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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
ON-01910 ON-01910 1225497-78-8 C21H26NNaO8S
(S)-ethyl 2-propionamidopropanoate (S)-ethyl 2-propionamidopropanoate 42167-52-2 C8H15NO3
tert-Butyl (2R)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate tert-Butyl (2R)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate 128811-37-0 C10H17NO4
(1-ADAMANTANEACETYL-D-ARG0,HYP3,BETA-(2-THIENYL)-ALA5,8,D-PHE7)-BRADYKININ (1-ADAMANTANEACETYL-D-ARG0,HYP3,BETA-(2-THIENYL)-ALA5,8,D-PHE7)-BRADYKININ 130942-96-0 C68H99N19O14S2
BOC-S-TERT-BUTYLMERCAPTO-L-CYSTEINE BOC-S-TERT-BUTYLMERCAPTO-L-CYSTEINE 30044-61-2 C12H23NO4S2
TOS-ALA-OH TOS-ALA-OH 99076-56-9 C10H13NO4S
BZ-PHE-NH2 BZ-PHE-NH2 72150-35-7 C16H16N2O2
(R)-(+)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL (R)-(+)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL 86906-05-0 C21H21NO
(S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL (S)-(-)-2-AMINO-1,1,3-TRIPHENYL-1-PROPANOL 79868-78-3 C21H21NO
L-4-THIAZOLYLALANINE L-4-THIAZOLYLALANINE 136010-41-8 C6H8N2O2S
ALPHA-METHYL-DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE ALPHA-METHYL-DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE 64665-60-7 C11H16ClNO2
3-METHYLAMINO-BENZOIC ACID 3-METHYLAMINO-BENZOIC ACID 51524-84-6 C8H9NO2
N-ACETYL-S-(3-HYDROXYPROPYL-1-METHYL)-L-CYSTEINE, DICYCLOHEXYLAMMONIUM SALT N-ACETYL-S-(3-HYDROXYPROPYL-1-METHYL)-L-CYSTEINE, DICYCLOHEXYLAMMONIUM SALT 33164-70-4 C21H40N2O4S
H-DL-ASP-OME H-DL-ASP-OME 65414-77-9 C5H9NO4
FMOC-(R)-2-THIENYLGLYCINE FMOC-(R)-2-THIENYLGLYCINE 208259-66-9 C21H17NO4S
H-PRO-4M-BETANA HCL H-PRO-4M-BETANA HCL 100930-07-2 C16H19ClN2O2
BOC-(R)-3-AMINO-3-(3-BROMO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(3-BROMO-PHENYL)-PROPIONIC ACID C14H18BrNO4
(2S, 4R)-BOC-GAMMA-MSO-PROLINE METHYL ESTER (2S, 4R)-BOC-GAMMA-MSO-PROLINE METHYL ESTER 84520-67-2 C12H21NO7S
ARG-LYS-GLU-VAL-TYR ACETATE SALT ARG-LYS-GLU-VAL-TYR ACETATE SALT 105184-37-0 C33H55N9O11
FMOC-ALA(BETA-CYCLOBUTYL)-OH FMOC-ALA(BETA-CYCLOBUTYL)-OH 478183-62-9 C22H23NO4
FMOC-D-CIT-OH FMOC-D-CIT-OH 200344-33-8 C21H23N3O5
5-METHYL-DL-TRYPTOPHAN 5-METHYL-DL-TRYPTOPHAN 951-55-3 C12H14N2O2
FMOC-[15N]VAL-OH FMOC-[15N]VAL-OH 125700-35-8 C20H21NO4
Z-D-CIS-HYP-OH Z-D-CIS-HYP-OH 130930-25-5 C13H15NO5
MEOSUC-AAPM-PNA MEOSUC-AAPM-PNA 70967-91-8 C27H38N6O9S
L-Leucine hydrochloride L-Leucine hydrochloride 760-84-9 C6H14ClNO2
N-Hexadecanoyl-L-valine N-Hexadecanoyl-L-valine 45287-42-1 C21H41NO3
Sodium N-tetradecanoyl-L-phenlyalaninate Sodium N-tetradecanoyl-L-phenlyalaninate 36577-41-0 C23H36NNaO3
N-Palmitoyl-L-serine N-Palmitoyl-L-serine 16417-38-2 C19H37NO4
DL-2-ISOPROPYLSERINE DL-2-ISOPROPYLSERINE 7522-43-2 C6H13NO3
H-TYR-AMC TFA H-TYR-AMC TFA 94099-57-7 C19H18N2O4
N-BENZOYL-L-THREONINE N-BENZOYL-L-THREONINE 27696-01-1 C11H13NO4
