Download Aromatic carboxylic acids

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