organic compounds are characterized by nucleophilic substitution reactions:

1. alcohols 2. amines 3. halogen derivatives of hydrocarbons 4. thiols 5. aldehydes 22. In what order does the reactivity of substrates decrease in nucleophilic substitution reactions:

1. halogen derivatives of hydrocarbons, amine alcohols 2. amine alcohols, halogen derivatives of hydrocarbons 3. amine alcohols, halogen derivatives of hydrocarbons 4. halogen derivatives of hydrocarbons, amine alcohols 23. Select polyhydric alcohols from the listed compounds:

1. ethanol 2. ethylene glycol 3. glycerol 4. xylitol 5. sorbitol 24. Choose what is characteristic of this reaction:

CH3-CH2OH --- CH2=CH2 + H2O 1. elimination reaction 2. intramolecular dehydration reaction 3. occurs in the presence of mineral acids when heated 4. occurs under normal conditions 5. intermolecular dehydration reaction 25. What properties appear when an organic substance is introduced into a molecule chlorine substances:

1. narcotic properties 2. lachrymatory (tearing) 3. antiseptic properties 26. Select the reactions characteristic of the SP2-hybridized carbon atom in oxo compounds:

1. nucleophilic addition 2. nucleophilic substitution 3. electrophilic addition 4. homolytic reactions 5. heterolytic reactions 27. In what order does the ease of nucleophilic attack of carbonyl compounds decrease:

1. aldehydes ketones anhydrides esters amides salts of carboxylic acids 2. ketones aldehydes anhydrides esters amides salts of carboxylic acids 3. anhydrides aldehydes ketones esters amides salts of carboxylic acids 28. Determine what is characteristic of this reaction:

1.qualitative reaction to aldehydes 2.aldehyde is a reducing agent, silver oxide (I) is an oxidizing agent 3.aldehyde is an oxidizing agent, silver oxide (I) is a reducing agent 4.redox reaction 5.occurs in an alkaline medium 6.characteristic of ketones 29 .Which of the following carbonyl compounds undergo decarboxylation to form biogenic amines?

1. carboxylic acids 2. amino acids 3. oxo acids 4. hydroxy acids 5. benzoic acid 30. How do acid properties change in the homologous series of carboxylic acids:

1. increase 2. decrease 3. do not change 31. Which of the proposed classes of compounds are heterofunctional:

1. hydroxy acids 2. oxo acids 3. amino alcohols 4. amino acids 5. dicarboxylic acids 32. Hydroxy acids include:

1. citric 2. butyric 3. acetoacetic 4. pyruvic 5. malic 33. Select medications - derivatives of salicylic acid:

1. paracetamol 2. phenacetin 3. sulfonamides 4. aspirin 5. PAS 34. Select drugs - p-aminophenol derivatives:

1. paracetamol 2. phenacetin 3. sulfonamides 4. aspirin 5. PAS 35. Select drugs - sulfanilic acid derivatives:

1. paracetamol 2. phenacetin 3. sulfonamides 4. aspirin 5. PASK 36. Select the main provisions of the theory of A.M. Butlerov:

1. carbon atoms are connected by simple and multiple bonds 2. carbon in organic compounds is tetravalent 3. the functional group determines the properties of the substance 4. carbon atoms form open and closed cycles 5. in organic compounds carbon is in a reduced form 37. Which isomers are classified as spatial:

1. chains 2. position of multiple bonds 3. functional groups 4. structural 5. configurational 38. Choose what is characteristic of the concept “conformation”:

1. the possibility of rotation around one or more sigma bonds 2. conformers are isomers 3. a change in the sequence of bonds 4. a change in the spatial arrangement of substituents 5. a change in the electronic structure 39. Choose the similarity between enantiomers and diastereomers:

1. have the same physicochemical properties 2. are able to rotate the plane of polarization of light 3. are not able to rotate the plane of polarization of light 4. are stereoisomers 5. are characterized by the presence of a center of chirality 40. Select the similarity between configurational and conformational isomerism:

1. Isomerism is associated with different positions in space of atoms and groups of atoms 2. Isomerism is due to the rotation of atoms or groups of atoms around a sigma bond 3. Isomerism is due to the presence of a center of chirality in the molecule 4. Isomerism is due to different arrangements of substituents relative to the pi bond plane.

41.Name the heteroatoms that make up biologically important heterocycles:

1.nitrogen 2.phosphorus 3.sulfur 4.carbon 5.oxygen 42.Indicate the 5-membered heterocycle that is part of porphyrins:

1.pyrrolidine 2.imidazole 3.pyrrole 4.pyrazole 5.furan 43.Which heterocycle with one heteroatom is part of nicotinic acid:

1. purine 2. pyrazole 3. pyrrole 4. pyridine 5. pyrimidine 44. Name the final product of purine oxidation in the body:

1. hypoxanthine 2. xanthine 3. uric acid 45. Specify opium alkaloids:

1. strychnine 2. papaverine 4. morphine 5. reserpine 6. quinine 6. What oxidation reactions are characteristic of the human body:

1.dehydrogenation 2.addition of oxygen 3.donation of electrons 4.addition of halogens 5.interaction with potassium permanganate, nitric and perchloric acids 47.What determines the degree of oxidation of a carbon atom in organic compounds:

1. the number of its bonds with atoms of elements more electronegative than hydrogen 2. the number of its bonds with oxygen atoms 3. the number of its bonds with hydrogen atoms 48. What compounds are formed during the oxidation of the primary carbon atom?

1. primary alcohol 2. secondary alcohol 3. aldehyde 4. ketone 5. carboxylic acid 49. Determine what is characteristic of oxidase reactions:

1. oxygen is reduced to water 2. oxygen is included in the composition of the oxidized molecule 3. oxygen goes to the oxidation of hydrogen split off from the substrate 4. reactions have an energetic value 5. reactions have a plastic value 50. Which of the proposed substrates is oxidized more easily in the cell and why?

1. glucose 2. fatty acid 3. contains partially oxidized carbon atoms 4. contains fully hydrogenated carbon atoms 51. Select aldoses:

1. glucose 2. ribose 3. fructose 4. galactose 5. deoxyribose 52. Select the reserve forms of carbohydrates in a living organism:

1. fiber 2. starch 3. glycogen 4. hyaluric acid 5. sucrose 53. Select the most common monosaccharides in nature:

1. trioses 2. tetroses 3. pentoses 4. hexoses 5. heptoses 54. Select amino sugars:

1. beta-ribose 2. glucosamine 3. galactosamine 4. acetylgalactosamine 5. deoxyribose 55. Select the products of monosaccharide oxidation:

1. glucose-6-phosphate 2. glyconic (aldonic) acids 3. glycuronic (uronic) acids 4. glycosides 5. esters 56. Select disaccharides:

1. maltose 2. fiber 3. glycogen 4. sucrose 5. lactose 57. Select homopolysaccharides:

1. starch 2. cellulose 3. glycogen 4. dextran 5. lactose 58. Select which monosaccharides are formed during the hydrolysis of lactose:

1.beta-D-galactose 2.alpha-D-glucose 3.alpha-D-fructose 4.alpha-D-galactose 5.alpha-D-deoxyribose 59. Choose what is characteristic of cellulose:

1. linear, plant polysaccharide 2. structural unit is beta-D-glucose 3. necessary for normal nutrition, is a ballast substance 4. the main carbohydrate in humans 5. does not break down in the gastrointestinal tract 60. Select the carbohydrate derivatives that make up muramin:

1.N-acetylglucosamine 2.N-acetylmuramic acid 3.glucosamine 4.glucuronic acid 5.ribulose-5-phosphate 61.Choose the correct statements from the following: Amino acids are...

