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Amino Acids and Derivatives

Amino acids and their derivatives belong to a compound containing both amino group and carboxyl group. They are presented in both the form of free-state and bound-state in vivo. Free amino acids are distributed in all kinds of animal cells and body fluids with the bound amino acids being the mainly basic components of proteins and peptides.

Natural amino acids act as colorless crystalline materials with relatively high melting points being mostly above 200 ℃. They are usually soluble in water but insoluble in non-polar organic solvents. However, tyrosine and cystine are insoluble in water; proline and hydroxyl proline are soluble in ethanol and ether. All amino acids are soluble in strong acid and alkali solution.

According to the polar characterization of the R group of the side chain of the α-amino acid; those 20 common amino acids that constitute protein can be divided into four groups:
① Amino acids with R group being non-polar; There are 8 kinds in total, wherein five kinds have aliphatic side chains, namely alanine, leucine, isoleucine, valine and proline; two kinds are aromatic amino acids, phenylalanine and tryptophan; one kind belongs to sulfur-containing amino acid, namely methionine; amino acids belonging to this group have lower water solubility than polar R-group amino acid; proline is generally different with α-amino acid, it is formed through the substitution of one hydrogen atom of the amino acid with the side chains of the α- amino acid, belonging actually to imino acid.
② Amino acids with polar but non-charged R group; There are seven kinds in total, namely serine, threonine and tyrosine with R group having hydroxy group; cysteine with R group having a mercapto group of cysteine; glutamine and asparagine with R-group containing amide group, another amino acid is glycine ; glycine molecule has no R group, but having certain polarity, and thus being classified into this group; the side chains in this group of amino acid contain unassociated polar groups and can form hydrogen bonds with water, and is easily soluble in water.
③Amino acids with R group being positively charged amino acids. There are three kinds in total, namely, lysine, arginine, and histidine; they carry positive charge at pH7.0 and are also known as alkaline amino acids.
④Amino acids with R group being negatively charged. There are two kinds in total, namely glutamate and aspartate; at pH7.0, the molecules are negatively charged, also known as acidic amino acids. The formula, abbreviations symbols and related constants of 20 kinds of amino acid structures can be seen from the table. In addition to the 20 common amino acids mentioned above, there are also diiodotyrosine, thyroxine, hydroxyproline and hydroxylysine existing in certain proteins. In addition to amino acids involved in protein composition, it has been also found of more than 200 kinds of other kinds amino acids in a variety of tissues and cells; these amino acids are mostly derivatives of those α- amino acid composition of proteins.

However, there are some β-, γ- or δ- amino acids and some amino acids belong to D-type amino acids such as [beta]-alanine, [gamma]-aminobutyric acid and the phenylalanine contained in the antibiotics gramicidin-S, the D-alanine and D-glutamate contained in Gram-positive bacteria cell wall. Some non-protein amino acids can act as metabolically important precursors or intermediates, wherein β-alanine is the precursors of vitamin pantothenic acid; ornithine, and citrulline are the precursors in the synthesis of arginine; [gamma]-aminobutyric acid is the chemical neurotransmitter. Plants contain a large amount of non-protein amino acids, belonging to plant secondary substances, such as theanine, canavanine, djenkolic acid, β- Cyanoalanine and so on.

In addition to 20 kinds of amino acids found in the body and animal protein products, it has been found of nearly 200 kinds of other kinds of amino acids in nature. Most of them have been discovered in the plant kingdom and have complex molecular structures with no relation with the protein metabolism. There have been less that have been seen in the animal kingdom with some of them being originated from the chemical modification of certain incorporated amino acids in the specific proteins, for example, the proline and lysine contained in collagen protein are often partially subject to re-hydroxylation of hydroxyproline and hydroxylysine; Another example is that there are often a small amount of lysine and histidine contained in actin and myosin protein containing hypermethylated εN methyl-lysine and 3N-histidine; it has been also found in the histone protein that the ∈ amino group contained in lysine is acetylated and the OH group in the serine is phosphorylated; thyroglobulin contains iodinated tyrosine and thyronine iodide; The heavy chain of τ myosin and the N-terminal of certain proteins contain pyroglutamate formed by glutamine; there also exists the cystine constituting of two cysteine molecules in the general protein.

