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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
N-Hexadecanoyl-L-alanine N-Hexadecanoyl-L-alanine 56255-31-3 C19H37NO3
Sodium N-hexadecanoyl-L-phenlyalaninate Sodium N-hexadecanoyl-L-phenlyalaninate 32190-55-9 C25H40NNaO3
FOR-ASP-PHE-OME FOR-ASP-PHE-OME 33605-76-4 C15H18N2O6
BOC-VAL-PRO-ARG-AMC HCL BOC-VAL-PRO-ARG-AMC HCL 70375-24-5 C31H46ClN7O7
FMOC-L-PHENYLALANYL CHLORIDE FMOC-L-PHENYLALANYL CHLORIDE 103321-57-9 C24H20ClNO3
(S)-AMINO-(2-METHOXY-PHENYL)-ACETIC ACID (S)-AMINO-(2-METHOXY-PHENYL)-ACETIC ACID 103889-86-7 C9H11NO3
1-BOC-4-ETHYL-4-PIPERIDINECARBOXYLIC ACID 1-BOC-4-ETHYL-4-PIPERIDINECARBOXYLIC ACID 188792-67-8 C13H23NO4
BOC-BETA-(2-QUINOLYL)-ALA-OH BOC-BETA-(2-QUINOLYL)-ALA-OH 161453-37-8 C17H20N2O4
CBZ-GLY HYDRAZIDE CBZ-GLY HYDRAZIDE 5680-83-1 C10H13N3O3
FMOC-ASN-OPFP FMOC-ASN-OPFP 86060-99-3 C25H17F5N2O5
FMOC-N-ME-ARG(MTR)-OH FMOC-N-ME-ARG(MTR)-OH 214750-72-8 C32H38N4O7S
DL-ALANYL-DL-NORVALINE DL-ALANYL-DL-NORVALINE 2325-18-0 C8H16N2O3
N-Benzyloxycarbonyl-L-lysine benzyl ester p-toluenesulfonate N-Benzyloxycarbonyl-L-lysine benzyl ester p-toluenesulfonate 16964-83-3 C28H34N2O7S
(R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid (R)-2-Acetamido-3-(4-nitrophenyl)propanoic acid 89615-73-6 C11H12N2O5
2,3,4,5-Tetrafluoro-D-Phenylalanine 2,3,4,5-Tetrafluoro-D-Phenylalanine 747405-49-8 C9H7F4NO2
S-(acetamidomethyl)-L-cysteine S-(acetamidomethyl)-L-cysteine 19647-70-2 C6H12N2O3S
(S)-3-(3-CHLOROPHENYL)-BETA-ALANINE
(S)-3-(3-CHLOROPHENYL)-BETA-ALANINE 774178-18-6 C9H10ClNO2
(R)-3-(3-FLUOROPHENYL)-BETA-ALANINE
(R)-3-(3-FLUOROPHENYL)-BETA-ALANINE 723284-81-9 C9H10FNO2
BOC-D-NVA-OH BOC-D-NVA-OH 57521-85-4 C10H19NO4
CIS-2-AMINO-4-CYCLOHEXENE-1-CARBOXYLIC ACID CIS-2-AMINO-4-CYCLOHEXENE-1-CARBOXYLIC ACID 54162-90-2 C7H11NO2
Ketoprofen lysinate Ketoprofen lysinate 57469-78-0 C22H28N2O5
L-TYROSINE ETHYL ESTER HYDROCHLORIDE L-TYROSINE ETHYL ESTER HYDROCHLORIDE 34081-17-9 C11H15NO3
METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE METHYL 4-HYDROXY-1-[(4-METHYLPHENYL)SULFONYL]-2-PYRROLIDINECARBOXYLATE 16257-57-1 C13H17NO5S
(1S,2S)-(+)-2-AMINO-3-METHOXY-1-PHENYL-1-PROPANOL (1S,2S)-(+)-2-AMINO-3-METHOXY-1-PHENYL-1-PROPANOL 51594-34-4 C10H15NO2
H-D-Asp(OtBu)-OtBu · HCl H-D-Asp(OtBu)-OtBu · HCl 135904-71-1 C12H23NO4.HCl
N-CARBOBENZOXY-D-LEUCINE DICYCLOHEXYLAMMONIUM SALT N-CARBOBENZOXY-D-LEUCINE DICYCLOHEXYLAMMONIUM SALT 7662-58-0 C14H19NO4.C12H23N
FMOC-GLU(ODMAB)-OH FMOC-GLU(ODMAB)-OH 172611-75-5 C40H44N2O8
