ORGANIC CHEMISTRY FOR MEDICINE
CONTENTS 1 ORGANIC CHEMISTRY IN MEDICINE……………………………… HISTORY……………………………………………………………… 1 1 CHARACTERISTICS OF CARBON……………………………………… 1 2 STRUCTURAL THEORY……………………………………………… STRUCTURAL DRAWINGS………………………………………… 1 3 FUNCTIONAL GROUPS……………………………………………… 1 4 NOMENCLATURE OF ORGANIC COMPOUNDS………………………… 1 5 CLASSIFICATION OF ORGANIC COMPOUNDS………………………… ALIPHATIC COMPOUNDS……………………………………… AROMATIC COMPOUNDS……………………………………… HETEROCYCLIC COMPOUNDS…………………………………… POLYMERS…………………………………………………… BIOMOLECULES……………………………………………… 1 6 MEDICAL SIGNIFICANCE…………………………………………… SUMMARY…………………………………………………………… BIBLIOGRAPHY………………………………………………………… REVIEW TEST………………………………………………………… 2 REACTIONS AND EFFECTS IN ORGANIC CHEMISTRY……………… 2 1 NOMENCLATURE AND CLASSIFICATION……………………………… 2 2 REACTIONS IN ORGANIC CHEMISTRY AND THEIR MEDICAL SIGNIFICANCE…………………………………………………… SUBSTITUTION REACTIONS…………………………………… ELECTROPHILIC SUBSTITUTION……………………………… NUCLEOPHILIC SUBSTITUTION……………………………… RADICAL SUBSTITUTION…………………………………… ADDITION REACTIONS………………………………………… ELECTROPHILIC ADDITION………………………… ……… NUCLEOPHILIC ADDITION………………………………… RADICAL ADDITION……………………………………… ELIMINATION REACTIONS……………………………………… REDOX REACTIONS…………………………………………… REARRANGEMENT REACTIONS………………………………… POLYMERIZATION…………………………………………… POLYCONDENSATION AND BIOPOLYCONDENSATES…………… 2 3 EFFECTS IN ORGANIC CHEMISTRY AND THEIR MEDICAL SIGNIFICANCE INDUCTIVE EFFECT…………………………………………… INFLUENCE OF THE INDUCTIVE EFFECT ON THE PROPERTIES OF ORGANIC COMPOUNDS…………………………………… ACIDITY AND BASICITY…………………………………… MESOMERIC EFFECT………………………………………… MESOMERISM IN CONJUGATED MOLECULES………………… 3 ISOMERISM…………………………………………………… 3 1 NOMENCLATURE AND CLASSIFICATION………………………………… 3 2 CONSTITUTIONAL ISOMERISM AND ITS MEDICAL SIGNIFICANCE……… CHAIN ISOMERISM…………………………………………… POSITION ISOMERISM……………………………………… METAMERISM……………………………………………… TAUTOMERISM……………………………………………… 3 3 STEREOISOMERISM AND ITS MEDICAL SIGNIFICANCE………………… DIASTEREOMERISM…………………………………………… CIS-TRANS ISOMERISM…………………………………… Z-E ISOMERISM……………………………………… CONFORMERISM………………………………………… ENANTIOMERISM…………………………………………… D,L-FISCHER'S NOMENCLATURE…………………………… R,S-SYSTEM OF CAHN, INGOLD, AND PRELOG………………… 3 4 FUNCTIONAL GROUP ISOMERISM AND ITS MEDICAL SIGNIFICANCE…… 4 HYDROCARBONS………………………………………………… 4 1 NOMENCLATURE AND CLASSIFICATION……………………………… 4 2 ALKANES………………………………………………………… PHYSICAL PROPERTIES……………………………………… CHEMICAL PROPERTIES……………………………………… ISOMERISM……………………………………………… OXIDATION……………………………………………… HALOGENATION………………………………………… CYCLIZATION…………………………………………… SUBSTITUTION…………………………………………… CRACKING……………………………………………… COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE……………… METHANE AND