1. compounds containing both amino and hydroxy groups in the molecule 2. compounds containing hydroxyl and carboxyl groups 3. are derivatives of carboxylic acids in the radical of which hydrogen is replaced by an amino group 4. compounds containing oxo and carboxyl groups in the molecule 5. compounds containing hydroxy and aldehyde groups 62. How are amino acids classified?

1. by the chemical nature of the radical 2. by physicochemical properties 3. by the number of functional groups 4. by the degree of unsaturation 5. by the nature of additional functional groups 63. Select an aromatic amino acid:

1. glycine 2. serine 3. glutamic 4. phenylalanine 5. methionine 64. Select an amino acid that exhibits acidic properties:

1. leucine 2. tryptophan 3. glycine 4. glutamic 5. alanine 65. Select a basic amino acid:

1. serine 2. lysine 3. alanine 4. glutamine 5. tryptophan 66. Select purine nitrogenous bases:

1. thymine 2. adenine 3. guanine 4. uracil 5. cytosine 67. Select pyrimidine nitrogenous bases:

1.uracil 2.thymine 3.cytosine 4.adenine 5.guanine 68.Select the components of the nucleoside:

1.purine nitrogenous bases 2.pyrimidine nitrogenous bases 3.ribose 4.deoxyribose 5.phosphoric acid 69.Indicate the structural components of nucleotides:

1. purine nitrogenous bases 2. pyrimidine nitrogenous bases 3. ribose 4. deoxyribose 5. phosphoric acid 70. Indicate the distinctive features of DNA:

1. formed by one polynucleotide chain 2. formed by two polynucleotide chains 3. contains ribose 4. contains deoxyribose 5. contains uracil 6. contains thymine 71. Select saponifiable lipids:

1. neutral fats 2. triacylglycerols 3. phospholipids 4. sphingomyelins 5. steroids 72. Select unsaturated fatty acids:

1. palmitic 2. stearic 3. oleic 4. linoleic 5. arachidonic 73. Specify the characteristic composition of neutral fats:

1.mericyl alcohol + palmitic acid 2.glycerol + butyric acid 3.sphingosine + phosphoric acid 4.glycerol + higher carboxylic acid + phosphoric acid 5.glycerol + higher carboxylic acids 74. Choose what function phospholipids perform in the human body:

1. regulatory 2. protective 3. structural 4. energetic 75. Select glycolipids:

1.phosphatidylcholine 2.cerebrosides 3.sphingomyelins 4.sulfatides 5.gangliosides

ANSWERS TO TEST TASKS

3. The ability to isolate functional groups, acidic and basic centers, conjugated and aromatic fragments in molecules to determine chemical behavior 4. The ability to predict the direction and result of organic chemical transformations 5. Possession of the skills of independent work with educational, scientific and reference literature; conduct a search and draw general conclusions.

6. Possession of skills in handling chemical glassware.

7. Possession of safe work skills in a chemical laboratory and the ability to handle caustic, poisonous, highly volatile organic compounds, work with burners, alcohol lamps and electric heating devices.

1. Subject and tasks of bioorganic chemistry. Implications in medical education.

2. The elemental composition of organic compounds, as the reason for their compliance with biological processes.

3. Classification of organic compounds. Classes, general formulas, functional groups, individual representatives.

4. Nomenclature of organic compounds. Trivial names. Substitute IUPAC nomenclature.

5. Main functional groups. Parental structure. Deputies. Seniority of groups, deputies. Names of functional groups and substituents as prefixes and endings.

6. Theoretical foundations of the structure of organic compounds. Theory of A.M. Butlerov.

Structural formulas. Structural isomerism. Chain and position isomers.

7. Spatial structure of organic compounds. Stereochemical formulas.

Molecular models. The most important concepts in stereochemistry are the configuration and conformation of organic molecules.

8. Conformations of open chains - eclipsed, inhibited, oblique. Energy and reactivity of different conformations.

9. Conformations of cycles using the example of cyclohexane (chair and bath). Axial and equatorial connections.

10. Mutual influence of atoms in molecules of organic compounds. Its causes, types of manifestation. Influence on the reactivity of molecules.

11.Pairing. Conjugate systems, conjugate connections. Pi-pi conjugation in dienes. Conjugation energy. Stability of coupled systems (vitamin A).

12. Pairing in arenas (pi-pi pairing). Aromaticity. Hückel's rule. Benzene, naphthalene, phenanthrene. Reactivity of the benzene ring.

13. Conjugation in heterocycles (p-pi and pi-pi conjugation using the example of pyrrole and pyridine).

Stability of heterocycles - biological significance using the example of tetrapyrrole compounds.

14.Polarization of bonds. Reasons. Polarization in alcohols, phenols, carbonyl compounds, thiols. Influence on the reactivity of molecules.\ 15.Electronic effects. Inductive effect in molecules containing sigma bonds. Sign of the inductive effect.

16.Mesomeric effect in open chains with conjugated pi bonds using the example of 1,3 butadiene.

17.Mesomeric effect in aromatic compounds.

18.Electron-donating and electron-withdrawing substituents.

19. Deputies of the 1st and 2nd kind. Rule of orientation in the benzene ring.

20.Acidity and basicity of organic compounds. Brendstet-Lowry acids and bases.

Acid-base pairs are conjugate acids and bases. Ka and pKa are quantitative characteristics of the acidity of organic compounds. The importance of acidity for the functional activity of organic molecules.

21.Acidity of various classes of organic compounds. Factors that determine the acidity of organic compounds are the electronegativity of the non-metal atom bonded to hydrogen, the polarizability of the non-metal atom, the nature of the radical bonded to the non-metal atom.

22.Organic bases. Amines. Reason for basicity. The influence of radicals on the basicity of aliphatic and aromatic amines.

23. Classification of reactions of organic compounds according to their mechanism. Concepts of homolytic and heterolytic reactions.

24. Radical substitution reactions in alkanes. Free radical oxidation in living organisms. Reactive oxygen species.

25. Electrophilic addition in alkenes. Formation of Pi-complexes, carbocations. Reactions of hydration, hydrogenation.

26.Electrophilic substitution in the aromatic ring. Formation of intermediate sigma complexes. Benzene bromination reaction.

27.Nucleophilic substitution in alcohols. Reactions of dehydration, oxidation of primary and secondary alcohols, formation of esters.

28.Nucleophilic addition of carbonyl compounds. Biologically important reactions of aldehydes: oxidation, formation of hemiacetals when interacting with alcohols.

29.Nucleophilic substitution in carboxylic acids. Biologically important reactions of carboxylic acids.

30. Oxidation of organic compounds, biological significance. The degree of oxidation of carbon in organic molecules. Oxidability of different classes of organic compounds.

31.Energetic oxidation. Oxidase reactions.

32.Non-energetic oxidation. Oxygenase reactions.

33. The role of free radical oxidation in the bactericidal action of phagocytic cells.

34. Restoration of organic compounds. Biological significance.

35.Multifunctional compounds. Polyhydric alcohols - ethylene glycol, glycerin, xylitol, sorbitol, inositol. Biological significance. Biologically important reactions of glycerol are oxidation and formation of esters.

36.Dibasic dicarboxylic acids: oxalic, malonic, succinic, glutaric.

The conversion of succinic acid to fumaric acid is an example of biological dehydrogenation.

37. Amines. Classification:

By the nature of the radical (aliphatic and aromatic); -by the number of radicals (primary, secondary, tertiary, quaternary ammonium bases); -by the number of amino groups (mono- and diamines-). Diamines: putrescine and cadaverine.

38. Heterofunctional compounds. Definition. Examples. Features of the manifestation of chemical properties.

39. Amino alcohols: ethanolamine, choline, acetylcholine. Biological significance.

40.Hydroxyacids. Definition. General formula. Classification. Nomenclature. Isomerism.

Representatives of monocarboxylic hydroxy acids: lactic, beta-hydroxybutyric, gamma-xibutyric;

dicarbonate: apple, wine; tricarboxylic: lemon; aromatic: salicylic.

