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
FMOC-TYR(2-BR-Z)-OH FMOC-TYR(2-BR-Z)-OH 147688-40-2 C32H26BrNO7
Potassium (R)-((3-ethoxy-1-methyl-3-oxoprop-1-enyl)amino)(4-hydroxyphenyl)acetate Potassium (R)-((3-ethoxy-1-methyl-3-oxoprop-1-enyl)amino)(4-hydroxyphenyl)acetate 57938-86-0 C14H16KNO5
2,4-Difluoro-D-phenylalanine 2,4-Difluoro-D-phenylalanine 266360-60-5 C9H9F2NO2
N-ACETYL-S-GERANYLGERANYL-L-CYSTEINE N-ACETYL-S-GERANYLGERANYL-L-CYSTEINE 139332-94-8 C25H41NO3S
BOC-L-BETA-HOMOVALINE BOC-L-BETA-HOMOVALINE 183990-64-9 C11H21NO4
5-Benzothiazolecarboxylicacid,2-amino- 5-Benzothiazolecarboxylicacid,2-amino- 101084-95-1 C8H6N2O2S
N-α-Z-N-β-Boc-D-2,3-diaminopropionic acid N-α-Z-N-β-Boc-D-2,3-diaminopropionic acid 62234-36-0 C16H22N2O6
(R)-3-AMINO-4-(3-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(3-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 331763-65-6 C10H13ClFNO2
(S)-(+)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLGLYCINE (S)-(+)-N-(3,5-DINITROBENZOYL)-ALPHA-PHENYLGLYCINE 90761-62-9 C15H11N3O7
AC-DMQD-CHO AC-DMQD-CHO 259199-63-8 C20H31N5O10S
FA-GLY-OH FA-GLY-OH 124882-74-2 C9H9NO4
D-2,4-Diaminobutyric acid D-2,4-Diaminobutyric acid 26908-94-1 C4H10N2O2
1H-Pyrazole-3-carboxylicacid,5-amino-,methylester(9CI) 1H-Pyrazole-3-carboxylicacid,5-amino-,methylester(9CI) 632365-54-9 C5H7N3O2
Boc-S-trityl-D-cysteine Boc-S-trityl-D-cysteine 87494-13-1 C27H29NO4S
L-Glutamic acid α-tert·butyl ester L-Glutamic acid α-tert·butyl ester 45120-30-7 C9H17NO4
N-im-Trityl-D-histidine N-im-Trityl-D-histidine 199119-46-5 C25H23N3O2
FMOC-D-THR-OH FMOC-D-THR-OH 157355-81-2 C19H19NO5
BOC-D-ASP(OTBU)-OH DCHA BOC-D-ASP(OTBU)-OH DCHA 200334-95-8 C25H46N2O6
N-Cbz-N-methyl-L-isoleucine N-Cbz-N-methyl-L-isoleucine 42417-66-3 C15H21NO4
FMOC-HOMOSER(TRT)-OH FMOC-HOMOSER(TRT)-OH 111061-55-3 C38H33NO5
D-P-METHYL SULFONE PHENYL ETHYL SERINATE D-P-METHYL SULFONE PHENYL ETHYL SERINATE 36983-12-7 C12H17NO5S
H-D-VAL-OET HCL H-D-VAL-OET HCL 73913-64-1 C7H16ClNO2
BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID BUTOXYCARBONYLAMINO-CYCLOPROPYL-ACETIC ACID 54256-41-6 C10H17NO4
Z-GLU-TYR-OH Z-GLU-TYR-OH 988-75-0 C22H24N2O8
FMOC-D-CYCLOPROPYLALANINE FMOC-D-CYCLOPROPYLALANINE 170642-29-2 C21H21NO4
N-ACETYL-S-BENZYL-L-CYSTEINE N-ACETYL-S-BENZYL-L-CYSTEINE 19542-77-9 C12H15NO3S
BETA-CHLORO-D-ALANINE HYDROCHLORIDE BETA-CHLORO-D-ALANINE HYDROCHLORIDE 17136-54-8 C4H8ClNO2.ClH
AC-THR-OH AC-THR-OH 17093-74-2 C6H11NO4
(S)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID C9H10ClNO2
BETA-T-BUTYL-D-ALANINE BETA-T-BUTYL-D-ALANINE 88319-43-1 C7H15NO2
(2S,3R,4S)-CCG (2S,3R,4S)-CCG 117857-95-1 C6H9NO4
(S)-3-AMINO-3-(4-METHYL-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(4-METHYL-PHENYL)-PROPIONIC ACID C10H13NO2
BOC-D-TYR-OME BOC-D-TYR-OME 76757-90-9 C15H21NO5