ETHANE…………………………………… CYCLOALKANES…………………………………………… CYCLOHEXANE……………………………………… 4 3 ALKENES………………………………………………………… ADDITION REACTIONS…………………………………… HYDROGENATION………………………………………… BROMINATION…………………………………………… HYDROHALOGENATION…………………………………… HYDRATION……………………………………………… NITRILATION……………………………………………… POLYMERIZATION………………………………………… ETHYLENE……………………………………………… 4 4 ALKYNES……………………………………………………… KUCHEROV REACTION…………………………………… ACETYLENE……………………………………………… 5 HALOALKANES………………………………………………… 5 1 NOMENCLATURE AND CLASSIFICATION…………………………… 5 2 OCCURRENCE…………………………………………………… FROM ALKANES…………………………………………… FROM ALKENES AND ALKYNES……………………………… FROM ALCOHOLS…………………………………………… FROM CARBOXYLIC ACIDS…………………………………… BIOSYNTHESIS……………………………………………… 5 3 PHYSICAL PROPERTIES………………………………………… 5 4 CHEMICAL PROPERTIES………………………………………… SUBSTITUTION……………………………………………… ELIMINATION……………………………………………… 5 5 COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE…………………… ALKYL FLUORIDES…………………………………………… ALKYL CHLORIDES…………………………………………… ALKYL BROMIDES…………………………………………… ALKYL IODIDES……………………………………………… CHLOROFLUOROCARBONS……………………………………… 6 AROMATIC COMPOUNDS……………………………………… 6 1 NOMENCLATURE AND CLASSIFICATION…………………………… 6 2 BENZENE AND ITS MEDICAL SIGNIFICANCE……………………… CHEMICAL (AROMATIC) PROPERTIES………………………… PRIMARY SUBSTITUTES OF FIRST TYPE…………………… PRIMARY SUBSTITUTES OF SECOND TYPE………………… NUCLEOPHILIC SUBSTITUTION…………………………… COUPLING REACTIONS…………………………………… 6 3 BENZENE DERIVATIVES AND THEIR MEDICAL SIGNIFICANCE………… ALKYLBENZENES……………………………………………… SATURATED ALKYLBENZENES……………………………… UNSATURATED ALKYLBENZENES…………………………… SUBSTITUTED ALKYLBENZENES………………………………… AROMATIC HALOGENS…………………………………… 6 4 CYCLOHEPTATRIENE……………………………………………… 6 5 CONDENSED AROMATIC HYDROCARBONS AND THEIR MEDICAL SIGNIFICANCE…………………………………………………… CARCINOGENS……………………………………………… 7 ALCOHOLS, THIOLS, AND PHENOLS………………………… …… 7 1 ALCOHOLS……………………………………………………… HISTORY…………………………………………………………… NOMENCLATURE AND CLASSIFICATION…………………………… OCCURRENCE…………………………………………………… ZIEGLER AND OXO PROCESSES……………………………… HYDRATION REACTIONS……………………………………… BIOLOGICAL ROUTES……………………………………… PHYSICAL PROPERTIES………………………………………… CHEMICAL PROPERTIES………………………………………… DEPROTONATION…………………………………………… DEHYDRATION…………………………………………… REACTIONS WITH BASES AND ACIDS………………………… ESTERIFICATION…………………………………………… OXIDATION………………………………………………… DEHYDRATION……………………………………………… COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE………………… METHANOL………………………………………………… ETHANOL………………………………………………… ETHYLENE GLYCOL………………………………………… GLYCEROL………………………………………………… POLYVALENT ALCOHOLS……………………………………… CYCLIC ALCOHOLS………………………………………… ALKANOLAMINES…………………………………………… ETHANOLAMINE……………………………………… SPHINGOSINE………………………………………… 7 2 