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GOMEL STATE MEDICAL UNIVERSITY General and Bioorganic Chemistry t department Structure of compounds studied in bioorganic chemistry 1 study year Gomel 2011 AROMATIC & CONJUGATED MOLECULAS NH2 OH CH Benzene Phenol Aniline Cyclopentadienyl anion N N N H N H Pyrrole N pyrozole Imidozole N N N Pyrimidine Antracene Pyridine S Furan N N N O H Thiofene + N H CH Purine Fhenantrene Cycloheptatrienyl cation Naphthalene β-Carotene CH2OH Vitamin А (retinol) 1 Azylene ALCOHOLS CH3-CH2OH Ethanol CH2-OH 5 5 CH3OH Methanol +3H2O t, H+ CH2- OH 35 OH OH OH OH CH OH OH OH OH CH3 CH3 CH3 Glycerol Xylitol CH CH2 Menthol NH - CH3 CH OH CH2 NH2 OH OH OH OH OH Adrenaline OH Noradrenalin CH2 N+ CH2 CH3 CH3 CH3 Choline CH2 CH2 OH OH Ethyldiol-1,2 OH HO OH OH HO OH CH2 CH2 OH NH2 Ethanolamine or Colamine Inosit CH2OH CH3(CH2)12 CH OH H OH CH - OH + 3 C17H35COOH CH2-CH-CH-CH-CH2 H NaBH4 HO CH CH CH OH Sphingosine NH2 OH H H OH H OH CH2OH Sorbitol 2 CH2OH ALDEHYDES & KETONES O O H C CH3 H Methanal or formaldehyde C H Ethanal or acetaldehyde O O CH3 CH2 C CH3 H Propanal or propionic aldehyde CH3 CH2 CH2 C CH2 H Butanal or butyric aldehyde O CH2 CH2 CH3 C CH3 C O H Pentanal or valeric aldehyde acetone O O C CH CH3 CH CH2 = CH - C H H Propenal or Acroleine C Butene-2-al or Crotonic aldehyde O CH2 CH H OH Benzoic aldehyde OH H Glyceraldehyde CARBOXYLIC ACIDS Saturated monocarboxylic acids HCOOH CH3COOH CH3CH2COOH CH3CH2CH2COOH CH3CH2CH2CH2COOH CH3CH2CH2CH2CH2COOH C 1 5 H 3 1 COOH C17H35COOH O C Formic or methanoic acid Acetic or ethanoic acid Propionoic or propanoic acid Butyric or Butanoic acid Valeric or Pentanoic acid Caproic or Hexanoic acid Palmitinic acid Steric acid 3 Saturated dicarboxylic acids HOOC HOOC HOOC HOOC Oxalic or ethanedioic acid COOH CH2 COOH Malonic or propanedioic acid CH2 CH2 COOH Succinic or butanedioic acid CH2 CH2 CH2 COOH Glutaric or pentanedioic acid Aromatic carboxylic acids COOH CH2 COOH COOH COOH Benzoic or Benzene carboxylic acid Phenyl-acetic acid Terephthalic acid Hetero functional aromatic carboxylic acids NH2 NH2 NH2 O C OH OH p- sulfanilic acid salicylic acid O SO2 - NH - R NH2 Nicotinic acid PABA (para-aminobenzoic acid) Unsaturated carboxylic acid H2C = CH – COOH CH3CH=CHCOOH CH3(CH2)7CH=CH(CH2)7COOH O -C COOH O - C - CH3 N SO2NH2 C C OH OH SO3H O O O C C17H33COOH Acrylic acid Propenoic acid Crotonic acid Butane-2-oic acid Oleic acid CH3(CH2)4CH=CH-CH2-CH=CH(CH2)7COOH C17H31COOH Linoleic acid CH3CH2CH=CH-CH2-CH=CH-CH2-CH=CH(CH2)7COOH C17H29COOH Linolenic acid CH3(CH2)4CH=CH-CH2-CH=CH-CH2-CH=CH-CH2-CH=CH(CH2)3COOH C19H31COOH Arachidonic acid 4 NH2 Unsaturated dicarboxylic acids H C COOH H H C C COOH HOOC C HOOC Maleic acid or cis-butenedioic acid H Fumaric acid or trans- butenedioic acid