41. Chemical properties of hydroxy acids: by carboxyl, by hydroxyl group, dehydration reactions of alpha, beta and gamma isomers, difference in reaction products (lactides, unsaturated acids, lactones).

42.Stereoisomerism. Enantiomers and diastereomers. Chirality of molecules of organic compounds as a cause of optical isomerism.

43. Enantiomers with one chirality center (lactic acid). Absolute and relative configuration of enantiomers. Oxyacid key. D and L glyceraldehyde. D and L isomers.

Racemates.

44. Enantiomers with several centers of chirality. Tartaric and mesotartaric acids.

45.Stereoisomerism and biological activity of stereoisomers.

46.Cis-and trans-isomerism using the example of fumaric and maleic acids.

47.Oxoacids. Definition. Biologically important representatives: pyruvic acid, acetoacetic acid, oxaloacetic acid. Ketoenol tautomerism using the example of pyruvic acid.

48. Amino acids. Definition. General formula. Isomers of amino group position (alpha, beta, gamma). Biological significance of alpha amino acids. Representatives of beta-, gamma- and other isomers (beta-aminopropionic, gamma-aminobutyric, epsilonaminocaproic). Dehydration reaction of gamma isomers with the formation of cyclic lactones.

49. Heterofunctional benzene derivatives as the basis of medicines. Derivatives of p-aminobenzoic acid - PABA (folic acid, anesthesin). PABA antagonists are sulfanilic acid derivatives (sulfonamides - streptocide).

50. Heterofunctional benzene derivatives - medicines. Raminophenol derivatives (paracetamol), salicylic acid derivatives (acetylsalicylic acid). Raminosalicylic acid - PAS.

51.Biologically important heterocycles. Definition. Classification. Features of structure and properties: conjugation, aromaticity, stability, reactivity. Biological significance.

52. Five-membered heterocycles with one heteroatom and their derivatives. Pyrrole (porphin, porphyrins, heme), furan (medicines), thiophene (biotin).

53. Five-membered heterocycles with two heteroatoms and their derivatives. Pyrazole (5-oxo derivatives), imidazole (histidine), thiazole (vitamin B1-thiamine).

54. Six-membered heterocycles with one heteroatom and their derivatives. Pyridine (nicotinic acid - participation in redox reactions, vitamin B6-pyridoxal), quinoline (5-NOK), isoquinoline (alkaloids).

55. Six-membered heterocycles with two heteroatoms. Pyrimidine (cytosine, uracil, thymine).

56.Fused heterocycles. Purine (adenine, guanine). Purine oxidation products hypoxanthine, xanthine, uric acid).

57. Alkaloids. Definition and general characteristics. The structure of nicotine and caffeine.

58.Carbohydrates. Definition. Classification. Functions of carbohydrates in living organisms.

59.Monosugars. Definition. Classification. Representatives.

60.Pentoses. Representatives are ribose and deoxyribose. Structure, open and cyclic formulas. Biological significance.

61.Hexoses. Aldoses and ketoses. Representatives.

62.Open formulas of monosaccharides. Determination of stereochemical configuration. Biological significance of the configuration of monosaccharides.

63. Formation of cyclic forms of monosaccharides. Glycosidic hydroxyl. Alpha and beta anomers. Haworth's formulas.

64. Derivatives of monosaccharides. Phosphorus esters, glyconic and glycuronic acids, amino sugars and their acetyl derivatives.

65. Maltose. Composition, structure, hydrolysis and significance.

66.Lactose. Synonym. Composition, structure, hydrolysis and significance.

67.Sucrose. Synonyms. Composition, structure, hydrolysis and significance.

68. Homopolysaccharides. Representatives. Starch, structure, properties, hydrolysis products, significance.

69.Glycogen. Structure, role in the animal body.

70. Fiber. Structure, role in plants, significance for humans.

72. Heteropolysaccharides. Synonyms. Functions. Representatives. Structural features: dimer units, composition. 1,3- and 1,4-glycosidic bonds.

73.Hyaluronic acid. Composition, structure, properties, significance in the body.

74.Chondroitin sulfate. Composition, structure, significance in the body.

75.Muramin. Composition, meaning.

76. Alpha amino acids. Definition. General formula. Nomenclature. Classification. Individual representatives. Stereoisomerism.

77. Chemical properties of alpha amino acids. Amphotericity, decarboxylation reactions, deamination, hydroxylation in the radical, peptide bond formation.

78.Peptides. Individual peptides. Biological role.

79. Squirrels. Functions of proteins. Levels of structure.

80. Nitrogen bases of nucleic acids - purines and pyrimidines. Modified nitrogenous bases - antimetabolites (fluorouracil, mercaptopurine).

81.Nucleosides. Nucleoside antibiotics. Nucleotides. Mononucleotides in the composition of nucleic acids and free nucleotides are coenzymes.

82. Nucleic acids. DNA and RNA. Biological significance. Formation of phosphodiester bonds between mononucleotides. Levels of nucleic acid structure.

83. Lipids. Definition. Biological role. Classification.

84.Higher carboxylic acids - saturated (palmitic, stearic) and unsaturated (oleic, linoleic, linolenic and arachidonic).

85. Neutral fats - acylglycerols. Structure, meaning. Animal and vegetable fats.

Hydrolysis of fats - products, meaning. Hydrogenation of vegetable oils, artificial fats.

86. Glycerophospholipids. Structure: phosphatidic acid and nitrogenous bases.

Phosphatidylcholine.

87. Sphingolipids. Structure. Sphingosine. Sphingomyelin.

88.Steroids. Cholesterol - structure, meaning, derivatives: bile acids and steroid hormones.

89.Terpenes and terpenoids. Structure and biological significance. Representatives.

90.Fat-soluble vitamins. General characteristics.

91. Anesthesia. Diethyl ether. Chloroform. Meaning.

92. Drugs that stimulate metabolic processes.

93. Sulfonamides, structure, significance. White streptocid.

94. Antibiotics.

95. Anti-inflammatory and antipyretic drugs. Paracetamol. Structure. Meaning.

96. Antioxidants. Characteristic. Meaning.

96. Thiols. Antidotes.

97. Anticoagulants. Characteristic. Meaning.

98. Barbiturates. Characteristic.

99. Analgesics. Meaning. Examples. Acetylsalicylic acid (aspirin).

100. Antiseptics. Meaning. Examples. Furacilin. Characteristic. Meaning.

101. Antiviral drugs.

102. Diuretics.

103. Means for parenteral nutrition.

104. PABC, PASK. Structure. Characteristic. Meaning.

105. Iodoform. Xeroform.Meaning.

106. Poliglyukin. Characteristic. Value 107.Formalin. Characteristic. Meaning.

108. Xylitol, sorbitol. Structure, meaning.

109. Resorcinol. Structure, meaning.

110. Atropine. Meaning.

111. Caffeine. Structure. Value 113. Furacilin. Furazolidone. Characteristic.Value.

114. GABA, GHB, succinic acid.. Structure. Meaning.

115. Nicotinic acid. Structure, meaning

“ … There were so many amazing incidents,

That nothing seemed at all possible to her now ”

L. Carroll "Alice in Wonderland"

Bioorganic chemistry developed on the border between two sciences: chemistry and biology. Currently, medicine and pharmacology have joined them. All four of these sciences use modern methods of physical research, mathematical analysis and computer modeling.

In 1807 J.Ya. Berzelius proposed that substances like olive oil or sugar, which are common in living nature, should be called organic.

By this time, many natural compounds were already known, which later began to be defined as carbohydrates, proteins, lipids, and alkaloids.

In 1812, a Russian chemist K.S. Kirchhoff converted starch by heating it with acid into sugar, later called glucose.