N-BSMOC-L-ASPARAGINE N-BSMOC-L-ASPARAGINE 197245-31-1 C14H14N2O7S
BOC-(S)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID BOC-(S)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID C15H21NO4
Z-ASP-OME DCHA Z-ASP-OME DCHA 19720-12-8 C25H38N2O6
BENZOYLGLYCINE METHYL ESTER BENZOYLGLYCINE METHYL ESTER 1205-08-9 C10H11NO3
N-Formyl-L-aspartic acid N-Formyl-L-aspartic acid 19427-28-2 C5H7NO5
(BOC-CYS-OH)2 (BOC-CYS-OH)2 10389-65-8 C16H28N2O8S2
CBZL-D-TERT-LEUCINE CBZL-D-TERT-LEUCINE 70874-05-4 C14H19NO4
DL-2-BENZYLSERINE DL-2-BENZYLSERINE 4740-47-0 C10H13NO3
L-GLUTAMIC-15N ACID L-GLUTAMIC-15N ACID 21160-87-2 C5H9NO4
ARG-ARG BETA-NAPHTHYLAMIDE TRIHYDROCHLORIDE ARG-ARG BETA-NAPHTHYLAMIDE TRIHYDROCHLORIDE 100900-26-3 C22H36Cl3N9O2
Ademethionine 1,4-Butanedisulfonate Ademethionine 1,4-Butanedisulfonate 101020-79-5 C42H74N12O28S8
methyl 3-phenyl-L-alaninate methyl 3-phenyl-L-alaninate 2577-90-4 C10H13NO2
L-Cyclopentyl-gly-methyl ester HCL L-Cyclopentyl-gly-methyl ester HCL 14328-62-2 C8H16ClNO2
3,4,5-Trifluoro-L-phenylalanine 3,4,5-Trifluoro-L-phenylalanine 646066-73-1 C9H8F3NO2
DL-2-Cyanophenylalanine DL-2-Cyanophenylalanine 263396-40-3 C10H10N2O2
3,4-Difluorophenylglycine 3,4-Difluorophenylglycine 225641-94-1 C8H7F2NO2
2-Bromo-DL-Phenylalanine 2-Bromo-DL-Phenylalanine 30163-16-7 C9H10BrNO2
(R)-2-Amino-3-(4-ethylphenyl)propanoic acid (R)-2-Amino-3-(4-ethylphenyl)propanoic acid 721385-17-7 C11H15NO2
(S)-(-)-(3-CHLORO-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE (S)-(-)-(3-CHLORO-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE 101396-91-2 C6H15Cl2NO
(1S,2R)-2-Aminocyclopentanecarboxylic acid (1S,2R)-2-Aminocyclopentanecarboxylic acid 64191-14-6 C6H11NO2
Benzoic acid, 3-amino-4,5-dichloro- (9CI) Benzoic acid, 3-amino-4,5-dichloro- (9CI) 50917-30-1 C7H5Cl2NO2
FMOC-(R)-3-AMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 517905-86-1 C25H20F3NO4
METHYL (3S)-3-AMINO-3-PHENYLPROPANOATE METHYL (3S)-3-AMINO-3-PHENYLPROPANOATE 37088-66-7 C10H13NO2
Citiolone Citiolone 17896-21-8 C6H9NO2S
N-ACETYL-5-METHOXY-DL-TRYPTOPHAN MONOHYDRATE N-ACETYL-5-METHOXY-DL-TRYPTOPHAN MONOHYDRATE 43167-40-4 C14H16N2O4
BOC-TYR-OBZL BOC-TYR-OBZL 19391-35-6 C21H25NO5
POLY(GLU, TYR) SODIUM SALT POLY(GLU, TYR) SODIUM SALT 97105-00-5 C14H21N2NaO7
3-NITRO-L-TYROSINE ETHYL ESTER HYDROCHLORIDE 3-NITRO-L-TYROSINE ETHYL ESTER HYDROCHLORIDE 66737-54-0 C11H15ClN2O5
BZ-MET-NH2 BZ-MET-NH2 52811-71-9 C12H16N2O2S
N-DICHLOROACETYL-L-SERINE SODIUM SALT N-DICHLOROACETYL-L-SERINE SODIUM SALT 80174-64-7 C5H7Cl2NO4
FMOC-L-PHE(4-GUANIDINO-BOC2)-OH FMOC-L-PHE(4-GUANIDINO-BOC2)-OH 187283-25-6 C35H40N4O8
BOC-ALPHA-ALLYL-ME-DL-PRO-OH BOC-ALPHA-ALLYL-ME-DL-PRO-OH 203869-80-1 C11H19NO4
(1R,2R)-2-AMINO-1,2-DIPHENYLETHANOL, 97 (1R,2R)-2-AMINO-1,2-DIPHENYLETHANOL, 97 88082-66-0 C14H15NO