Hydroxy carboxylic acids CH3 CH COOH НООС―СН― СН2― СООН COOH ǀ OH OH Lactic acid 2-Hydroxy propanoic acid Malic acid CH CH OH OH COOH Tartaric acid COOH COOH CH2 C CH2 COOH OH Citric acid Keto carboxylic acids or oxo carboxylic acid CH3 C COOH CH3 O COOH CH2 COOH C Acetoacetic acid CH2 CH2 COOH CH2 COOH Oxaloacetic acid O C O C O O Pyruvic acid COOH C COOH H α-Ketoglutaric acid glyoxilic acid OTHER COMPOUNDS О СН3 CH2 С CH2 CH2 COOH NH2 γ-aminobutyric acid SСoA Acetyl Co A (Acetyl coenzyme A) 5 Cl CH2 SH CH SH CH2 SO3Na Cl Cl Cl Cl Cl BAL Hexachloran CHCl3 CHI3 Chloroform Iodoform LIPIDS O H2C O O C R C O HC O R' H2C O P O-X OH O General formula for phospholipids CH2 O R2 C O O CH CH2 C O O P O- CH2 R2 C O O CH CH2 C R1 O O P O CH2 CH2 NH2 phosphatidylethanolamine (cephaline) O O R1 O O- CH2 CH2 CH3 + N CH3 CH3 Phosphatidylcholine (lecithin) 6 H2 O3H CH3 CH3 CH-CH2-CH2-CH2-CH-CH3 CH3 CH3 A C B HO Cholesterol CH3 Steroid ring O O C CH2 CH2 + N CH3 CH3 CH3 Acetylcholine HETERO FUNCTIONAL O O O C C OH COMPOUNDS C2H5 C O -C2H5 O - CH2 - CH2 - N C2H5 NH2 NH2 NH2 Anesthesine Ethyl Ester of PABA Novocain Ester of PABA and N-diethylaminoethanol NH2 O NH2 O C C OH OH O - C - CH3 OH O SO2NH2 Sulfanilamide SO2 - NH - R Aspirin (Acetylsalicylic acid) 7 D CH2-CH2-NH2 -COOH O - CO2 C COOH N 2 NH2 H N N Tryptamine H Nicotinic acid O H C Nicotinamide O N HO CH2OH O N H3C N Pyridoxine Barbituric acid O H O H O O H N N H N N N O H N N H N O H Hypoxanthine 6-oxopurine Xanthine 2,6-dioxopurine N N E + - CO2 CH2-CH-COOH H H N H H Histamine CH2SO3Na N Serotonin O H C 2H 5 CH3 O N N N O H H CH2-CH2-NH2 N H Indole H3C HO N NH2 N E CH2 - CH2 - NH2 N H Uric acid 2,6,8-trioxopurine SE + N N N C 6H 5 CH3 O N O H C6H5 Analgine Phenobarbital 8 CARBOHYDRATES Monosaccharides CHO H CHO CHO OH H OH HO H H H HO H HO H OH HO H H OH H OH H OH H OH HO CH2OH CH2OH CH2OH D-glucose D-galactose Epimer of glucose at C-4 CH2OH C H H O HO D-mannose Epimer of glucose at C-2 C O C CH2 O H H OH H OH H OH H OH H OH H OH H OH CH2OH CH2OH CH2OH D –ribose D-fructose D - deoxyribose Di- and Polysaccharides 6 6 CH2OH CH2OH O 5 4 OH 5 1 2 3 OH OH CH2OH 4 O OH 3 O OH 1 OH OH O HOCH2 O HO 2 Sucrose OH CH2OH 1 1 2 OH Maltose 9 OH O CH2OH HO CH2OH O O OH Glycosidic group OH O OH OH OH Lactose CH2OH CH2OH CH2OH O O O OH OH OH O O O H OH OH OH Amylase CH2OH CH2OH O O OH OH O O OH O OH CH2OH CH2 CH2OH O O O OH OH OH O O O OH OH OH OH Amylopectin O OH O O O OH CH2OH CH2OH CH2OH OH O OH OH O OH Cellulose 10 α(1→6) glycosidic bond 6 CH2 CH2 CH2 O O O OH O O OH 1 3 OH OH OH OH OH OH O α (1→3) glycosidic bond CH2 O O OH 1 OH OH Dextrans COOH H OH COOH H OH HO H HO H H OH OH H OH OH H H COOH CH2OH D-Gluconic acid D-Glucaric acid 11 α–AMINO ACIDS O I. ALIPHATIC AMINO ACIDS MONOAMINO MONOCARBOXYLIX ACIDS H2N - CH2 - COOH Amino acetic acid, 2-amino ethanoic acid, Glycine (Gly) CH3 - CH - COOH │ NH2 α – aminopropionic acid,2-aminopropanoic acid, Alanine (Ala) CH2 - CH - COOH │ │ OH NH2 α-amino-β-hydroxy propionic acid, 2-amino-3-hydroxypropanoic acid, serine, (Ser) CH2 - CH - COOH │ │ SН NН2 α-amino-β-thio propionic acid, 2- amino-3-mercaptopropanoic acid, Cystein (Cys) CH2 - CH2 - CH - COOH | | S-CH3 NH2 α-amino-γ-methylthiobutyric acid, 2-amino-4-methylthiobutanoic acid, Methionine (Met) CH3 - CH - CH - COOH | | СН3 NН2 α-aminoisovaleric acid, 2-amino-3-methylbutanoic acid, Valine (Val) CH3 - CH - CH - COOH | | OH NН2 α-amino-β-hydroxybutyric acid, 2-amino-3-hydroxybutanoic acid, Threonine (Thr) CH3 - CH - CH2 - CH - COOH │ │ CH3 NН2 α-amino isocaproic acid, 2-amino-4-methylpentanoic acid, Leucine (Leu) 12 CH3 - CH2 - CH - CH - COOH │ │ CH NН2 α-amino-β-methylvaleric acid, 2-amino-3-methylpentanoic acid, Isoleucine (ILe) MONOAMINO DICARBOXYLIC ACIDS HOOC - CH2 - CH - COOH │ NН2 α-amino succinic acid, 2-amino butanedioic acid, Aspartic acid (Asp) HOOC - CH2 - CH2 - CH - COOH │ NН2 α-aminoglutaric acid, 2-aminopentanedioic acid, Glutamic acid (Glu) O H2N C CH2 CH COOH NH2 Aspartic acid amide, Asparagine (Asn) O H2 N C CH2 CH2 CH NH2 COOH Glutamic acid amide, Glutamine (Gln) DIAMINO MONOCARBOXYLIC ACIDS H2N - CH2 - CH2 - CH2 - CH2 - CH - COOH │ NН2 α,ε –diamino caproic acid, 2,6-diaminohexanoic acid, Lysine (Lys) H2N - C - NH - CH2 - CH2 - CH2 - CH – COOH ║ │ NН NН2 α-amino-Δ –guanidyl valeric acid, 2-amino-5-guanidylpentanoic acid, Arginine (Arg) 13 II. AROMATIC Α-AMINO ACIDS CH2 - CH - COOH NH2 CH2 - CH - COOH NH2 HO α-amino-β-phenyl propionic acid, 2-amino-3-phenyl propanoic acid, Phenylalanine (Phe) 2-amino-3-(4-hydroxyphenyl)-propanoic acid, Tyrosine (Tyr) III. HETEROCYCLIC α-AMINO ACIDS N -amino-- imidazolyl propionic acid, 2-amino-3-imidazolyl propanoic acid Histidine (His) CH2 - CH - COOH N H NH2 CH2 -CH - COOH - amino-- indolyl propionic acid 2-amino-3-indolyl propanoic acid Tryptophan (Trp) NH2 N H IV. IMINO ACIDS COOH Pyrrolidine-2-carboxylic acid, Proline (Pro) N H OH 4-hydroxy pyrrolidine-2-carboxylic acid, Hydroxy proline (НО-Pro) COOH N H 14 NUCLEIC ACIDS THE PURINES BASES O NH2 6 1 7 N N N9 H 3 H2N Adenine – A 6-aminopurine 3 5 NH 6 2 N1 H N 4 N9 H 3 Guanine – G 2-amino -6-oxopurine THE PYRIMIDINES BASES O 4 NH2 O H3C 4 5 4 3 5 NH 6 2 6 O N1 H O N1 H Thymine – T 5-methyl -2,4-dioxopirimidine Ester bond N O N N N-glycosidic bond OCH2 O OH OH OH Adenosine-5’-monophosphate or AMP 15 O Cytosine – C 4-amino - 2-oxopirimidine NH2 N P 3 N 2 uracil – U 2,4-dioxopirimidine HO 7 8 2 4 N 5 HN 8 2 6 1 N 5 NH2 N O O N O N HO - P - O - P - O - P - O - CH 2 OH OH N O OH OH OH ATP NH2 N N 5' O N N CH2 O O 3' P HO OH O Adenosine -3‘-5‘-cyclic monophosphate or