MEDICAL CHEMISTRY Examination topics 2007
general
medicine
Some names of compounds are
marked by an asterisk (*). It denotes that the complete presentation of the
structural formula is not required. Nevertheless, the structural formula should
be recognized as well as the proper names given to the important substructures.
1
Basic chemical terms: expression of amounts of substances, molar quantities.
2
Intermolecular forces, the resulting properties of matter. Similia
similibus solvuntur – typical examples, the biological significance.
3
Energetics of chemical reactions: enthalpy, entropy, and Gibbs free
energy changes, their relationship. The driving force of chemical reactions.
4
High-energy compounds, structures, energetic coupling of reactions, the
biological significance.
5
Reaction rate. Kinetic equations, progress curves for the 1st
order and the 0th order reactions, catalysts.
6
Chemical equilibrium, the equilibrium constant, the relationship
between K and DG°. Factors influencing
equilibrium.
7
Liquid dispersions, types and fundamental properties, expressing of
concentration.
8
Colligative properties of solutions, osmotic pressure, osmolarity,
isotonic solutions, the osmolality of blood plasma.
9
Liquid colloidal dispersions (hydrophilic colloidal solutions -
molecular and micellar). Factors stabilizing and destabilizing liquid colloidal
dispersions (ionic strength, electric charge, solvation shell, surfactants).
10 Adsorption, application of
polar and non-polar adsorbents, adsorption chromatography.
11 Surfactants - structural
types, formation of micelles, solubilizing and emulsifying effects.
12 Weak electrolytes, the
ionization constant K and percent
ionization ac. Strong electrolytes,
concentration versus activity of ions, ionic strength.
13 Acids and bases, conjugate
pairs, weak acids and bases, pKA and pKB. The pH values of aqueous
solutions of strong and weak acids and bases.
14 Titration curves,
differences between titration curves of strong and weak acids.
15 Hydrolysis of ions.
16 Buffer solutions, the action
of buffers. The relation between the buffer composition and pH value, buffer
capacity, its relation to the titration curve.
17 Buffer systems in the human
body.
18 Precipitation, solubility
product constant KS,
soluble and insoluble carbonates and phosphates.
19 Coordination compounds (structure,
stability, examples and nomenclature), chelation.
20 Oxidation and reduction,
oxidizing and reducing agents, electrode potential of the half-cell E° and E. Decisions about the direction of a redox reaction considering
the DE. The relationship between DE and DG.
21 Redox pairs of biological
significance (substrates, coenzymes of dehydrogenases, ascorbic acid).
22 Elements in the human body
(essential macroelements and microelements).
23 English chemical
nomenclature of inorganic compounds; Latin nomenclature of pharmaceuticals
(oxides, hydroxides, inorganic and organic acids and salts).
24 Oxygen, composition of air,
ozone, reactive oxygen species, hydrogen peroxide, water.
25 Halogens, biological
significance of halides, blood plasma chloride.
26 Sulfur compounds, selenium -
biological significance.
27 Nitrogen, inorganic nitrogen
compounds in nature (the nitrogen cycle), biological importance.
28 Phosphorus as biogenic
element (phosphates, diphosphates, phosphate esters important in metabolism).
29 Biological significance of
carbon compounds (oxides, carbonates, cyanides), nutrients, carbon cycle in the
nature.
30 Si, B, Al - compounds
applicable in medicine (antacids, boric acid and borax).
31 Magnesium, alkaline earth
metals, biological role of Ca2+ and Mg2+ ions,
significant compounds, water containing Ca+Mg ions, insoluble calcium
compounds.
32 Na, K – human intake of
these minerals, biological role of Na+ and K+ ions, blood
plasma concentration, significant sodium and potassium compounds.
33 Fe - biochemical
significance, forms of iron occurrence in the body, some important iron
compounds.
34 Toxic inorganic compounds
(ozone, SO2, nitrites, HCN,
CO, As, Pb, Ba, Cd, Hg, asbestos).
35 Constitution of organic
compounds, structural isomerism (examples). Tautomerism (types, examples).
Conformation of alkanes and cycloalkanes (cyclohexane, decalin, sterane).
36 Stereoisomerism (cis-trans isomerism, optical isomerism).
Notation of chiral molecules configuration (Fischer projection formulas, R/S
convention), enantiomers, racemates, diastereomers.
37 Important and useful arenes
(benzene, toluene, styrene), biotransformation of arenes, polycyclic aromatic
hydrocarbons.
38 Alcohols - types, general
properties, reactions, ethanol and methanol.
39 Polyhydric alcohols
(glycols, glycerol, alditols, inositol), enols.
40 Phenols, general properties.
Quinones (*ubiquinone, 1,4-naphthoquinone). Ethers.
41 Esters of inorganic acids,
biological significance (nitrates, sulfates, phosphates, organophosphates).
42 Organic compounds of sulfur
(thiols, alkyl sulfides, sulfonic acids).
43 Reactions of carbonyl
compounds, biologically important aldehydes and ketones (acetone, pyridoxal,
malondialdehyde, allysine, *retinal, the biochemical term "ketone
bodies").
44 Carboxylic acids - general
properties. The most important saturated and unsaturated aliphatic and aromatic
acids (mono- and dicarboxylic), the trivial and systematic names of those
acids, ibuprofen.
