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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
Cbz-3-(2-Naphthyl)-D-alanine Cbz-3-(2-Naphthyl)-D-alanine 143218-10-4 C21H19NO4
CHLOROACETYL-GLYCYL-GLYCINE CHLOROACETYL-GLYCYL-GLYCINE 15474-96-1 C6H9ClN2O4
N-(TRIPHENYLMETHYL)GLYCINE ETHYL ESTER N-(TRIPHENYLMETHYL)GLYCINE ETHYL ESTER 18514-46-0 C23H23NO2
5-amino-1H-Indole-2-carboxylic acid ethyl ester 5-amino-1H-Indole-2-carboxylic acid ethyl ester 71086-99-2 C11H12N2O2
FMOC-(R)-3-AMINO-4-(4-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(4-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 269726-78-5 C26H22F3NO4
2,2-Diphenylglycine 2,2-Diphenylglycine 3060-50-2 C14H13NO2
FMOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 269726-72-9 C26H22F3NO4
(R)-3-AMINO-4-(2-FURYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(2-FURYL)BUTANOIC ACID HYDROCHLORIDE 270596-32-2 C8H11NO3
H-VAL-NH2 HCL H-VAL-NH2 HCL 3014-80-0 C5H12N2O.ClH
Z-D-GLN-OH Z-D-GLN-OH 13139-52-1 C13H16N2O5
2-CHLORO-L-PHENYLALANINE 2-CHLORO-L-PHENYLALANINE 185030-83-5 C9H10ClNO2
(S)-3-AMINO-4-(3-CHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-CHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 270596-38-8 C10H12ClNO2
Se-Methylselenocysteine Se-Methylselenocysteine 26046-90-2 C4H9NO2Se
BOC-(R)-3-AMINO-4-(2-FURYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-FURYL)-BUTYRIC ACID 270596-33-3 C13H19NO5
H-D-VAL-NH2 HCL H-D-VAL-NH2 HCL 133170-58-8 C5H13ClN2O
(2S,4R)-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID (2S,4R)-4-FLUORO-PYRROLIDINE-2-CARBOXYLIC ACID 2507-61-1 C5H8FNO2
N-Boc-N'-tosyl-D-histidine N-Boc-N'-tosyl-D-histidine 69541-68-0 C18H23N3O6S
(R)-3-AMINO-4-(2-CHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(2-CHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 268734-28-7 C10H12ClNO2
DL-7-Azatryptophan Monohydrate DL-7-Azatryptophan Monohydrate 7303-50-6 C10H11N3O2
BOC-D-ALA-OME BOC-D-ALA-OME 91103-47-8 C9H17NO4
(S)-3-AMINO-4-(2-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(2-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE 270065-73-1 C11H12F3NO2
(2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID (2R,4S)-N-ALPHA-T-BUTOXYCARBONYL-4-HYDROXYPYRROLIDINE-2-CARBOXYLIC ACID 147266-92-0 C10H17NO5
BOC-D-TYR(ET)-OH BOC-D-TYR(ET)-OH 76757-92-1 C16H23NO5
O-ACETYL-L-SERINE HYDROCHLORIDE O-ACETYL-L-SERINE HYDROCHLORIDE 66638-22-0 C5H10ClNO4
FMOC-(R)-3-AMINO-4-(3,4-DIFLUORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3,4-DIFLUORO-PHENYL)-BUTYRIC ACID 269396-60-3 C25H21F2NO4
(S)-3-AMINO-4-(4-BROMOPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(4-BROMOPHENYL)BUTANOIC ACID HYDROCHLORIDE 270062-84-5 C10H12BrNO2
9-Fluorenylmethyl carbamate 9-Fluorenylmethyl carbamate 84418-43-9 C15H13NO2
1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER 1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER 681807-59-0 C13H21NO4
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 103733-65-9 C10H11NO2
FMOC-ILE-OL FMOC-ILE-OL 133565-46-5 C21H25NO3