In 1820, a French chemist A. Braconno, by treating protein with gelatin, he obtained the substance glycine, which belongs to a class of compounds that later Berzelius named amino acids.

The birth date of organic chemistry can be considered the work published in 1828 F. Velera, who was the first to synthesize a substance of natural origin – urea- from the inorganic compound ammonium cyanate.

In 1825, the physicist Faraday isolated benzene from a gas that was used to illuminate the city of London. The presence of benzene may explain the smoky flames of London lamps.

In 1842 N.N. Zinin carried out synthe z aniline,

In 1845 A.V. Kolbe, a student of F. Wöhler, synthesized acetic acid - undoubtedly a natural organic compound - from starting elements (carbon, hydrogen, oxygen)

In 1854 P. M. Bertlot heated glycerin with stearic acid and obtained tristearin, which turned out to be identical to the natural compound isolated from fats. Next P.M. Berthelot took other acids that were not isolated from natural fats and obtained compounds very similar to natural fats. With this, the French chemist proved that it is possible to obtain not only analogues of natural compounds, but also create new ones, similar and at the same time different from natural ones.

Many major achievements in organic chemistry in the second half of the 19th century are associated with the synthesis and study of natural substances.

In 1861, the German chemist Friedrich August Kekule von Stradonitz (always called simply Kekule in scientific literature) published a textbook in which he defined organic chemistry as the chemistry of carbon.

During the period 1861-1864. Russian chemist A.M. Butlerov created a unified theory of the structure of organic compounds, which made it possible to transfer all existing achievements to a single scientific basis and opened the way to the development of the science of organic chemistry.

During the same period, D.I. Mendeleev. known throughout the world as a scientist who discovered and formulated the periodic law of changes in the properties of elements, published the textbook “Organic Chemistry”. We have at our disposal its 2nd edition (corrected and expanded, Publication of the Partnership “Public Benefit”, St. Petersburg, 1863. 535 pp.)

In his book, the great scientist clearly defined the connection between organic compounds and vital processes: “We can reproduce many of the processes and substances that are produced by organisms artificially, outside the body. Thus, protein substances, being destroyed in animals under the influence of oxygen absorbed by the blood, are converted into ammonium salts, urea, mucus sugar, benzoic acid and other substances usually excreted in urine... Taken separately, each vital phenomenon is not the result of some special force , but occurs according to the general laws of nature" At that time, bioorganic chemistry and biochemistry had not yet emerged as

independent directions, at first they were united physiological chemistry, but gradually they grew on the basis of all achievements into two independent sciences.

The science of bioorganic chemistry studies connection between the structure of organic substances and their biological functions, using mainly methods of organic, analytical, physical chemistry, as well as mathematics and physics

The main distinguishing feature of this subject is the study of the biological activity of substances in connection with the analysis of their chemical structure

Objects of study of bioorganic chemistry: biologically important natural biopolymers - proteins, nucleic acids, lipids, low molecular weight substances - vitamins, hormones, signal molecules, metabolites - substances involved in energy and plastic metabolism, synthetic drugs.

The main tasks of bioorganic chemistry include:

1. Development of methods for isolating and purifying natural compounds, using medical methods to assess the quality of a drug (for example, a hormone based on the degree of its activity);

2. Determination of the structure of a natural compound. All methods of chemistry are used: determination of molecular weight, hydrolysis, analysis of functional groups, optical research methods;

3. Development of methods for the synthesis of natural compounds;

4. Study of the dependence of biological action on structure;

5. Clarification of the nature of biological activity, molecular mechanisms of interaction with various cell structures or with its components.

The development of bioorganic chemistry over the decades is associated with the names of Russian scientists: D.I.Mendeleeva, A.M. Butlerov, N.N. Zinin, N.D. Zelinsky A.N. Belozersky N.A. Preobrazhensky M.M. Shemyakin, Yu.A. Ovchinnikova.

The founders of bioorganic chemistry abroad are scientists who have made many major discoveries: the structure of the secondary structure of proteins (L. Pauling), the complete synthesis of chlorophyll, vitamin B 12 (R. Woodward), the use of enzymes in the synthesis of complex organic substances. including gene (G. Koran) and others

In the Urals in Yekaterinburg in the field of bioorganic chemistry from 1928 to 1980. worked as the head of the department of organic chemistry of UPI, academician I.Ya. Postovsky, known as one of the founders in our country of the scientific direction of search and synthesis of drugs and the author of a number of drugs (sulfonamides, antitumor, anti-radiation, anti-tuberculosis). His research is continued by students who work under the leadership of academicians O.N. Chupakhin, V.N. Charushin at USTU-UPI and at the Institute of Organic Synthesis named after. AND I. Postovsky Russian Academy of Sciences.

Bioorganic chemistry is closely related to the tasks of medicine and is necessary for the study and understanding of biochemistry, pharmacology, pathophysiology, and hygiene. All the scientific language of bioorganic chemistry, the notation adopted and the methods used are no different from the organic chemistry you studied in school

Grodno" href="/text/category/grodno/" rel="bookmark">Grodno State Medical University", Candidate of Chemical Sciences, Associate Professor;

Associate Professor of the Department of General and Bioorganic Chemistry of the Educational Institution "Grodno State Medical University", Candidate of Biological Sciences, Associate Professor

Reviewers:

Department of General and Bioorganic Chemistry of the Educational Institution “Gomel State Medical University”;

– head Department of Bioorganic Chemistry Educational Institution "Belarusian State Medical University", Candidate of Medical Sciences, Associate Professor.

Department of General and Bioorganic Chemistry of the Educational Institution "Grodno State Medical University"

(minutes dated January 1, 2001)

Central Scientific and Methodological Council of the Educational Institution "Grodno State Medical University"

(minutes dated January 1, 2001)

Section in the specialty 1Medical and psychological affairs of the educational and methodological association of universities of the Republic of Belarus for medical education

(minutes dated January 1, 2001)

Responsible for release:

First Vice-Rector of the Educational Institution "Grodno State Medical University", Professor, Doctor of Medical Sciences

"Bioorganic chemistry"

Bioorganic chemistry is a fundamental natural science discipline. Bioorganic chemistry emerged as an independent science in the 2nd half of the 20th century at the intersection of organic chemistry and biochemistry. The relevance of the study of bioorganic chemistry is due to the practical problems facing medicine and agriculture (obtaining vitamins, hormones, antibiotics, plant growth stimulants, regulators of animal and insect behavior, and other medicines), the solution of which is impossible without using the theoretical and practical potential of bioorganic chemistry.

Bioorganic chemistry is constantly being enriched with new methods for the isolation and purification of natural compounds, methods for the synthesis of natural compounds and their analogues, knowledge about the relationship between the structure and biological activity of compounds, etc.

The latest approaches to medical education, related to overcoming the reproductive style in teaching, ensuring the cognitive and research activity of students, open up new prospects for realizing the potential of both the individual and the team.

The purpose and objectives of the academic discipline

Target: formation of a level of chemical competence in the medical education system, ensuring subsequent study of biomedical and clinical disciplines.

Tasks:

Students mastering the theoretical foundations of chemical transformations of organic molecules in relation to their structure and biological activity;

Formation: knowledge of the molecular foundations of life processes;

Development of skills to navigate the classification, structure and properties of organic compounds acting as medicines;

Formation of the logic of chemical thinking;

Development of skills to use qualitative analysis methods
organic compounds;

Chemical knowledge and skills, which form the basis of chemical competence, will contribute to the formation of the graduate’s professional competence.