Fmoc-(S)-3-Amino-3-phenylpropionic acid Fmoc-(S)-3-Amino-3-phenylpropionic acid 209252-15-3 C24H21NO4
DL-ISOSERINE DL-ISOSERINE 632-12-2 C3H7NO3
BOC-(S)-3-AMINO-3-(3-HYDROXY-PHENYL)-PROPIONIC ACID BOC-(S)-3-AMINO-3-(3-HYDROXY-PHENYL)-PROPIONIC ACID 499995-79-8 C14H19NO5
DABSYL-L-METHIONINE DABSYL-L-METHIONINE 97684-99-6 C19H24N4O4S2
METHYL 3-AMINOTHIENO[3,2-B]PYRIDINE-2-CARBOXYLATE METHYL 3-AMINOTHIENO[3,2-B]PYRIDINE-2-CARBOXYLATE 111042-90-1 C9H8N2O2S
GLYCYL-D-SERINE GLYCYL-D-SERINE 82660-87-5 C5H10N2O4
FMOC-ALA-OH H2O FMOC-ALA-OH H2O C18H19NO5
BOC-DL-MET-OH BOC-DL-MET-OH 93000-03-4 C10H19NO4S
N-BOC-4,4-difluoro-L-proline N-BOC-4,4-difluoro-L-proline 203866-15-3 C10H15F2NO4
2-Chloropropionylglycine 2-Chloropropionylglycine 85038-45-5 C5H8ClNO3
3-(2-Furyl)-D-alanine 3-(2-Furyl)-D-alanine C7H9NO3
2,5-Difluoro-D-phenylalanine 2,5-Difluoro-D-phenylalanine 266360-61-6 C9H9F2NO2
FMOC-PRO-OPFP FMOC-PRO-OPFP 125281-38-1 C26H18F5NO4
(R)-3-(P-METHYLPHENYL)-BETA-ALANINE
(R)-3-(P-METHYLPHENYL)-BETA-ALANINE 479064-87-4 C10H13NO2
(R)-3-AMINO-4-PENTAFLUOROPHENYLBUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-PENTAFLUOROPHENYLBUTANOIC ACID HYDROCHLORIDE 269398-92-7 C10H8F5NO2
N-L-gamma-Glutamyl-L-leucine N-L-gamma-Glutamyl-L-leucine 2566-39-4 C11H20N2O5
FMOC-L-STYRYLALANINE FMOC-L-STYRYLALANINE 159610-82-9 C26H23NO4
N-(TERT-BUTOXYCARBONYL)-3-(4-(1-PYRROLYL)PHENYL)-L-ALANINE N-(TERT-BUTOXYCARBONYL)-3-(4-(1-PYRROLYL)PHENYL)-L-ALANINE 312619-46-8 C18H22N2O4
FMOC-(R)-3-AMINO-4-(3-FLUORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3-FLUORO-PHENYL)-BUTYRIC ACID 331763-67-8 C25H22FNO4
N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER N-BOC-TRANS-4-HYDROXY-D-PROLINE METHYL ESTER 135042-17-0 C11H19NO5
N-Carbobenzoxy-L-homoserine N-Carbobenzoxy-L-homoserine 35677-88-4 C12H15NO5
BOC-D-2,4-DICHLOROPHENYLALANINE BOC-D-2,4-DICHLOROPHENYLALANINE 114873-12-0 C14H17Cl2NO4
BOC-CHA-OH DCHA BOC-CHA-OH DCHA 37462-62-7 C26H48N2O4
GLYCYL-D-THREONINE DIHYDRATE GLYCYL-D-THREONINE DIHYDRATE 74807-44-6 C6H16N2O6
(R)-N-BOC-4-FLUOROPHENYLGLYCINE (R)-N-BOC-4-FLUOROPHENYLGLYCINE 196707-32-1 C13H16FNO4
Methyl 1-Aminocyclopropanecarboxylate Methyl 1-Aminocyclopropanecarboxylate 72784-43-1 C5H9NO2
DIMETHYL DL-GLUTAMATE HYDROCHLORIDE DIMETHYL DL-GLUTAMATE HYDROCHLORIDE 13515-99-6 C7H14ClNO4
FMOC-(R)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID 331763-60-1 C25H22ClNO4
N-Benzyloxycarbonyl-L-lysinyl-L-proline N-Benzyloxycarbonyl-L-lysinyl-L-proline 42001-60-5 C19H27N3O5
(R)-3-AMINO-4-(4-BROMOPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-BROMOPHENYL)BUTANOIC ACID HYDROCHLORIDE 331763-73-6 C10H13BrClNO2
SUC-ALA-ALA-ALA-PNA SUC-ALA-ALA-ALA-PNA 52299-14-6 C19H25N5O8
L-ALPHA-PHOSPHATIDYL-L-SERINE L-ALPHA-PHOSPHATIDYL-L-SERINE C42H82NO10P