O-METHYL-D-PROLINOL O-METHYL-D-PROLINOL 84025-81-0 C6H13NO
BOC-(S)-3-AMINO-4-(4-PYRIDYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(4-PYRIDYL)-BUTYRIC ACID 219297-13-9 C14H20N2O4
Calcium L-aspartate Calcium L-aspartate 21059-46-1 C4H9CaNO4
CHLOROACETYL-L-LEUCINE CHLOROACETYL-L-LEUCINE 688-12-0 C8H14ClNO3
Z-AIB-OH Z-AIB-OH 15030-72-5 C12H15NO4
(S)-3-AMINO-4-(4-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(4-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE 270065-88-8 C11H12N2O2
N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID N-BOC-(S)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID 102507-13-1 C10H19NO5
H-DL-LEU-DL-VAL-OH H2O H-DL-LEU-DL-VAL-OH H2O 35436-83-0 C11H22N2O3
Ibuprofen lysine Ibuprofen lysine 57469-77-9 C19H32N2O4
L-LEUCINE P-NITROANILIDE HYDROCHLORIDE L-LEUCINE P-NITROANILIDE HYDROCHLORIDE 16010-98-3 C12H18ClN3O3
2-Methyl-3-amino-4-acetylanisole 2-Methyl-3-amino-4-acetylanisole 912347-94-5 C10H13NO2
[1S,2R]-trans-2-Aminocyclohexanol hydrochloride [1S,2R]-trans-2-Aminocyclohexanol hydrochloride 13374-31-7 C6H13NOHCl
D-Ornithine monohydrochloride D-Ornithine monohydrochloride 16682-12-5 C5H13ClN2O2
4-AMINO-4-PIPERIDINECARBOXYLIC ACID 4-AMINO-4-PIPERIDINECARBOXYLIC ACID 40951-39-1 C6H12N2O2
L-Aspartic acid 4-tert-butyl ester L-Aspartic acid 4-tert-butyl ester 3057-74-7 C8H15NO4
D-TYROSINE ETHYL ESTER HYDROCHLORIDE D-TYROSINE ETHYL ESTER HYDROCHLORIDE 23234-43-7 C11H16ClNO3
2-KETO-D-GLUCONIC ACID HEMICALCIUM SALT 2-KETO-D-GLUCONIC ACID HEMICALCIUM SALT 3470-37-9 C12H18CaO14
BOC-(R)-3-AMINO-4-(3,4-DICHLORO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3,4-DICHLORO-PHENYL)-BUTYRIC ACID 269396-56-7 C15H19Cl2NO4
5-AMINO-2,2-DIMETHYLPENTANOL 5-AMINO-2,2-DIMETHYLPENTANOL 13532-77-9 C7H17NO
Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate 158980-21-3 C10H11N3O2
L-Cyclobutylglycine L-Cyclobutylglycine 49607-08-1 C6H11NO2
(S)-3-AMINO-4-(3-BENZOTHIENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-BENZOTHIENYL)BUTANOIC ACID HYDROCHLORIDE 270063-44-0 C12H13NO2S
L-TYROSINE DISODIUM SALT L-TYROSINE DISODIUM SALT 122666-87-9 C9H14NNaO4
FMOC-(R)-3-AMINO-3-(4-METHYL-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(4-METHYL-PHENYL)-PROPIONIC ACID 479064-98-7 C25H23NO4
(S)-3-AMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 755749-11-2 C10H10F3NO2
(R)-3-AMINO-4-(4-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE 269726-85-4 C11H12N2O2
FMOC-(S)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID 270065-84-4 C26H22N2O4
Z-DAP(FMOC)-OH Z-DAP(FMOC)-OH 142855-80-9 C26H24N2O6
N-ACETYL-S-BENZYL-DL-CYSTEINE N-ACETYL-S-BENZYL-DL-CYSTEINE 19538-71-7 C12H15NO3S
2-Methyl-D-serine 2-Methyl-D-serine 81132-44-7 C4H9NO3
FMOC-ARG(PBF)-OPFP FMOC-ARG(PBF)-OPFP 200132-16-7 C40H39F5N4O7S
FMOC-(S)-3-AMINO-4-(2-CHLORO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-CHLORO-PHENYL)-BUTYRIC ACID 270596-37-7 C25H22ClNO4
FMOC-LYS(BOC)-OPFP FMOC-LYS(BOC)-OPFP 86060-98-2 C32H31F5N2O6
(R)-2-THIENYLGLYCINE (R)-2-THIENYLGLYCINE 65058-23-3 C6H7NO2S