Requirements for mastering an academic discipline

The requirements for the level of mastery of the content of the discipline “Bioorganic Chemistry” are determined by the educational standard of higher education of the first stage in the cycle of general professional and special disciplines, which is developed taking into account the requirements of the competency-based approach, which specifies the minimum content for the discipline in the form of generalized chemical knowledge and skills that constitute bioorganic competence university graduate:

a) generalized knowledge:

- understand the essence of the subject as a science and its connections with other disciplines;

Significance in understanding metabolic processes;

The concept of the unity of structure and reactivity of organic molecules;

Fundamental laws of chemistry necessary to explain the processes occurring in living organisms;

Chemical properties and biological significance of the main classes of organic compounds.

b) generalized skills:

Predict the reaction mechanism based on knowledge of the structure of organic molecules and methods of breaking chemical bonds;

Explain the significance of reactions for the functioning of living systems;

Use the acquired knowledge when studying biochemistry, pharmacology and other disciplines.

Structure and content of the academic discipline

In this program, the structure of the content of the discipline “bioorganic chemistry” consists of an introduction to the discipline and two sections that cover general issues of the reactivity of organic molecules, as well as the properties of hetero- and polyfunctional compounds involved in vital processes. Each section is divided into topics arranged in a sequence that ensures optimal learning and assimilation of the program material. For each topic, generalized knowledge and skills are presented that constitute the essence of students’ bioorganic competence. In accordance with the content of each topic, requirements for competencies are determined (in the form of a system of generalized knowledge and skills), for the formation and diagnosis of which tests can be developed.

Teaching methods

The main teaching methods that adequately meet the objectives of studying this discipline are:

Explanation and consultation;

Laboratory lesson;

Elements of problem-based learning (educational and research work of students);

Introduction to Bioorganic Chemistry

Bioorganic chemistry is a science that studies the structure of organic substances and their transformations in relation to biological functions. Objects of study of bioorganic chemistry. The role of bioorganic chemistry in the formation of a scientific basis for the perception of biological and medical knowledge at the modern molecular level.

The theory of the structure of organic compounds and its development at the present stage. Isomerism of organic compounds as the basis for the diversity of organic compounds. Types of isomerism of organic compounds.

Physicochemical methods for the isolation and study of organic compounds that are important for biomedical analysis.

Basic rules of IUPAC systematic nomenclature for organic compounds: substitutional and radical-functional nomenclature.

Spatial structure of organic molecules, its connection with the type of hybridization of the carbon atom (sp3-, sp2- and sp-hybridization). Stereochemical formulas. Configuration and conformation. Conformations of open chains (occluded, inhibited, canted). Energy characteristics of conformations. Newman's projection formulas. Spatial proximity of certain sections of the chain as a consequence of conformational equilibrium and as one of the reasons for the preferential formation of five- and six-membered cycles. Conformations of cyclic compounds (cyclohexane, tetrahydropyran). Energy characteristics of chair and bathtub conformations. Axial and equatorial connections. Relationship between spatial structure and biological activity.

Competency requirements:

· Know the objects of study and the main tasks of bioorganic chemistry,

· Be able to classify organic compounds according to the structure of the carbon skeleton and the nature of functional groups, use the rules of systematic chemical nomenclature.

· Know the main types of isomerism of organic compounds, be able to determine possible types of isomers using the structural formula of a compound.

· Know the different types of hybridization of carbon atomic orbitals, the spatial direction of atomic bonds, their type and number depending on the type of hybridization.

· Know the energy characteristics of the conformations of cyclic (chair, bathtub conformations) and acyclic (inhibited, oblique, eclipsed conformations) molecules, be able to depict them using Newman’s projection formulas.

· Know the types of stresses (torsional, angular, van der Waals) that arise in various molecules, their effect on the stability of the conformation and the molecule as a whole.

Section 1. The reactivity of organic molecules as a result of the mutual influence of atoms, mechanisms of organic reactions

Topic 1. Conjugated systems, aromaticity, electronic effects of substituents

Conjugated systems and aromaticity. Conjugation (p, p- and p, p-conjugation). Conjugated open-chain systems: 1,3-dienes (butadiene, isoprene), polyenes (carotenoids, vitamin A). Coupled closed-circuit systems. Aromaticity: criteria for aromaticity, Hückel's rule of aromaticity. Aromaticity of benzenoid (benzene, naphthalene, phenanthrene) compounds. Conjugation energy. Structure and reasons for the thermodynamic stability of carbo- and heterocyclic aromatic compounds. Aromaticity of heterocyclic (pyrrole, imidazole, pyridine, pyrimidine, purine) compounds. Pyrrole and pyridine nitrogen atoms, p-excessive and p-deficient aromatic systems.

Mutual influence of atoms and methods of its transmission in organic molecules. Delocalization of electrons as one of the factors increasing the stability of molecules and ions, its widespread occurrence in biologically important molecules (porphin, heme, hemoglobin, etc.). Polarization of connections. Electronic effects of substituents (inductive and mesomeric) as the cause of the uneven distribution of electron density and the emergence of reaction centers in the molecule. Inductive and mesomeric effects (positive and negative), their graphic designation in the structural formulas of organic compounds. Electron-donating and electron-withdrawing substituents.

Competency requirements:

· Know the types of conjugation and be able to determine the type of conjugation based on the structural formula of the compound.

· Know the criteria for aromaticity, be able to determine the aromatic compounds of carbo- and heterocyclic molecules using the structural formula.

· Be able to evaluate the electronic contribution of atoms to the creation of a single conjugated system, know the electronic structure of pyridine and pyrrole nitrogen atoms.

· Know the electronic effects of substituents, the reasons for their occurrence and be able to graphically depict their effect.

· Be able to classify substituents as electron-donating or electron-withdrawing based on the inductive and mesomeric effects they exhibit.

· Be able to predict the effect of substituents on the reactivity of molecules.

Topic 2. Reactivity of hydrocarbons. Radical substitution, electrophilic addition and substitution reactions

General patterns of reactivity of organic compounds as the chemical basis of their biological functioning. Chemical reaction as a process. Concepts: substrate, reagent, reaction center, transition state, reaction product, activation energy, reaction rate, mechanism.

Classification of organic reactions by result (addition, substitution, elimination, redox) and by mechanism - radical, ionic (electrophilic, nucleophilic), concerted. Types of reagents: radical, acidic, basic, electrophilic, nucleophilic. Homolytic and heterolytic cleavage of covalent bonds in organic compounds and the resulting particles: free radicals, carbocations and carbanions. Electronic and spatial structure of these particles and factors determining their relative stability.

Reactivity of hydrocarbons. Radical substitution reactions: homolytic reactions involving CH bonds of the sp3-hybridized carbon atom. The mechanism of radical substitution using the example of the halogenation reaction of alkanes and cycloalkanes. The concept of chain processes. The concept of regioselectivity.

Pathways for the formation of free radicals: photolysis, thermolysis, redox reactions.

Electrophilic addition reactions ( A.E.) in the series of unsaturated hydrocarbons: heterolytic reactions involving p-bonds between sp2-hybridized carbon atoms. Mechanism of hydration and hydrohalogenation reactions. Acid catalysis. Markovnikov's rule. Influence of static and dynamic factors on the regioselectivity of electrophilic addition reactions. Features of electrophilic addition reactions to diene hydrocarbons and small cycles (cyclopropane, cyclobutane).

Electrophilic substitution reactions ( S.E.): heterolytic reactions involving the p-electron cloud of the aromatic system. Mechanism of halogenation, nitration, alkylation reactions of aromatic compounds: p - and s- complexes. The role of the catalyst (Lewis acid) in the formation of an electrophilic particle.

The influence of substituents in the aromatic ring on the reactivity of compounds in electrophilic substitution reactions. Orienting influence of substituents (orientants of the first and second kind).

Competency requirements:

· Know the concepts of substrate, reagent, reaction center, reaction product, activation energy, reaction rate, reaction mechanism.

· Know the classification of reactions according to various criteria (by the final result, by the method of breaking bonds, by mechanism) and the types of reagents (radical, electrophilic, nucleophilic).