cyclic AMP or c-АМP NH2 O C N N NH2 O O + N N H H CH2 - O - P - O - P - O - CH2 O OH H OH O OH H OH H H OH Nicotinamide adenine dinucleotide or NAD+ 16 H OH N NAMES OF COMPOUNDS ARE IN ALPHABETIC ORDER Acetaldehyde Acetic or Ethanoic acid Acetoacetic acid Acetone Acetyl coenzyme Acetylcholine Acroleine Acrylic acid Adenine – A Adenosine-5’-monophosphate Adrenaline Alanine (Ala) Amylase Amylopectin Analgine Aniline Antracene Arachidonic acid Arginine (Arg) Asparagine (Asn) Aspartic acid (Asp) Aspirin (Acetylsalicylic acid) Aspirin (Acetylsalicylic acid) ATP Azylene BAL Barbituric acid Benzene Benzoic Benzoic aldehyde Butanal Butene-2-al butyric aldehyde Butyric or Butanoic acid Carotene-β Cellulose Chloroform Cholesterol Choline Citric acid Colamine Lactic acid 3 3 5 3 5 7 3 4 14 15 2 12 10 10 8 1 1 4 13 13 13 7 7 16 1 6 8 1 4 3 3 3 3 3 1 10 6 7 2 5 2 17 5 Crotonic acid Crotonic aldehyde cyclic AMP Cycloheptatrienyl cation Cyclopentadienyl anion Cystein (Cys) Cytosine – C Deoxyribose Dextrans Ethanal Ethanol Ethanolamine Ethyldiol-1,2 Fhenantrene Formaldehyde Formic or Methanoic acid Fructose Fumaric acid Furan Galactose Glucaric acid Gluconic acid glucose Glutamic acid (Glu) Glutamine (Gln) Glutaric or pentanedioic acid Glyceraldehyde Glycerol Glycine (Gly) Glyoxalic acid Guanine – G Hexachloran Histamine Histidine (His) Hydroxy proline (НО-Pro) Hypoxanthine Imidozole Indole Inosit Iodoform Isoleucine (ILe) 4 3 16 1 1 12 15 9 11 3 1 2 2 1 3 3 9 5 1 9 11 11 9 13 13 4 3 2 12 5 14 6 8 14 14 8 1 8 2 6 13 Pyridine 1 Lactose Leucine (Leu) Linoleic acid Linolenic acid Lysine (Lys) Maleic acid Malic acid Malonic or propanedioic acid Maltose Mannose Menthol Methanal Methanol Methionine (Met) Naphthalene Nicotinamide Nicotinamide adenine dinucleotide or NAD+ Nicotinic acid Nicotinic acid Noradrenalin Novocain Oleic acid Oxalic or ethanedioic acid Oxaloacetic acid p- Sulfanilic acid Palmitinic acid p-Aminobenzoic acid Pentanal Phenobarbital Phenol Phenyl-acetic acid Phenylalanine (Phe) Phosphatidylcholine (lecithin) Phosphatidylethanolamine (cephaline) Phthalic acid Proline (Pro) Propanal Propenal propionic aldehyde Propionoic or Propanoic acid Purine 10 12 4 4 13 5 5 4 9 9 2 3 2 12 1 8 16 Pyridoxine Pyrimidine Pyrozole Pyrrole Pyruvic acid Ribose Salicylic acid Serine (Ser) Serotonin Sorbitol Sphingosine Steric acid Steroid ring Succinic or butanedioic acid Sucrose Sulfanilamide Tartaric acid 8 1 1 1 5 9 4 12 8 2 2 3 7 4 9 7 5 4 8 2 7 4 4 5 4 3 4 3 8 1 4 14 6 6 4 14 3 3 3 3 1 Thiofene Threonine (Thr) Thymine – T Tryptamine Tryptophan Tryptophan (Trp) Tyrosine (Tyr) Uracil – U Uric acid valeric aldehyde Valeric or Pentanoic acid Valine (Val) Vitamin А (retinol) Xanthine Xylitol α-Ketoglutaric acid γ-aminobutyric acid 1 12 15 8 8 14 14 15 8 3 3 12 1 8 2 5 5 18