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Structure Chemical Name CAS MF
2-AMINO-3-METHYLBENZYL ALCOHOL 2-AMINO-3-METHYLBENZYL ALCOHOL 57772-50-6 C8H11NO
D(-)PENICILLAMINE HYDROCHLORIDE D(-)PENICILLAMINE HYDROCHLORIDE 2219-30-9 C5H12ClNO2S
BOC-PRO-PRO-OH BOC-PRO-PRO-OH 15401-08-8 C15H24N2O5
H-MET-NH2 HCL H-MET-NH2 HCL 16120-92-6 C5H13ClN2OS
Methyl (S)-3-acetamido-3-phenylpropanoate Methyl (S)-3-acetamido-3-phenylpropanoate 67654-58-4 C12H15NO3
Diethyl N-[5-methylamino-2-thenoyl]-L-glutamate Diethyl N-[5-methylamino-2-thenoyl]-L-glutamate 112889-02-8 C15H22N2O5S
1-N-CBZ-4-HYDROXY-BETA-PROLINE 1-N-CBZ-4-HYDROXY-BETA-PROLINE C13H15NO5
2,5-Difluoro-L-phenylalanine 2,5-Difluoro-L-phenylalanine 31105-92-7 C9H9F2NO2
DL-P-Hydroxyphenylglycine DL-P-Hydroxyphenylglycine C8H9NO3
L-Lysine S-(carboxymethyl)-L-cysteine L-Lysine S-(carboxymethyl)-L-cysteine 49673-81-6 C11H23N3O6S
methyl L-tryptophanate methyl L-tryptophanate 4299-70-1 C12H14N2O2
2-AMINO-5-CHLOROBENZYL ALCOHOL 2-AMINO-5-CHLOROBENZYL ALCOHOL 37585-25-4 C7H8ClNO
L-Alninebenzylester-p-toluene sulfonate salt L-Alninebenzylester-p-toluene sulfonate salt 42584-62-6 C17H21NO5S
3-Phenyl-L-serine 3-Phenyl-L-serine 6254-48-4 C9H11NO3
5-AMINO-2-CHLOROBENYL ALCOHOL 5-AMINO-2-CHLOROBENYL ALCOHOL 89951-56-4 C7H8ClNO
N-BSMOC-L-LEUCINE N-BSMOC-L-LEUCINE 197245-21-9 C16H19NO6S
Z-L-Alanine N-carboxyanhydride Z-L-Alanine N-carboxyanhydride 125814-23-5 C12H11NO5
D-4-Aminophenylglycine D-4-Aminophenylglycine 35619-39-7 C8H10N2O2
(2S)-2-Amino-3-dimethylaminopropanoic acid (2S)-2-Amino-3-dimethylaminopropanoic acid 10138-99-5 C5H12N2O2
1H-Pyrazole-3-carboxylicacid,5-amino- 1H-Pyrazole-3-carboxylicacid,5-amino- 124004-31-5 C4H5N3O2
RINK AMIDE LINKER RINK AMIDE LINKER 126828-35-1 C32H29NO7
AC-LYS(AC)-D-ALA-D-ALA-OH AC-LYS(AC)-D-ALA-D-ALA-OH 24570-39-6 C16H28N4O6
Cyclohexanecarboxylic acid, 3-amino-, (1S-cis)- (9CI) Cyclohexanecarboxylic acid, 3-amino-, (1S-cis)- (9CI) 81131-40-0 C7H13NO2
Benzoic acid, 2-[(2-nitroethylidene)amino]- (9CI) Benzoic acid, 2-[(2-nitroethylidene)amino]- (9CI) 121845-92-9 C9H8N2O4
L-HYDROXYLYSINE DIHYDROCHLORIDE L-HYDROXYLYSINE DIHYDROCHLORIDE 172213-74-0 C6H15ClN2O3
FMOC-PRO-OPFP FMOC-PRO-OPFP 86060-90-4 C26H18F5NO4
(R)-3-(3-BROMOPHENYL)-BETA-ALANINE