· Know the electronic and spatial structure of reagents and the factors determining their relative stability, be able to compare the relative stability of reagents of the same type.

· Know the methods of formation of free radicals and the mechanism of radical substitution reactions (SR) using examples of halogenation reactions of alkanes and cycloalakane.

· Be able to determine the statistical probability of the formation of possible products in radical substitution reactions and the possibility of regioselective occurrence of the process.

· Know the mechanism of electrophilic addition (AE) reactions in the reactions of halogenation, hydrohalogenation and hydration of alkenes, be able to qualitatively assess the reactivity of substrates based on the electronic effects of substituents.

· Know Markovnikov's rule and be able to determine the regioselectivity of the reactions of hydration and hydrohalogenation based on the influence of static and dynamic factors.

· Know the features of electrophilic addition reactions to conjugated diene hydrocarbons and small cycles (cyclopropane, cyclobutane).

· Know the mechanism of electrophilic substitution reactions (SE) in the reactions of halogenation, nitration, alkylation, acylation of aromatic compounds.

· Be able to determine, based on the electronic effects of substituents, their influence on the reactivity of the aromatic ring and their orienting effect.

Topic 3. Acid-base properties of organic compounds

Acidity and basicity of organic compounds: theories of Brønsted and Lewis. The stability of an acid anion is a qualitative indicator of acidic properties. General patterns in changes in acidic or basic properties in connection with the nature of the atoms in the acidic or basic center, the electronic effects of substituents at these centers. Acidic properties of organic compounds with hydrogen-containing functional groups (alcohols, phenols, thiols, carboxylic acids, amines, CH-acidity of molecules and cabric cations). p-bases and n- grounds. Basic properties of neutral molecules containing heteroatoms with lone pairs of electrons (alcohols, thiols, sulfides, amines) and anions (hydroxide, alkoxide ions, anions of organic acids). Acid-base properties of nitrogen-containing heterocycles (pyrrole, imidazole, pyridine). Hydrogen bonding as a specific manifestation of acid-base properties.

Comparative characteristics of the acidic properties of compounds containing a hydroxyl group (monohydric and polyhydric alcohols, phenols, carboxylic acids). Comparative characteristics of the basic properties of aliphatic and aromatic amines. Influence of the electronic nature of the substituent on the acid-base properties of organic molecules.

Competency requirements:

· Know the definitions of acids and bases according to Bronsted's protolytic theory and Lewis's electron theory.

· Know the Bronsted classification of acids and bases depending on the nature of the atoms of the acidic or basic centers.

· Know the factors influencing the strength of acids and the stability of their conjugate bases, be able to conduct a comparative assessment of the strength of acids based on the stability of their corresponding anions.

· Know the factors influencing the strength of Bronsted bases, be able to conduct a comparative assessment of the strength of the bases taking into account these factors.

· Know the reasons for the occurrence of a hydrogen bond, be able to interpret the formation of a hydrogen bond as a specific manifestation of the acid-base properties of a substance.

· Know the reasons for the occurrence of keto-enol tautomerism in organic molecules, be able to explain them from the perspective of the acid-base properties of compounds in connection with their biological activity.

· Know and be able to carry out qualitative reactions that allow you to distinguish polyhydric alcohols, phenols, thiols.

Topic 4. Nucleophilic substitution reactions at the tetragonal carbon atom and competitive elimination reactions

Nucleophilic substitution reactions at the sp3-hybridized carbon atom: heterolytic reactions caused by polarization of the carbon-heteroatom bond (halogen derivatives, alcohols). Groups that leave easily and difficultly: the connection between the ease of leaving a group and its structure. The influence of solvent, electronic and spatial factors on the reactivity of compounds in reactions of mono- and bimolecular nucleophilic substitution (SN1 and SN2). Stereochemistry of nucleophilic substitution reactions.

Hydrolysis reactions of halogen derivatives. Alkylation reactions of alcohols, phenols, thiols, sulfides, ammonia, amines. The role of acid catalysis in nucleophilic substitution of the hydroxyl group. Halogen derivatives, alcohols, esters of sulfuric and phosphoric acids as alkylating reagents. Biological role of alkylation reactions.

Mono- and bimolecular elimination reactions (E1 and E2): (dehydration, dehydrohalogenation). Increased CH acidity as a cause of elimination reactions accompanying nucleophilic substitution at the sp3-hybridized carbon atom.

Competency requirements:

· Know the factors that determine the nucleophilicity of reagents and the structure of the most important nucleophilic particles.

· Know the general laws of nucleophilic substitution reactions at a saturated carbon atom, the influence of static and dynamic factors on the reactivity of a substance in a nucleophilic substitution reaction.

· Know the mechanisms of mono- and bimolecular nucleophilic substitution, be able to evaluate the influence of steric factors, the influence of solvents, the influence of static and dynamic factors on the course of a reaction according to one of the mechanisms.

· Know the mechanisms of mono- and bimolecular elimination, the reasons for competition between nucleophilic substitution and elimination reactions.

· Know Zaitsev's rule and be able to determine the main product in the reactions of dehydration and dehydrohalogenation of unsymmetrical alcohols and haloalkanes.

Topic 5. Reactions of nucleophilic addition and substitution at the trigonal carbon atom

Nucleophilic addition reactions: heterolytic reactions involving the carbon-oxygen p-bond (aldehydes, ketones). The mechanism of reactions of interaction of carbonyl compounds with nucleophilic reagents (water, alcohols, thiols, amines). Influence of electronic and spatial factors, the role of acid catalysis, reversibility of nucleophilic addition reactions. Hemiacetals and acetals, their preparation and hydrolysis. Biological role of acetalization reactions. Aldol addition reactions. Basic catalysis. Structure of the enolate ion.

Nucleophilic substitution reactions in the series of carboxylic acids. Electronic and spatial structure of the carboxyl group. Nucleophilic substitution reactions at the sp2-hybridized carbon atom (carboxylic acids and their functional derivatives). Acylating agents (acid halides, anhydrides, carboxylic acids, esters, amides), comparative characteristics of their reactivity. Acylation reactions - the formation of anhydrides, esters, thioesters, amides - and their reverse hydrolysis reactions. Acetyl coenzyme A is a natural high-energy acylating agent. Biological role of acylation reactions. The concept of nucleophilic substitution at phosphorus atoms, phosphorylation reactions.

Oxidation and reduction reactions of organic compounds. Specificity of redox reactions of organic compounds. The concept of one-electron transfer, hydride ion transfer and the action of the NAD+ ↔ NADH system. Oxidation reactions of alcohols, phenols, sulfides, carbonyl compounds, amines, thiols. Reduction reactions of carbonyl compounds and disulfides. The role of redox reactions in life processes.

Competency requirements:

· Know the electronic and spatial structure of the carbonyl group, the influence of electronic and steric factors on the reactivity of the oxo group in aldehydes and ketones.

· Know the mechanism of reactions of nucleophilic addition of water, alcohols, amines, thiols to aldehydes and ketones, the role of a catalyst.

· Know the mechanism of aldol condensation reactions, the factors determining the participation of a compound in this reaction.

· Know the mechanism of reduction reactions of oxo compounds with metal hydrides.

· Know the reaction centers present in carboxylic acid molecules. Be able to conduct a comparative assessment of the strength of carboxylic acids depending on the structure of the radical.

· Know the electronic and spatial structure of the carboxyl group, be able to conduct a comparative assessment of the ability of the carbon atom of the oxo group in carboxylic acids and their functional derivatives (acid halides, anhydrides, esters, amides, salts) to undergo nucleophilic attack.

· Know the mechanism of nucleophilic substitution reactions using examples of acylation, esterification, hydrolysis of esters, anhydrides, acid halides, amides.