THIOLS……………………………………………………… OCCURRENCE………………………………………………… ACIDITY…………………………………………………… 2-MERCAPTOETHANOL AND 1,4-DITHIOTHREITOL………………… THIOESTERS……………………………………………… 7 3 PHENOLS……………………………………………………… DIVALENT AND TRIVALENT PHENOLS……………………… … CRESOLS…………………………………………………… EPINEPHRINE……………………………………………… PARACETAMOL……………………………………………… BIBLIOGRAPHY……………………………………………………… 8 ETHERS……………………………………………………… 8 1 NOMENCLATURE AND CLASSIFICATION…………………………… 8 2 OCCURRENCE…………………………………………………… DEHYDRATION OF ALCOHOLS………………………………… WILLIAMSON ETHER SYNTHESIS……………………………… ULLMANN CONDENSATION………………………………… ELECTROPHILIC ADDITION OF ALCOHOLS TO ALKENES…………… 8 3 CHEMICAL PROPERTIES………………………………………… LEWIS BASES……………………………………………… PEROXIDE FORMATION……………………………………… 8 4 COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE………………… DIETHYL ETHER…………………………………………… POLYETHERS……………………………………………… SUMMARY………………………………………………………… BIBLIOGRAPHY…………………………………………………… … 9 QUINONES…………………………………………………… 9 1 NOMENCLATURE AND CLASSIFICATION…………………………… 9 2 PHYSICAL AND CHEMICAL PROPERTIES………………………… 9 3 COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE………………… BIBLIOGRAPHY………………………………………………… …… 10 CARBONYL COMPOUNDS ALDEHYDES AND KETONES………… HISTORY…………………………………………………………………… 10 1 CARBONYL GROUP……………………………………………… 10 2 ALDEHYDES……………………………………………… …… NOMENCLATURE AND CLASSIFICATION……………………… CHEMICAL PROPERTIES…………………………………… OXIDATION…………………………………………… REDUCTION…………………………………………… NUCLEOPHILIC ADDITION REACTIONS……………………… FORMATION OF HEMIACETALS………………………… ACIDITY OF THE HYDROGEN ATOM AT THE ?-C ATOM……… POLYMERIZATION……………………………………… ENOLIZATION………………………………………… COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE…………… FORMALDEHYDE……………………………………… ACETALDEHYDE………………………………………… CHLORAL……………………………………………… BENZALDEHYDE……………………………………… AMYGDALIN…………………………………………… VANILLIN……………………………………………… ACROLEIN……………………………………………… DIALDEHYDES………………………………………… 10 3 KETONES…………………………………………………… … FORMATION OF HEMIKETALS…………………………… ADDITION OF HYDROGEN CYANIDE……………………… KETO-ENOL TAUTOMERIZATION…………………………… ACID/BASE PROPERTIES OF KETONES……………………… ACETONE……………………………………………… ACETOPHENONE………………………………………… DIKETONES…………………………………………… UNSATURATED KETONES………………………………… CYCLIC KETONES……………………………………… REVIEW TEST……………………………………………………… 11 CARBOXYLIC ACIDS…………………………………………… 11 1 CARBOXYL GROUP……………………………………………… 11 2 MONOCARBOXYLIC ACIDS……………………………………… ACIDITY……………………………………………… NUCLEOPHILIC SUBSTITUTION IN THE CARBOXYL GROUP…… INTERACTION WITH METALS, BASES, AND BASIC OXIDES…… ESTERIFICATION………………………………………… CLAISEN CONDENSATION……………………………… HYDROCARBON RESIDUE REACTIONS…………………… ALIPHATIC MONOCARBOXYLIC ACIDS AND THEIR MEDICAL SIGNIFICANCE……………………………………………… SATURATED ACIDS……………………………………… FORMIC