(R)-3-(3-BROMOPHENYL)-BETA-ALANINE 788153-27-5 C9H10BrNO2
(4S)-4-METHYL-L-PROLINE
(4S)-4-METHYL-L-PROLINE 6734-41-4 C6H11NO2
Poly-D-leucine Poly-D-leucine 63038-44-8 (C6H11NO)n
H-Ser-OtBu · HCl H-Ser-OtBu · HCl 106402-41-9 C7H16ClNO3
N-BSMOC-L-ALANINE N-BSMOC-L-ALANINE 197245-15-1 C13H13NO6S
D-PROLINE TERT-BUTYL ESTER HYDROCHLORIDE D-PROLINE TERT-BUTYL ESTER HYDROCHLORIDE 184719-80-0 C9H18ClNO2
1-BENZYL D-ASPARTATE 1-BENZYL D-ASPARTATE 79337-40-9 C11H13NO4
N-[1-[2-(2-PYRIDYLCARBOXAMIDO)PHENYL]ETHYLIDENE] GLYCINATO] N-[1-[2-(2-PYRIDYLCARBOXAMIDO)PHENYL]ETHYLIDENE] GLYCINATO] 264921-97-3 C16H13N3NiO3
METHYL 2-AMINO-3-(4-HYDROXYPHENYL)PROPANOATE METHYL 2-AMINO-3-(4-HYDROXYPHENYL)PROPANOATE 18869-47-1 C10H13NO3
BOC-BETA-TBU-D-ALA-OH BOC-BETA-TBU-D-ALA-OH 112695-98-4 C12H23NO4
H-D-CYS(ACM)-OH HCL H-D-CYS(ACM)-OH HCL 200352-41-6 C6H13ClN2O3S
L-CYSTEINE-GLUTATHIONE DISULFIDE L-CYSTEINE-GLUTATHIONE DISULFIDE 13081-14-6 C13H22N4O8S2
BOC-MET-OSU BOC-MET-OSU 3845-64-5 C14H22N2O6S
PROTEIN TYROSINE PHOSPHATASE SUBSTRATE I PROTEIN TYROSINE PHOSPHATASE SUBSTRATE I 148851-08-5 C44H68N11O21P
N-LAUROYL-L-ALANINE N-LAUROYL-L-ALANINE 52558-74-4 C15H29NO3
H-BETA-ALA-NH2 HCL H-BETA-ALA-NH2 HCL 64017-81-8 C3H9ClN2O
N-ALPHA-CBZ-ARG-ARG 7-AMIDO-4-METHYLCOUMARIN HYDROCHLORIDE N-ALPHA-CBZ-ARG-ARG 7-AMIDO-4-METHYLCOUMARIN HYDROCHLORIDE 136132-67-7 C30H40ClN9O6
FMOC-D-3,4-DIMETHOXYPHENYLALANINE FMOC-D-3,4-DIMETHOXYPHENYLALANINE 218457-81-9 C26H25NO6
L-5-HYDROXYTRYPTOPHAN METHYL ESTER HYDROCHLORIDE L-5-HYDROXYTRYPTOPHAN METHYL ESTER HYDROCHLORIDE 60971-91-7 C12H15ClN2O3
L-ASPARTIC ACID MAGNESIUM SALT L-ASPARTIC ACID MAGNESIUM SALT 18962-61-3 C8H9MgN2O8-
3,5-DINITRO-L-TYROSINE SODIUM SALT 3,5-DINITRO-L-TYROSINE SODIUM SALT 502481-30-3 C9H8N3NaO7
4,4,4-TRIFLUORO-DL-VALINE 4,4,4-TRIFLUORO-DL-VALINE 16063-79-9 C5H8F3NO2
3-(Hydroxynitrosoamino)alanine 3-(Hydroxynitrosoamino)alanine 16931-22-9 C3H7N3O4
AC-HIS-OME AC-HIS-OME 36097-48-0 C9H13N3O3
BOC-(R)-3-AMINO-4-(4-TERT-BUTYL-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(4-TERT-BUTYL-PHENYL)-BUTYRIC ACID 401916-48-1 C19H29NO4
N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID N-BOC-(R)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID 288159-40-0 C10H19NO5