Topic 6. Lipids, classification, structure, properties

Lipids, saponifiable and unsaponifiable. Neutral lipids. Natural fats as a mixture of triacylglycerols. The main natural higher fatty acids that make up lipids: palmitic, stearic, oleic, linoleic, linolenic. Arachidonic acid. Features of unsaturated fatty acids, w-nomenclature.

Peroxide oxidation of unsaturated fatty acid fragments in cell membranes. The role of membrane lipid peroxidation in the effect of low doses of radiation on the body. Antioxidant protection systems.

Phospholipids. Phosphatidic acids. Phosphatidylcolamines and phosphatidylserines (cephalins), phosphatidylcholines (lecithins) are structural components of cell membranes. Lipid bilayer. Sphingolipids, ceramides, sphingomyelins. Brain glycolipids (cerebrosides, gangliosides).

Competency requirements:

· Know the classification of lipids and their structure.

· Know the structure of the structural components of saponified lipids - alcohols and higher fatty acids.

· Know the mechanism of reactions of formation and hydrolysis of simple and complex lipids.

· Know and be able to carry out qualitative reactions to unsaturated fatty acids and oils.

· Know the classification of unsaponifiable lipids, have an idea of ​​the principles of classification of terpenes and steroids, their biological role.

· Know the biological role of lipids, their main functions, have an idea of ​​the main stages of lipid peroxidation and the consequences of this process for the cell.

Section 2. Stereoisomerism of organic molecules. Poly- and heterofunctional compounds involved in vital processes

Topic 7. Stereoisomerism of organic molecules

Stereoisomerism in a series of compounds with a double bond (p-diastereomerism). Cis and trans isomerism of unsaturated compounds. E, Z – notation system for p-diastereomers. Comparative stability of p-diastereomers.

Chiral molecules. Asymmetric carbon atom as a center of chirality. Stereoisomerism of molecules with one center of chirality (enantiomerism). Optical activity. Fischer projection formulas. Glyceraldehyde as a configuration standard, absolute and relative configuration. D, L-system of stereochemical nomenclature. R, S-system of stereochemical nomenclature. Racemic mixtures and methods for their separation.

Stereoisomerism of molecules with two or more chiral centers. Enantiomers, diastereomers, mesoforms.

Competency requirements:

· Know the reasons for the occurrence of stereoisomerism in the series of alkenes and diene hydrocarbons.

· Be able to use the abbreviated structural formula of an unsaturated compound to determine the possibility of the existence of p-diastereomers, distinguish between cis - trans isomers, and evaluate their comparative stability.

· Know the elements of symmetry of molecules, the necessary conditions for the occurrence of chirality in an organic molecule.

· Know and be able to depict enantiomers using Fischer projection formulas, calculate the number of expected stereoisomers based on the number of chiral centers in a molecule, the principles of determining the absolute and relative configuration, the D-, L-system of stereochemical nomenclature.

· Know the methods for separating racemates, the basic principles of the R, S-system of stereochemical nomenclature.

Topic 8. Physiologically active poly- and heterofunctional compounds of the aliphatic, aromatic and heterocyclic series

Poly- and heterofunctionality as one of the characteristic features of organic compounds participating in vital processes and being the ancestors of the most important groups of drugs. Peculiarities in the mutual influence of functional groups depending on their relative location.

Polyhydric alcohols: ethylene glycol, glycerin. Esters of polyhydric alcohols with inorganic acids (nitroglycerin, glycerol phosphates). Diatomic phenols: hydroquinone. Oxidation of diatomic phenols. Hydroquinone-quinone system. Phenols as antioxidants (free radical scavengers). Tocopherols.

Dibasic carboxylic acids: oxalic, malonic, succinic, glutaric, fumaric. The conversion of succinic acid to fumaric acid is an example of a biologically important dehydrogenation reaction. Decarboxylation reactions, their biological role.

Amino alcohols: aminoethanol (colamine), choline, acetylcholine. The role of acetylcholine in the chemical transmission of nerve impulses at synapses. Aminophenols: dopamine, norepinephrine, adrenaline. The concept of the biological role of these compounds and their derivatives. Neurotoxic effects of 6-hydroxydopamine and amphetamines.

Hydroxy and amino acids. Cyclization reactions: the influence of various factors on the process of cycle formation (implementation of the corresponding conformations, size of the resulting cycle, entropy factor). Lactones. Lactams. Hydrolysis of lactones and lactams. Elimination reaction of b-hydroxy and amino acids.

Aldehyde and keto acids: pyruvic, acetoacetic, oxaloacetic, a-ketoglutaric. Acid properties and reactivity. Reactions of decarboxylation of b-keto acids and oxidative decarboxylation of a-keto acids. Acetoacetic ester, keto-enol tautomerism. Representatives of “ketone bodies” are b-hydroxybutyric, b-ketobutyric acids, acetone, their biological and diagnostic significance.

Heterofunctional benzene derivatives as medicines. Salicylic acid and its derivatives (acetylsalicylic acid).

Para-aminobenzoic acid and its derivatives (anesthesin, novocaine). Biological role of p-aminobenzoic acid. Sulfanilic acid and its amide (streptocide).

Heterocycles with several heteroatoms. Pyrazole, imidazole, pyrimidine, purine. Pyrazolone-5 is the basis of non-narcotic analgesics. Barbituric acid and its derivatives. Hydroxypurines (hypoxanthine, xanthine, uric acid), their biological role. Heterocycles with one heteroatom. Pyrrole, indole, pyridine. Biologically important pyridine derivatives are nicotinamide, pyridoxal, and isonicotinic acid derivatives. Nicotinamide is a structural component of the coenzyme NAD+, which determines its participation in OVR.

Competency requirements:

· Be able to classify heterofunctional compounds by composition and by their relative arrangement.

· Know the specific reactions of amino and hydroxy acids with a, b, g - arrangement of functional groups.

· Know the reactions leading to the formation of biologically active compounds: choline, acetylcholine, adrenaline.

· Know the role of keto-enol tautomerism in the manifestation of the biological activity of keto acids (pyruvic acid, oxaloacetic acid, acetoacetic acid) and heterocyclic compounds (pyrazole, barbituric acid, purine).

· Know the methods of redox transformations of organic compounds, the biological role of redox reactions in the manifestation of the biological activity of diatomic phenols, nicotinamide, and the formation of ketone bodies.

Subject9 . Carbohydrates, classification, structure, properties, biological role

Carbohydrates, their classification in relation to hydrolysis. Classification of monosaccharides. Aldoses, ketoses: trioses, tetroses, pentoses, hexoses. Stereoisomerism of monosaccharides. D- and L-series of stereochemical nomenclature. Open and cyclic forms. Fisher's formulas and Haworth's formulas. Furanoses and pyranoses, a- and b-anomers. Cyclo-oxo-tautomerism. Conformations of pyranose forms of monosaccharides. The structure of the most important representatives of pentoses (ribose, xylose); hexoses (glucose, mannose, galactose, fructose); deoxysugars (2-deoxyribose); amino sugars (glucosamine, mannosamine, galactosamine).

Chemical properties of monosaccharides. Nucleophilic substitution reactions involving an anomeric center. O - and N-glycosides. Hydrolysis of glycosides. Phosphates of monosaccharides. Oxidation and reduction of monosaccharides. Reducing properties of aldoses. Glyconic, glycaric, glycuronic acids.

Oligosaccharides. Disaccharides: maltose, cellobiose, lactose, sucrose. Structure, cyclo-oxo-tautomerism. Hydrolysis.

Polysaccharides. General characteristics and classification of polysaccharides. Homo- and heteropolysaccharides. Homopolysaccharides: starch, glycogen, dextrans, cellulose. Primary structure, hydrolysis. The concept of secondary structure (starch, cellulose).