45 Carboxylic acid derivatives
(acid anhydrides, mixed anhydrides, esters, thioesters, amides).
46 Derivatives of carbonic acid
(carbamates, urea, guanidine, creatine, phosphocreatine, creatinine, arginine).
47 Aliphatic and aromatic
hydroxy acids (structures and names, products of oxidation, lactones).
48 Oxo carboxylic acids of
biochemical importance, the term ”ketone bodies“.
49 p-Aminobenzoic
acid, the relation of PABA to folic acid. The principle of sulfonamides action.
50 Biochemically significant
interconversions of some aliphatic mono- and dicarboxylic acids (saturated acids to unsaturated and
to hydroxy carboxylic and oxo carboxylic acids, transamination of amino acids).
51 Amines - general properties,
basicity, reaction with aldehydes and ketones, origins of amides, oxidative
deamination of amines.
52 Biogenic amines,
catecholamines, phenethylamines.
53 Quaternary ammonium salts
exhibiting biological significance (choline, *myorelaxants, carnitine, cationic
surfactants).
54 Halogenated organic
compounds (solvents, PCBs, chlorofluorocarbons, herbicides, dioxins),
halogenated anesthetics. Nitro compounds.
55 Derivatives of pyrrole,
pyrrolidine, indole (porphin, *porphyrins, haem, *corrin, proline, tryptophan
and derivatives of it).
56 Imidazole, thiazole, and
their derivatives (histidine and histamine, *biotin, *thiamine, the *skeleton of penicillins).
57 Derivatives of pyridine and
chroman (pyridoxal phosphate, nicotinic acid, nicotinamide, *tocopherol,
*coumarin).
58 Pyrimidine derivatives
(bases in nucleosides, *thiamine, cytostatic analogs of pyrimidine bases).
59 Purine and its derivatives
(purine bases, uric acid, allopurinol, methylxanthines).
60 Pteridine, isoalloxazine and
derivatives (*biopterin, *folic acid, *riboflavin).
61 General characteristic of alkaloids. Examples of important alkaloids.
62 Toxic organic chemicals.
63 Monosaccharides -
definition, chirality in monosaccharides (expressing the
configuration
by Fischer projection), epimers, trivial names and the configurations of
the most important monosaccharides.
64 Cyclic forms of
monosaccharides (anomers, Haworth projection
formulas, conformation formulas of pyranoses).
65 Reactions of monosaccharides
(tests for reducing properties, products of oxidation and/or reduction of
monosaccharides). Alditols and acids derived from monosaccharides (general
structures, group names, significance - esp. of glucuronic acid and of
*neuraminic acid).
66 Formation of glycosidic bonds,
glycoside types (O-, N-, and ester glycosidic bonds).
67 Amino sugars (general
structure, nomenclature, N-acetylation, importance for heteropolysaccharides,
*neuraminic acid and *sialic acids) and deoxy sugars (general structure, D-deoxyribose as a constituent of nucleosides).
68 Disaccharides (reducing, non-reducing,
structures, properties).
69 Homopolysaccharides (starch,
glycogen, cellulose, inulin, dietary fibre).
70 Heteropolysaccharides
(constituents, common types of *glycosaminoglycans).
71 Nucleosides - structures,
nomenclature.
72 Nucleotides - structural
types (nucleoside triphosphates, cAMP, NAD+, FAD, coenzyme A).
73 Characterization of
deoxyribonucleic acid structure (polarity of strands and bonds, B-form of the
DNA double-helix, base pairing, denaturation and hybridization).
74 Main classes of RNA
molecules, characteristics of the structures and of the functions (stems and
loops, description of the *tRNA).
75 Fatty acids (saturated,
unsaturated, essential acids). Eicosanoids.
76 Triacylglycerols,
properties, structure, products of hydrolysis, fats and oils in the nutrition.
77 Glycerophospholipids,
structural classes, differences in polarity, significance.
78 Sphingophospholipids,
glycolipids (neutral and acidic types, components, group names).
79 Terpenes, major classes with
examples (*menthane, *phytol, squalene, *carotenes).
80 Steroids, the basic
structure, numbering of carbon atoms, stereochemistry; cholesterol, bile acids,
significance.
81 Steroid hormones:
corticosteroids (cortisol, aldosterone), gestagens, androgens, estrogens
(structural differences, sites of secretion, notion about their functions).
82 Twenty standard amino acids,
classification based on chemical structure and polarity of a side chain.
83 Standard amino acids,
ionization and the pH value, isoelectric point.
84 Peptides, groups of peptides
possessing biological activity (glutathione, examples of hormones, antibiotics,
toxins).
85 Proteins, qualitative
differences between peptides and proteins, levels for characterization of the
structures, three main classes of proteins (globular, fibrous, and membrane
proteins).
86 Primary and secondary
structures of proteins (definition of the terms, types of bonds).
87 Tertiary and quaternary
structures of proteins (definition, stabilizing bonds, super-secondary motifs
and domains, stability versus flexibility of the native protein conformations,
protein denaturation).
88 Properties of proteins -
solubility, ionization, salting out, denaturation, precipitation.
89 Glycoproteins – types of
structures, significance, different types of glycosidic linkages to proteins in
glycoproteins.
90 Hydrophilic vitamins.
91 Lipophilic vitamins.
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