L-Norvaline tert-butyl ester hydrochloride L-Norvaline tert-butyl ester hydrochloride 119483-47-5 C9H20ClNO2
BOC-3,5-DIIODO-L-TYROSINE BOC-3,5-DIIODO-L-TYROSINE 62129-53-7 C14H17I2NO5
N-(2,4-DINITROPHENYL)-L-VALINE N-(2,4-DINITROPHENYL)-L-VALINE 1694-97-9 C11H13N3O6
BOC-ALA-ONP BOC-ALA-ONP 2483-49-0 C14H18N2O6
BOC-(S)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID 270065-71-9 C15H20INO4
GLY-PRO-ARG-PRO GLY-PRO-ARG-PRO 67869-62-9 C18H31N7O5
CIS-4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID CIS-4-(BOC-AMINO)CYCLOHEXANECARBOXYLIC ACID 53292-90-3 C12H21NO4
FMOC-(R)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID 269396-54-5 C25H21Cl2NO4
L-NIO DIHYDROCHLORIDE L-NIO DIHYDROCHLORIDE 36889-13-1 C7H15N3O2
AG 490 AG 490 134036-52-5 C17H14N2O3
GLYCYL-DL-NORLEUCINE GLYCYL-DL-NORLEUCINE 1504-41-2 C8H16N2O3
Methyl 3,3,3-trifluoroalaninate Methyl 3,3,3-trifluoroalaninate 27240-44-4 C4H6F3NO2
3-Aminothiophene-2-carboxylic acid 3-Aminothiophene-2-carboxylic acid 55341-87-2 C5H5NO2S
(S)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(2-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 246876-92-6 C10H12FNO2
AC-TYR-NH2 AC-TYR-NH2 1948-71-6 C11H14N2O3
Methyl 4-aminobutyrate hydrochloride Methyl 4-aminobutyrate hydrochloride 13031-60-2 C5H12ClNO2
Z-D-GLU(OTBU)-OH Z-D-GLU(OTBU)-OH 51644-83-8 C17H23NO6
(+)-(1S,3R)-N-BOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID (+)-(1S,3R)-N-BOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID 261165-05-3 C11H19NO4
3-AMINO-2-METHYLQUINOLINE-4-CARBOXYLIC ACID 3-AMINO-2-METHYLQUINOLINE-4-CARBOXYLIC ACID 71881-80-6 C11H10N2O2
DDE-LYS(FMOC)-OH DDE-LYS(FMOC)-OH 156648-40-7 C31H36N2O6
FMOC-(S)-3-AMINO-5-PHENYLPENTANOIC ACID FMOC-(S)-3-AMINO-5-PHENYLPENTANOIC ACID 219967-74-5 C26H25NO4
N-Fmoc-N'-Boc-L-2,3-Diaminopropionic acid N-Fmoc-N'-Boc-L-2,3-Diaminopropionic acid 162558-25-0 C23H26N2O6
N-(DIPHENYLMETHYLENE)GLYCINE METHYL ESTER N-(DIPHENYLMETHYLENE)GLYCINE METHYL ESTER 81167-39-7 C16H15NO2
BOC-DL-PHE-OH BOC-DL-PHE-OH 4530-18-1 C14H19NO4
FMOC-(S)-3-AMINO-4-(3-FLUORO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(3-FLUORO-PHENYL)-BUTYRIC ACID 270596-52-6 C25H22FNO4
BOC-3,4-DEHYDRO-PRO-OH BOC-3,4-DEHYDRO-PRO-OH 51154-06-4 C10H15NO4
N-Carbobenzyloxy-L-threonine methyl ester N-Carbobenzyloxy-L-threonine methyl ester 57224-63-2 C13H17NO5
FMOC-(R)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(2-CYANO-PHENYL)-BUTYRIC ACID 269726-81-0 C26H22N2O4
AG 1478 AG 1478 175178-82-2 C16H14ClN3O2
BETA-(2-PYRIDYL)-DL-ALANINE BETA-(2-PYRIDYL)-DL-ALANINE 17407-39-5 C8H10N2O2
FMOC-CYS(ACM)-OPFP FMOC-CYS(ACM)-OPFP 86060-96-0 C27H21F5N2O5S
PROTEASOME INHIBITOR I PROTEASOME INHIBITOR I 158442-41-2 C32H50N4O8
3-AMINOTETRAHYDROFURAN-3-CARBOXYLIC ACID 3-AMINOTETRAHYDROFURAN-3-CARBOXYLIC ACID 125218-55-5 C5H9NO3
N-Methyl-L-aspartic acid N-Methyl-L-aspartic acid 4226-18-0 C5H9NO4
BOC-D-ARG-OH HCL H2O BOC-D-ARG-OH HCL H2O 113712-06-4 C11H23ClN4O4
Z-ALA-OSU Z-ALA-OSU 3401-36-3 C15H16N2O6
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