Competency requirements:

· Know the classification of monosaccharides (according to the number of carbon atoms, the composition of functional groups), the structure of open and cyclic forms (furanose, pyranose) of the most important monosaccharides, their ratio of D - and L - series of stereochemical nomenclature, be able to determine the number of possible diastereomers, classify stereoisomers as diastereomers , epimers, anomers.

· Know the mechanism of cyclization reactions of monosaccharides, the reasons for the mutarotation of monosaccharide solutions.

· Know the chemical properties of monosaccharides: redox reactions, reactions of formation and hydrolysis of O - and N-glycosides, esterification reactions, phosphorylation.

· Be able to carry out high-quality reactions on the diol fragment and the presence of reducing properties of monosaccharides.

· Know the classification of disaccharides and their structure, the configuration of the anomeric carbon atom forming a glycosidic bond, tautomeric transformations of disaccharides, their chemical properties, biological role.

· Know the classification of polysaccharides (in relation to hydrolysis, according to monosaccharide composition), the structure of the most important representatives of homopolysaccharides, the configuration of the anomeric carbon atom forming a glycosidic bond, their physical and chemical properties, and biological role. Have an idea of ​​the biological role of heteropolysaccharides.

Topic 10.a-Amino acids, peptides, proteins. Structure, properties, biological role

Structure, nomenclature, classification of a-amino acids that make up proteins and peptides. Stereoisomerism of a-amino acids.

Biosynthetic pathways for the formation of a-amino acids from oxoacids: reductive amination reactions and transamination reactions. Essential amino acids.

Chemical properties of a-amino acids as heterofunctional compounds. Acid-base properties of a-amino acids. Isoelectric point, methods for separating a-amino acids. Formation of intracomplex salts. Reactions of esterification, acylation, alkylation. Interaction with nitrous acid and formaldehyde, the significance of these reactions for the analysis of amino acids.

g-Aminobutyric acid is an inhibitory neurotransmitter of the central nervous system. Antidepressant effect of L-tryptophan, serotonin - as a sleep neurotransmitter. Mediator properties of glycine, histamine, aspartic and glutamic acids.

Biologically important reactions of a-amino acids. Deamination and hydroxylation reactions. Decarboxylation of a-amino acids is the path to the formation of biogenic amines and bioregulators (colamine, histamine, tryptamine, serotonin.) Peptides. Electronic structure of the peptide bond. Acid and alkaline hydrolysis of peptides. Establishment of amino acid composition using modern physicochemical methods (Sanger and Edman methods). Concept of neuropeptides.

Primary structure of proteins. Partial and complete hydrolysis. The concept of secondary, tertiary and quaternary structures.

Competency requirements:

· Know the structure, stereochemical classification of a-amino acids, belonging to the D- and L-stereochemical series of natural amino acids, essential amino acids.

· Know the ways of synthesis of a-amino acids in vivo and in vitro, know the acid-base properties and methods of converting a-amino acids into an isoelectric state.

· Know the chemical properties of a-amino acids (reactions on amino and carboxyl groups), be able to carry out qualitative reactions (xantoprotein, with Cu(OH)2, ninhydrin).

· Know the electronic structure of the peptide bond, the primary, secondary, tertiary and quaternary structure of proteins and peptides, know how to determine the amino acid composition and amino acid sequence (Sanger method, Edman method), be able to carry out the biuret reaction for peptides and proteins.

· Know the principle of the method of peptide synthesis using protection and activation of functional groups.

Topic 11. Nucleotides and nucleic acids

Nucleic bases that make up nucleic acids. Pyrimidine (uracil, thymine, cytosine) and purine (adenine, guanine) bases, their aromaticity, tautomeric transformations.

Nucleosides, reactions of their formation. The nature of the connection between the nucleic base and the carbohydrate residue; configuration of the glycosidic center. Hydrolysis of nucleosides.

Nucleotides. The structure of mononucleotides that form nucleic acids. Nomenclature. Hydrolysis of nucleotides.

Primary structure of nucleic acids. Phosphodiester bond. Ribonucleic and deoxyribonucleic acids. Nucleotide composition of RNA and DNA. Hydrolysis of nucleic acids.

The concept of the secondary structure of DNA. The role of hydrogen bonds in the formation of secondary structure. Complementarity of nucleic bases.

Medicines based on modified nucleic bases (5-fluorouracil, 6-mercaptopurine). The principle of chemical similarity. Changes in the structure of nucleic acids under the influence of chemicals and radiation. Mutagenic effect of nitrous acid.

Nucleoside polyphosphates (ADP, ATP), features of their structure that allow them to perform the functions of high-energy compounds and intracellular bioregulators. The structure of cAMP, the intracellular “messenger” of hormones.

Competency requirements:

· Know the structure of pyrimidine and purine nitrogenous bases, their tautomeric transformations.

· Know the mechanism of reactions for the formation of N-glycosides (nucleosides) and their hydrolysis, the nomenclature of nucleosides.

· Know the fundamental similarities and differences between natural and synthetic antibiotic nucleosides in comparison with the nucleosides that make up DNA and RNA.

· Know the reactions of nucleotide formation, the structure of mononucleotides that make up nucleic acids, their nomenclature.

· Know the structure of cyclo- and polyphosphates of nucleosides, their biological role.

· Know the nucleotide composition of DNA and RNA, the role of the phosphodiester bond in creating the primary structure of nucleic acids.

· Know the role of hydrogen bonds in the formation of the secondary structure of DNA, the complementarity of nitrogenous bases, the role of complementary interactions in the implementation of the biological function of DNA.

· Know the factors that cause mutations and the principle of their action.

Main:

1. Romanovsky, bioorganic chemistry: a textbook in 2 parts /. - Minsk: BSMU, 20с.

2. Romanovsky, to the workshop on bioorganic chemistry: textbook / edited. – Minsk: BSMU, 1999. – 132 p.

3. Tyukavkina, N. A., Bioorganic chemistry: textbook / , . – Moscow: Medicine, 1991. – 528 p.

Additional:

4. Ovchinnikov, chemistry: monograph /.

– Moscow: Education, 1987. – 815 p.

5. Potapov: textbook /. - Moscow:

Chemistry, 1988. – 464 p.

6. Riles, A. Fundamentals of organic chemistry: a textbook / A. Rice, K. Smith,

R. Ward. – Moscow: Mir, 1989. – 352 p.

7. Taylor, G. Fundamentals of organic chemistry: textbook / G. Taylor. -

Moscow: Mirs.

8. Terney, A. Modern organic chemistry: a textbook in 2 volumes /

A. Terney. – Moscow: Mir, 1981. – 1310 p.

9. Tyukavkina, for laboratory classes on bioorganic

chemistry: textbook / [etc.]; edited by N.A.

Tyukavkina. – Moscow: Medicine, 1985. – 256 p.

10. Tyukavkina, N. A., Bioorganic chemistry: A textbook for students

medical institutes / , . - Moscow.

Bioorganic chemistry studies the structure and properties of substances involved in life processes in connection with the knowledge of their biological

The set of chemical reactions occurring in the body is called metabolism, or metabolism. Substances produced in cells

Metabolism

Basic principles of the theory of the structure of organic compounds A.M. Butlerov

H o m o l o g h i c e r i d

Classification of organic compounds according to the structure of the carbon skeleton

Classification of organic compounds according to the presence of functional groups

Nomenclature of organic compounds

Isomerism of organic compounds

This is geometric isomerism

Plane polarized light

Biological activity of enantiomers

Acidity and basicity of organic compounds

Types of acids and bases according to Brønsted

The main centers in the novocaine molecule

Use of basic properties to obtain water-soluble forms of drugs

Acid-base properties of substances and their entry into the body

Types of reactions in organic chemistry

Depending on the electronic nature of the reagents, reactions are distinguished: nucleophilic, electrophilic and free radical

Classification of reactions according to particular characteristics

Selectivity of reactions in organic chemistry

Properties of poly- and heterofunctional compounds