(2S, 4R)-4-amino-1-benzyloxycarbonyl-pyrrolidine-2-carboxylic acid-methyl ester hydrochloride (2S, 4R)-4-amino-1-benzyloxycarbonyl-pyrrolidine-2-carboxylic acid-methyl ester hydrochloride 409325-33-3 C14H19ClN2O4
N-OXALYL GLYCINE N-OXALYL GLYCINE 5262-39-5 C4H5NO5
GAMMA-GLU-CYS TRIFLUOROACETATE SALT GAMMA-GLU-CYS TRIFLUOROACETATE SALT 636-58-8 C8H14N2O5S
H-P-FLUORO-PHE-OET HCL H-P-FLUORO-PHE-OET HCL 1534-90-3 C11H15ClFNO2
D-Alanine Isopropyl Ester HCl D-Alanine Isopropyl Ester HCl 39613-92-8 C6H14ClNO2
AC-CYS(TRT)-OH AC-CYS(TRT)-OH 27486-87-9 C24H23NO3S
3-(TRIFLUOROACETYLAMINO)-1-PROPANOL 3-(TRIFLUOROACETYLAMINO)-1-PROPANOL 78008-15-8 C5H8F3NO2
AC-GLU-NH2 AC-GLU-NH2 25460-87-1 C7H12N2O4
BOC-(S)-ALPHA-(4-FLUOROBENZYL)-PROLINE BOC-(S)-ALPHA-(4-FLUOROBENZYL)-PROLINE 706806-65-7 C17H22FNO4
L-(-)-THREO-3-HYDROXYASPARTIC ACID L-(-)-THREO-3-HYDROXYASPARTIC ACID 7298-99-9 C4H7NO5
(S)-3-PHENYLALANINE T-BUTYL ESTER (S)-3-PHENYLALANINE T-BUTYL ESTER 16874-17-2 C13H19NO2
DANSYL-L-GLUTAMINE DANSYL-L-GLUTAMINE 1101-67-3 C17H21N3O5S
O-MONO-2,4-DNP-L-TYROSINE O-MONO-2,4-DNP-L-TYROSINE 10567-73-4 C15H13N3O7
(S)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID C9H10FNO2
N-[(tert-Butoxy)carbonyl]-3-methyl-L-histidine N-[(tert-Butoxy)carbonyl]-3-methyl-L-histidine 61070-22-2 C12H19N3O4
BOC-D-ARG(PBF)-OH BOC-D-ARG(PBF)-OH 186698-61-3 C24H38N4O7S
5-Amino-2,3-dihydro-1H-indene-1-carboxylic acid methyl ester 5-Amino-2,3-dihydro-1H-indene-1-carboxylic acid methyl ester 754153-28-1 C11H13NO2
5-Thiazolecarboxylicacid,2-amino-4-hydroxy-,ethylester(9CI) 5-Thiazolecarboxylicacid,2-amino-4-hydroxy-,ethylester(9CI) 72218-74-7 C6H8N2O3S
8-Oxabicyclo[3.2.1]octane-3-carboxylicacid,3-amino-,ethylester(9CI) 8-Oxabicyclo[3.2.1]octane-3-carboxylicacid,3-amino-,ethylester(9CI) 246543-68-0 C10H17NO3
1H-Pyrazole-4-carboxylicacid,5-amino-1-methyl-3-(trifluoromethyl)-(9CI) 1H-Pyrazole-4-carboxylicacid,5-amino-1-methyl-3-(trifluoromethyl)-(9CI) 317806-51-2 C6H6F3N3O2
(R)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid (R)-2-(tert-butoxycarbonylamino)-3-cyclobutylpropanoic acid 478183-61-8 C12H21NO4
Polyglutamic acid Polyglutamic acid 25513-46-6 C5H9NO4
N-Fmoc-8-Aminooctanoic acid N-Fmoc-8-Aminooctanoic acid 126631-93-4 C23H27NO4
D-LYSINE METHYL ESTER DIHYDROCHLORIDE D-LYSINE METHYL ESTER DIHYDROCHLORIDE 67396-08-1 C7H16N2O2.2HCl