Z-D-PROLINOL, 97 Z-D-PROLINOL, 97 72597-18-3 C13H17NO3
L-GLUTAMIC ACID MONOPOTASSIUM SALT L-GLUTAMIC ACID MONOPOTASSIUM SALT 6382-01-0 C5H8NO4.K.H2O
N-Tetradecanoyl-L-alanine N-Tetradecanoyl-L-alanine 71448-29-8 C17H33NO3
N-Dodecanoyl-L-proline N-Dodecanoyl-L-proline 58725-39-6 C17H31NO3
3,3,3-TRIFLUORO-DL-ALANINE 3,3,3-TRIFLUORO-DL-ALANINE 10065-69-7 C3H4F3NO2
H-DL-PHE(4-CN)-OH H-DL-PHE(4-CN)-OH C10H10N2O2
N-FMOC-3-(triphenylmethyl)-L-histidine N-FMOC-3-(triphenylmethyl)-L-histidine 128545-09-5 C40H33N3O4
1H-Thieno[3,2-c]pyrazole-5-carboxylic acid, 3-amino-, methyl ester 1H-Thieno[3,2-c]pyrazole-5-carboxylic acid, 3-amino-, methyl ester 648411-35-2 C7H7N3O2S
2,4-Dichloro-DL-phenylalanine 2,4-Dichloro-DL-phenylalanine 5472-68-4 C9H9Cl2NO2
(R)-3-Amino-3-(2-bromo-phenyl)-propionic acid (R)-3-Amino-3-(2-bromo-phenyl)-propionic acid 737751-95-0 C9H10BrNO2
(S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE
(S)-N-BOC-(2'-CHLOROPHENYL)GLYCINE 225918-60-5 C13H16ClNO4
H-[15N]LEU-OH H-[15N]LEU-OH 59935-31-8 C6H13NO2
Z-ASP(OTBU)-OH DCHA Z-ASP(OTBU)-OH DCHA 23632-70-4 C28H44N2O6
EDTA DIPOTASSIUM MAGNESIUM SALT, DIHYDRATE EDTA DIPOTASSIUM MAGNESIUM SALT, DIHYDRATE 68015-77-0 C10H16K2MgN2O10
H-D-ALA-GLY-OH H-D-ALA-GLY-OH 3997-90-8 C5H10N2O3
S-2-Hydroxyethyl-D-cysteine S-2-Hydroxyethyl-D-cysteine 85955-36-8 C5H11NO3S
Ethyl 1-Boc-4-iso-propyl-4-piperidinecarboxylate Ethyl 1-Boc-4-iso-propyl-4-piperidinecarboxylate 1022128-75-1 C16H29NO4
FMOC-THR(TBU)-ODHBT FMOC-THR(TBU)-ODHBT 119767-84-9 C30H30N4O6
H-D-Glu(Otbu)-OMe.HCL H-D-Glu(Otbu)-OMe.HCL 16948-36-0 C10H19NO4.ClH
3-Amino-N-Boc-L-alanine methyl ester 3-Amino-N-Boc-L-alanine methyl ester 61040-20-8 C9H18N2O4
H-CYS(BZL)-OET HCL H-CYS(BZL)-OET HCL 52844-67-4 C12H18ClNO2S
ALPHA-METHYL-DL-SERINE ALPHA-METHYL-DL-SERINE 3398-40-1 C4H9NO3
FMOC-MENVA-OH FMOC-MENVA-OH 252049-05-1 C21H23NO4
(S)-(+)-1-DIMETHYLAMINO-2-PROPANOL (S)-(+)-1-DIMETHYLAMINO-2-PROPANOL 53636-17-2 C5H13NO
Fmoc-S-Trityl-L-penicillamine Fmoc-S-Trityl-L-penicillamine 201531-88-6 C39H35NO4S
L-4-TRIFLUOROMETHYLPHENYLALANINE L-4-TRIFLUOROMETHYLPHENYLALANINE 122839-56-9 C10H10F3NO2
FMOC-HOCHA-OH FMOC-HOCHA-OH 269078-73-1 C25H29NO4
L-GLUTAMINE-15N2 L-GLUTAMINE-15N2 204451-48-9 C5H10N2O3
FMOC-GLU-OBZL FMOC-GLU-OBZL 122350-52-1 C27H25NO6
N-CARBOBENZYLOXY-L-PROLINE METHYL ESTER N-CARBOBENZYLOXY-L-PROLINE METHYL ESTER 5211-23-4 C14H17NO4
N-FORMYLGLYCINE METHYL ESTER N-FORMYLGLYCINE METHYL ESTER 3154-54-9 C4H7NO3
GLYCINE N-BUTYL ESTER HYDROCHLORIDE GLYCINE N-BUTYL ESTER HYDROCHLORIDE 13048-99-2 C6H14ClNO2
BOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID C14H18FNO4
FA-GLY-LEU-NH2 FA-GLY-LEU-NH2 26400-33-9 C15H21N3O4
1-(FMOC-AMINO)CYCLOHEXANECARBOXYLIC ACID 1-(FMOC-AMINO)CYCLOHEXANECARBOXYLIC ACID 162648-54-6 C22H23NO4
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