BOC-4,5-DEHYDRO-LEU-OH DCHA BOC-4,5-DEHYDRO-LEU-OH DCHA 87720-54-5 C23H42N2O4
H-PHE-ALA-OH H-PHE-ALA-OH 3918-87-4 C12H16N2O3
H-L-MEGLU-OH HCL H-L-MEGLU-OH HCL 6753-62-4 C6H11NO4
FMOC-D-GLU-OTBU FMOC-D-GLU-OTBU 109745-15-5 C24H27NO6
H-D-CHG-OH HCL H-D-CHG-OH HCL 61367-40-6 C8H16ClNO2
N-(2-PYRIDYLMETHYL)GLYCINE ETHYL ESTER N-(2-PYRIDYLMETHYL)GLYCINE ETHYL ESTER 62402-24-8 C10H14N2O2
ELASTATINAL ELASTATINAL 51798-45-9 C21H36N8O7
FMOC-HSE(ME)-OH FMOC-HSE(ME)-OH 173212-86-7 C20H21NO5
DL-2,3-DIFLUOROPHENYLALANINE DL-2,3-DIFLUOROPHENYLALANINE 236754-62-4 C9H9F2NO2
FMOC-DAB(Z)-OH FMOC-DAB(Z)-OH 252049-08-4 C27H26N2O6
DL-Ornithine hydrochloride DL-Ornithine hydrochloride 1069-31-4 C5H13ClN2O2
FMOC-L-CYCLOPENTYLGLYCINE FMOC-L-CYCLOPENTYLGLYCINE 220497-61-0 C22H23NO4
AC-GLU(OTBU)-OH AC-GLU(OTBU)-OH 84192-88-1 C11H19NO5
(S)-3-AMINO-3-(2-CHLORO-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(2-CHLORO-PHENYL)-PROPIONIC ACID C9H10ClNO2
FMOC-(R)-3-AMINO-4-(3-PYRIDYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3-PYRIDYL)-BUTYRIC ACID 269396-66-9 C24H22N2O4
N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER N-BOC-TRANS-4-CYANO-L-PROLINE METHYL ESTER 194163-91-2 C12H18N2O4
H-PRO-PNA TFA H-PRO-PNA TFA 108321-19-3 C13H14F3N3O5
DL-VALINE ETHYL ESTER HYDROCHLORIDE DL-VALINE ETHYL ESTER HYDROCHLORIDE 23358-42-1 C7H16ClNO2
FMOC-(R)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID 331763-57-6 C25H22ClNO4
FMOC-GLY-OSU FMOC-GLY-OSU 113484-74-5 C21H18N2O6
BIS(2,4-DINITROPHENYL)-L-HISTIDINE BIS(2,4-DINITROPHENYL)-L-HISTIDINE 3129-33-7 C18H13N7O10
PYRIDOXYLIDENE-L-ISOLEUCINE POTASSIUM SALT PYRIDOXYLIDENE-L-ISOLEUCINE POTASSIUM SALT 57212-58-5 C14H20N2O4
BOC-D-2-AMINO-5-PHENYL-PENTANOIC ACID DCHA SALT BOC-D-2-AMINO-5-PHENYL-PENTANOIC ACID DCHA SALT 156130-68-6 C16H23NO4
BOC-MET(O2)-OH BOC-MET(O2)-OH 60280-45-7 C10H19NO6S
Z-ARG(PMC)-OH CHA Z-ARG(PMC)-OH CHA 112160-33-5 C34H51N5O7S
DL-TRYPTOPHAN ETHYL ESTER HYDROCHLORIDE DL-TRYPTOPHAN ETHYL ESTER HYDROCHLORIDE C13H17ClN2O2
6-(FMOC-AMINO)-1-HEXANOL 6-(FMOC-AMINO)-1-HEXANOL 127903-20-2 C21H25NO3
N-CARBOBENZOXY-4-OXO-L-PROLINE N-CARBOBENZOXY-4-OXO-L-PROLINE 64187-47-9 C13H13NO5
H-GLU(AMC)-OH H-GLU(AMC)-OH 72669-53-5 C15H16N2O5
BETA-ASPARTAME BETA-ASPARTAME 22839-61-8 C14H18N2O5
BOC-AZA-L-LEUCINE BOC-AZA-L-LEUCINE 94778-71-9 C10H20N2O4
FMOC-(S)-3-AMINO-3-(3-HYDROXY-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(3-HYDROXY-PHENYL)-PROPIONIC ACID 501015-32-3 C24H21NO5
(R)-N-BOC-5-METHOXYCARBONYL-2-PYRROLIDINONE (R)-N-BOC-5-METHOXYCARBONYL-2-PYRROLIDINONE 128811-48-3 C11H17NO5
(R)-3-Amino-3-(2-(trifluoromethyl)phenyl)propanoic acid (R)-3-Amino-3-(2-(trifluoromethyl)phenyl)propanoic acid 791582-16-6 C10H10F3NO2
S-BENZYL-L-CYSTEINOL S-BENZYL-L-CYSTEINOL 85803-43-6 C10H15NOS
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