ACID……………………………………… ACETIC ACID……………………………………… PROPIONIC ACID…………………………………… BUTYRIC ACID……………………………………… VALERIC ACID……………………………………… PALMITIC ACID…………………………………… STEARIC ACID……………………………………… UNSATURATED ACIDS…………………………………… ACRYLIC ACID……………………………………… PALMITOLEIC ACID………………………………… OLEIC ACID………………………………………… ARACHIDONIC ACID………………………………… ALDEHYDE CARBOXYLIC ACIDS AND THEIR MEDICAL SIGNIFICANCE…………………………………………… GLYOXYLIC ACID……………………………………… KETO CARBOXYLIC ACIDS AND THEIR MEDICAL SIGNIFICANCE PYRUVIC ACID………………………………………… ACETOACETIC ACID…………………………………… OXALOACETIC AND 2-OXOGLUTARIC ACID………………… LEVULINIC ACID……………………………………… AROMATIC MONOCARBOXYLIC ACIDS AND THEIR MEDICAL SIGNIFICANCE……………………………………………… BENZOIC ACID………………………………………… P-AMINOBENZOIC ACID, ANESTHESINE, PROCAINE, AND LIDOCAINE………………………………………… HYDROXYCARBOXYLIC ACIDS AND THEIR MEDICAL SIGNIFICANCE ALIPHATIC HYDROXY MONOCARBOXYLIC ACIDS……………… GLYCOLIC ACID…………………………………… LACTIC ACID……………………………………… GLYCERIC ACID…………………………………… ?-HYDROXYBUTYRIC ACID…………………………… AROMATIC HYDROXY MONOCARBOXYLIC ACIDS……………… SALICYLIC ACID…………………………………… ACETYLSALICYLIC ACID……………………………… PAS……………………………………………… HYDROXYDI- AND TRICARBOXYLIC ACIDS…………………… MALIC ACID……………………………………… TARTARIC ACID……………………………………… CITRIC ACID……………………………………… 11 3 DICARBOXYLIC ACIDS AND THEIR MEDICAL SIGNIFICANCE………… ALIPHATIC DICARBOXYLIC ACIDS…………………………… OXALIC ACID…………………………………………… MALONIC ACID………………………………………… SUCCINIC ACID………………………………………… GLUTARIC ACID………………………………………… ADIPIC ACID…………………………………………… MALEIC ACID…………………………………………… FUMARIC ACID………………………………………… AROMATIC DICARBOXYLIC ACIDS…………………………… PHTHALIC ACIDS………………………………………… 11 4 CARBOXYLIC ACID DERIVATIVES AND THEIR MEDICAL SIGNIFICANCE SALTS, HALIDES, AND ANHYDRIDES…………………………… ESTERS……………………………………………………… NITROGLYCERIN………………………………………… DETERGENTS………………………………………………… AMIDES…………………………………………………… NITRILES…………………………………………………… 12 AMINES AND AMIDES………………………………………… 12 1 AMINES……………………………………………………… ALIPHATIC AMINES………………………………………… NOMENCLATURE AND CLASSIFICATION…………………… PHYSICAL PROPERTIES………………………………… CHEMICAL PROPERTIES………………………………… BASICITY………………………………………… FORMATION OF SCHIFF BASES………………………… REACTIONS WITH NITRIC ACID………………………… COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE………… METHYLAMINE…………………………………… NITROGEN MUSTARDS……………………… ……… SPERMINE AND SPERMIDINE………………… …… EDTA…………………………………………… AMINO ALCOHOLS……………………………………… ETHANOLAMINE AND CHOLINE……… …‘…………… ACETYLCHOLINE…………………………………… AROMATIC AMINES………………………………………… NOMENCLATURE AND CLASSIFICATION……………… … OXIDATION……………………………………… DIAZOTIZATION…………………………………… ANILINE AND ITS DERIVATIVES………………………… 12 2 AMIDES……………………………………………………… NOMENCLATURE AND