cis-4-Phenylthio-L-proline hydrochloride cis-4-Phenylthio-L-proline hydrochloride 105107-84-4 C11H14ClNO2S
L-GLUTAMIC ACID GAMMA-(3-CARBOXY-4-NITROANILIDE) AMMONIUM SALT L-GLUTAMIC ACID GAMMA-(3-CARBOXY-4-NITROANILIDE) AMMONIUM SALT 63699-78-5 C12H16N4O7
BOC-GLYCINE TERT-BUTYL ESTER BOC-GLYCINE TERT-BUTYL ESTER 111652-20-1 C11H21NO4
FMOC-[15N]TYR-OH FMOC-[15N]TYR-OH 125700-34-7 C24H21NO5
N-BSMOC-GLYCINE N-BSMOC-GLYCINE 197245-13-9 C12H11NO6S
2-AMINO-5-METHYLBENZYL ALCOHOL 2-AMINO-5-METHYLBENZYL ALCOHOL 34897-84-2 C8H11NO
H-VAL-ALLYL ESTER P-TOSYLATE H-VAL-ALLYL ESTER P-TOSYLATE 88224-02-6 C15H23NO5S
3,3,3-Trifluoroalanine methyl ester hydrochloride 3,3,3-Trifluoroalanine methyl ester hydrochloride 134297-36-2 C4H7ClF3NO2
DL-3-Aminoisobutyric acid DL-3-Aminoisobutyric acid 144-90-1 C4H9NO2
AC-HIS(1-TRT)-OH AC-HIS(1-TRT)-OH 183498-47-7 C27H25N3O3
(S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID (S)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-4-AZIDOBUTANOIC ACID 942518-20-9 C19H18N4O4
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl-L-tyrosine N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-2,6-dimethyl-L-tyrosine 206060-54-0 C26H25NO5
N-Boc-cis-4-Fluoro-L-proline methyl ester N-Boc-cis-4-Fluoro-L-proline methyl ester 203866-16-4 C11H18FNO4
N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride 211914-50-0 C27H30ClN7O3
METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE 35761-27-4 C12H17ClN2O4
(4S)-4-hydroxy-L-proline hydrochloride (4S)-4-hydroxy-L-proline hydrochloride 441067-49-8 C5H10ClNO3
N-BSMOC-L-METHIONINE N-BSMOC-L-METHIONINE 197245-29-7 C15H17NO6S2
DL-N-BENZOYL-2-METHYLSERINE DL-N-BENZOYL-2-METHYLSERINE 7508-82-9 C11H13NO4
D-Thyroxine D-Thyroxine 51-49-0 C15H11I4NO4
(S)-N-(5-AMINO-1-CARBOXYPENTYL)IMINODIACETIC ACID HYDRATE (S)-N-(5-AMINO-1-CARBOXYPENTYL)IMINODIACETIC ACID HYDRATE 113231-05-3 C10H18N2O6
FMOC-ABU-OH FMOC-ABU-OH 135112-27-5 C19H19NO4
BOC-PHE-GLY-OME BOC-PHE-GLY-OME 7625-57-2 C17H24N2O5
Z-GLY-GLY-SER-OH Z-GLY-GLY-SER-OH 98352-76-2 C15H19N3O7
(2S)-1,2-PYRROLIDINEDICARBOXYLIC ACID-1-ETHYL-2-METHYL ESTER (2S)-1,2-PYRROLIDINEDICARBOXYLIC ACID-1-ETHYL-2-METHYL ESTER 93423-88-2 C9H15NO4
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