CLASSIFICATION………………………… HYDROLYSIS…………………………………………… DEHYDRATION………………………………………… 13 HETEROCYCLIC COMPOUNDS………………………………… 13 1 NOMENCLATURE AND CLASSIFICATION…………………………… 13 2 PHYSICAL PROPERTIES………………………………………… 13 3 CHEMICAL PROPERTIES………………………………………… 13 4 FOUR-ATOMIC HETERORINGS AND THEIR MEDICAL SIGNIFICANCE… 13 5 FIVE-ATOMIC HETERORINGS AND THEIR MEDICAL SIGNIFICANCE… FIVE-ATOMIC HETERORINGS WITH ONE HETEROATOM………… PYRROLE……………………………………………… PYRROLINE………………………………………… PYRROLIDINE……………………………………… PORPHINE………………………………………… PORPHYRINS……………………………………… HEME B…………………………………………… FURAN………………………………………………… THIOPHENE……………………………………… FIVE-ATOMIC HETERORINGS WITH TWO HETEROATOMS………… PYRAZOLE………………………………………………… PHENAZONE…………………………………………… AMINOPHENAZONE………………………………… METAMIZOLE……………………………………… IMIDAZOLE………………………………………… … HISTAMINE………………………………………… OXAZOLE……………………………………………… THIAZOLE……………………………………………… 13 6 SIX-ATOMIC HETERORINGS AND THEIR MEDICAL SIGNIFICANCE…… SIX-ATOMIC HETERORINGS WITH ONE HETEROATOM…………… PYRIDINE……………………………………………… PIPERIDINE……………………………………… NICOTINAMIDE…………………………………… ISONIAZID………………………………………… PYRAN………………………………………………… SIX-ATOMIC HETERORINGS WITH TWO HETEROATOMS………… PYRIMIDINE…………………………………………… BARBITURIC ACID AND BARBITURATES………………… PYRAZINE……………………………………………… 13 7 POLYCYCLIC COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE…… INDOLE………………………………………… ………… BENZIMIDAZOLE…………………………………………… THIOPHENE IMIDAZOLE…………………………………… QUINOLINE AND ISOQUINOLINE…………………………… QUINUCLIDINE…………………………………………… TROPANE………………………………………………… CHROMANE……………………………………………… PURINE…………………………………………………… PTERIDINE………………………………………………… ISOALLOXAZINE…………………………………………… 14 ALKALOIDS…………………………………………………… 14 1 NOMENCLATURE AND CLASSIFICATION…………………………… 14 2 PHYSICAL PROPERTIES………………………………………… 14 3 CHEMICAL PROPERTIES………………………………………… 14 4 COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE……………… ALKALOIDS WITH NITROGEN HETEROCYCLES……………………… TROPANE ALKALOIDS…………………………………… ATROPINE………………………………………… SCOPOLAMINE…………………………………… HYOSCYAMINE…………………………………… COCAINE………………………………………… PIPERIDINE ALKALOIDS………………………………… LOBELINE………………………………………… CONIINE………………………………………… PYRIDINE ALKALOIDS…………………………………… RICININE………………………………………… NICOTINE………………………………………… ANABASINE………………………………………… ISOQUINOLINE ALKALOIDS……………………………… PAPAVERINE……………………………………… GLAUCINE………………………………………… MORPHINE………………………………………… CODEINE AND THEBAINE…………………………… HEROIN…………………………………………… QUINOLINE ALKALOIDS………………………………… QUININE…………………………………………… QUINIDINE………………………………………… INDOLE ALKALOIDS……………………………………… ERGOTAMINE……………………………………… YOHIMBINE………………………………………… RESERPINE……………………………………… STRYCHNINE……………………………………… VINCAMINE, VINBLASTINE, AND VINCRISTINE………… IMIDAZOLE ALKALOIDS………………………………… PILOCARPINE……………………………………… PURINE ALKALOIDS…………………………………… THEOPHYLLINE, THEOBROMINE, AND CAFFEINE……… ALKALOIDS WITH NITROGEN IN THE SIDE CHAIN……………… ?-PHENYLETHYLAMINE ALKALOIDS………………………… EPHEDRINE……………………………………… MESCALINE………………………………………… AMPHETAMINE…………………………………… TROPOLONE ALKALOIDS………………………………… COLCHICINE……………………………………… FURAN ALKALOIDS……………………………………… MUSCARINE……………………………………… BENZYLAMINE ALKALOIDS……………………………… CAPSAICIN………………………………………… PSEUDOALKALOIDS………………………………………… DITERPENOID ALKALOIDS……………………………… ACONITINE………………………………………… DELPHININE……………………………………… STEROID ALKALOIDS…………………………………… SOLANIDINE………………………………………… 15 CARBOHYDRATES…………………………………………… 15 1 NOMENCLATURE AND CLASSIFICATION…………………………… 15 2 MONOSACCHARIDES…………………………………………… OPTICAL ISOMERISM…………………………………… MUTAROTATION………………………………………… CYCLIZATION OF MONOSACCHARIDES……………………… HAWORTH’S PROJECTION AND CHAIR FORM………………… REACTIONS OF CARBONYL GROUP…………………………… OXIDATION………………………………………… REDUCTION………………………………………… NUCLEOPHILIC ADDITION…………………………… REACTIONS OF ALCOHOL GROUP………………………… ACETALIZATION…………………………………… ESTERIFICATION…………………………………… AMINATION………………………………………… ENOLIZATION……………………………………… GLUCOSE……………………………………………… FRUCTOSE…………………………………………… MANNOSE……………………………………………… GALACTOSE…………………………………………… RIBOSE………………………………………………… DEOXYRIBOSE………………………………………… 15 3 DISACCHARIDES……………………………………………… REDUCING DISACCHARIDES AND THEIR MEDICAL SIGNIFICANCE MALTOSE……………………………………………… LACTOSE……………………………………………… CELLOBIOSE…………………………………………… NON-REDUCING DISACCHARIDES AND THEIR MEDICAL SIGNIFICANCE……………………………………………… SUCROSE……………………………………………… INVERT SUGARS…………………………………………… 15 4 POLYSACCHARIDES……………………………………………… HOMOPOLYSACCHARIDES AND THEIR MEDICAL SIGNIFICANCE… STARCH………………………………………………… DEXTRAN……………………………………………… GLYCOGEN……………………………………………… CELLULOSE……………………………………………… INULIN………………………………………………… HETEROPOLYSACCHARIDES AND THEIR MEDICAL SIGNIFICANCE… GLYCOSAMINOGLYCANS………………………………… CHONDROITIN SULFATES………………………………… DERMATAN SULPHATE…………………………………… HEPARIN……………………………………………… HYALURONIC ACID……………………………………… CHITIN………………………………………………… GLYCOPROTEINS…………………………………………… GLYCOLIPIDS……………………………………………… 16 LIPIDS………………………………………………………… 16 1 NOMENCLATURE AND CLASSIFICATION…………………………… 16 2 PHYSICAL PROPERTIES………………………………………… 16 3 CHEMICAL PROPERTIES………………………………………… HYDROLYSIS………………………………………………… SAPONIFICATION…………………………………………… RANCIDIFICATION…………………………………………… HYDROGENATION…………………………………………… 16 4 COMPOUNDS AND THEIR MEDICAL SIGNIFICANCE………………… FATTY ACIDS……………………………………………… ESSENTIAL FATTY ACIDS………………………………… ?-6-FATTY ACIDS…………………………………… LINOLEIC ACID………………………………… GAMMA-LINOLENIC ACID………………………… DIHOMO-?-LINOLENIC ACID………………………… ?-3-FATTY ACIDS…………………………………… ALPHA-LINOLENIC ACID………………………… EICOSAPENTAENOIC ACID………………………… DOCOSAHEXAENOIC ACID………………………… WAXES………………………………………………… GLYCEROLIPIDS…………………………………………… TRIACYLGLYCEROLS……………………………………… PHOSPHOLIPIDS…………………………………………… GLYCEROPHOSPHOLIPIDS………………………………… CEPHALINS………………………………………… LECITHINS………………………………………… CARDIOLIPINS……………………………………… SPHINGOLIPIDS………………………………………… CEREBROSIDES AND GANGLIOSIDES…………………… STEROIDS…………………………………………………… STEROLS………………………………………………… CHOLESTEROL……………………………………… BILE ACIDS…………………………………………… TERPENOIDS………………………………………………… SACCHAROLIPIDS…………………………………………… POLYKETIDES……………………………………………… 16 5 BIOLOGICAL MEMBRANES……………………………………… 16 6 SIGNALING……………………………………………………… 16 7 ENERGY STORAGE……………………………………………… 16 8 NUTRITION AND HEALTH………………………………………… 16 9 FISH OILS AND HEART DISEASES………………………………… SUMMARY…………………………………………………………………… 17 AMINO ACIDS………………………………………………… 17 1 NOMENCLATURE AND CLASSIFICATION…………………………… 17 2 PHYSICAL PROPERTIES………………………………………… OPTICAL ACTIVITY…………………………………………… 17 3 CHEMICAL PROPERTIES………………………………………… IONIZATION………………………………………………… ISOMERISM………………………………………………… PEPTIDE GROUP…………………………………………… DISULFIDE BOND…………………………………………… 17 4 PROTEINOGENIC AMINO ACIDS AND THEIR MEDICAL SIGNIFICANCE HYDROPHOBIC AMINO ACIDS………………………… …… HYDROPHILIC AMINO ACIDS………………………………… ?-AND ?-AMINO ACIDS…………………………………… 17 5 NON-PROTEINOGENIC AMINO ACIDS AND THEIR MEDICAL SIGNIFICANCE………………………………………………… 17 6 ESSENTIAL AMINO ACIDS AND THEIR MEDICAL SIGNIFICANCE……… 17 7 DRUGS DERIVATIVES OF AMINO ACIDS…………………………… 18 PEPTIDES AND PROTEINS……………………………………… 18 1 PEPTIDES AND THEIR MEDICAL SIGNIFICANCE……………………… OLIGOPEPTIDES…………………………………………… POLYPEPTIDES……………………………………………… GLUCAGON…………………………………………… SOMATOSTATIN………………………………………… CALCITONIN…………………………………………… GHRELIN……………………………………………… 18 2 PROTEINS AND THEIR MEDICAL SIGNIFICANCE……………………… SIMPLE PROTEINS………………………………… …… COMPLEX PROTEINS…………………………………… PRIMARY STRUCTURE……………………………………… SECONDARY STRUCTURE…………………………………… FIBROUS PROTEINS…………………………………… TERTIARY STRUCTURE……………………………………… GLOBULAR PROTEINS…………………………………… INSULIN…………………………………………… QUATERNARY STRUCTURE…………………………………… SOLUBILITY…………………………………………… TITRATION……………………………………………… ISOELECTRIC POINT……………………………………… ISOIONIC POINT………………………………………… NATIVE AND DENATURED PROTEINS…………………… …… DENATURING FACTORS………………………………… HEAT……………………………………………… RADIATION………………………………………… PH………………………………………………… ALCOHOLS………………………………………… HEAVY METAL IONS………………………………… ALKALOIDS………………………………………… REDUCING AGENTS………………………………… PROTEIN PURIFICATION……………………………………… PROTEINS IN THE CLINICAL PRACTICE………………………… ALBUMIN……………………………………………… GLOBULINS…………………………………………… FIBRINOGEN…………………………………………… HEMOGLOBINS………………………………………… C-REACTIVE PROTEIN…………………………………… 19 ENZYMES……………………………………………… …… HISTORY……………………………………………………… …… 19 1 NOMENCLATURE AND CLASSIFICATION……………………… ……… FIRST GROUP: OXIDOREDUCTASES (EC 1)……………………… SECOND GROUP: TRANSFERASES (EC 2)……………………… THIRD GROUP: HYDROLASES (EC 3)………………………… FOURTH GROUP: LYASES (EC 4)…………………………… FIFTH GROUP: ISOMERASES (EC 5)……………………… … THYMINE, URACIL, AND CYTOSINE……………… ……… PURINE NUCLEOBASES……………………………………… ADENINE AND GUANINE………………………………… MINOR NUCLEOBASES……………………………………… OTHER PURINE DERIVATIVES………………………………… 20 3 NUCLEOSIDES AND THEIR MEDICAL SIGNIFICANCE………………… 20 4 NUCLEOTIDES AND THEIR MEDICAL SIGNIFICANCE………………… (MONO)NUCLEOTIDES……………………………………… CYCLIC (MONO)NUCLEOTIDES……………………………… NUCLEOSIDE DI- AND TRIPHOSPHATES……………………… 21 NUCLEIC ACIDS……………………………………………… 21 1 NOMENCLATURE AND CLASSIFICATION…………………………… 21 2 DEOXYRIBONUCLEIC ACIDS AND THEIR MEDICAL SIGNIFICANCE…… SPECIFIC AND REPETITIVE SEQUENCES IN DNA……………… SUPERCOILING OF DNA…………………………………… DENATURATION AND RENATURATION……………………… MUTATIONS…………………………………………… FINGERPRINTING……………………………………… RECOMBINANT TECHNOLOGY………………………………… 21 3 RIBONUCLEIC ACIDS AND THEIR MEDICAL SIGNIFICANCE…………… RIBOSOMAL RNA…………………………………………… MESSENGER RNA…………………………………………… TRANSFER RNA…………………………………………… SMALL NUCLEAR RNA……………………………………… 21 4 GENES, CENTRAL DOGMA IN MOLECULAR BIOLOGY, AND MEDICAL SIGNIFICANCE………………………………………………… SIXTH GROUP: LIGASES (EC 6)…………………………… SEVENTH GROUP: TRANSLOCASES (EC 7)……………………… 19 2 MECHANISM OF ENZYME ACTION……………………………… CATALYTIC SITE…………………………………………… COENZYMES AND PROSTHETIC GROUPS…………………… SUBSTRATE BINDING………………………………………… KEY-LOCK THEORY……………………………………… INDUCED-FIT THEORY…………………………………… 19 3 ENZYME SPECIFICITY…………………………………………… SUBSTRATE SPECIFICITY…………………………………… REACTION SPECIFICITY……………………………………… 19 4 ENZYME TYPES………………………………………………… ALLOSTERIC ENZYMES……………………………………… ISOENZYMES……………………………………………… IMMOBILIZED ENZYMES…………………………………… 19 5 KINETICS OF SIMPLE ENZYME REACTIONS………………………… 19 6 THERMODYNAMICS OF ENZYME REACTIONS………………………… 19 7 ENZYME ACTIVITY AND ITS MEDICAL SIGNIFICANCE………………… UNITS OF ENZYME ACTIVITY………………………………… FACTORS INFLUENCING THE ENZYME ACTIVITY………………… EFFECT OF TEMPERATURE ON ENZYME ACTIVITY…………… EFFECT OF PH ON ENZYME ACTIVITY……………………… ENZYME ACTIVATION…………………………………… ENZYME INHIBITION…………………………………… REVERSIBLE INHIBITION…………………………… COMPETITIVE INHIBITION……………………… NON-COMPETITIVE INHIBITION…………………… UNCOMPETITIVE INHIBITION……………………… ALLOSTERIC INHIBITION………………………… IRREVERSIBLE INHIBITION…………………………… 19 8 MEDICAL SIGNIFICANCE………………………………………… 20 NUCLEOBASES, NUCLEOSIDES, AND NUCLEOTIDES……………… 20 1 NOMENCLATURE AND CLASSIFICATION…………………………… 20 2 NUCLEOBASES AND THEIR MEDICAL SIGNIFICANCE………………… PYRIMIDINE NUCLEOBASES