5-Benzyl L-glutamate N-carboxyanhydride 5-Benzyl L-glutamate N-carboxyanhydride 3190-71-4 C13H13NO5
BOC-L-PYROGLUTAMIC ACID BENZYL ESTER BOC-L-PYROGLUTAMIC ACID BENZYL ESTER 113400-36-5 C17H21NO5
N-BSMOC-L-VALINE N-BSMOC-L-VALINE 197245-17-3 C15H17NO6S
BOC-D-2-AMINOSUBERIC ACID BOC-D-2-AMINOSUBERIC ACID 75113-71-2 C13H23NO6
(2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride (2S,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride 481704-21-6 C6H12ClNO3
(R)-TERT-LEUCINOL (R)-TERT-LEUCINOL 112245-09-7 C6H15NO
2-AMINO-2-METHYLSUCCINIC ACID 2-AMINO-2-METHYLSUCCINIC ACID 2792-66-7 C5H9NO4
TOS-PRO-OH TOS-PRO-OH 51077-01-1 C12H15NO4S
H-ASP-ASP-ASP-ASP-OH H-ASP-ASP-ASP-ASP-OH 145224-95-9 C16H22N4O13
FMOC-D-ARG(BOC)2-OH FMOC-D-ARG(BOC)2-OH 214852-34-3 C31H40N4O8
L-VALINE, N-[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]-, METHYL ESTER, MONOHYDROCHLORIDE L-VALINE, N-[(2'-CYANO[1,1'-BIPHENYL]-4-YL)METHYL]-, METHYL ESTER, MONOHYDROCHLORIDE 482577-59-3 C20H23ClN2O2
H-D-LYS(BOC)-OTBU HCL H-D-LYS(BOC)-OTBU HCL 201007-86-5 C15H31ClN2O4
BETA-(2-THIENYL)-DL-SERINE BETA-(2-THIENYL)-DL-SERINE 32595-59-8 C7H9NO3S
FDNP-VAL-NH2 FDNP-VAL-NH2 132679-61-9 C11H13FN4O5
L-Cyclobutylalanine L-Cyclobutylalanine C7H13NO2
N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester N-((N-Methyl-N-((2-isopropyl-4-thiazolyl)methyl)amino)carbonyl)-L-valine methyl ester 154248-99-4 C15H25N3O3S
S-Allyl-D-cysteine S-Allyl-D-cysteine 770742-93-3 C6H11NO2S
H-LYS(ALLOC)-OH H-LYS(ALLOC)-OH 6298-03-9 C10H18N2O4
D-S-tert-Butylcysteine D-S-tert-Butylcysteine 2481-10-9 C7H15NO2S
3-(N-Ethanolamino)-L-alanine 3-(N-Ethanolamino)-L-alanine 848396-10-1 C6H9N3O2
(R)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID HCL (R)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID HCL 544455-93-8 C16H17NO2
Benzoic acid, 3-amino-2-nitro-, ethyl ester (9CI) Benzoic acid, 3-amino-2-nitro-, ethyl ester (9CI) 193014-01-6 C9H10N2O4
1-Phenylmethyl-L-histidine methyl ester monohydrochloride 1-Phenylmethyl-L-histidine methyl ester monohydrochloride 274927-61-6 C14H18ClN3O2
(+/-)-THREO-3-METHYLGLUTAMIC ACID (+/-)-THREO-3-METHYLGLUTAMIC ACID 63088-04-0 C6H11NO4
3-CHLORO-DL-PHENYLALANINE 3-CHLORO-DL-PHENYLALANINE 14091-12-4 C9H10ClNO2
FMOC-D-PHE(2-I)-OH FMOC-D-PHE(2-I)-OH 478183-65-2 C24H20INO4
N-BOC-DL-SERINE N-BOC-DL-SERINE 69942-12-7 C9H17NO5
2-AMINO-3-PYRIDIN-4-YL-PROPIONIC ACID 2-AMINO-3-PYRIDIN-4-YL-PROPIONIC ACID 139178-88-4 C8H10N2O2
N-BOC-L-CYCLOHEXYLGLYCINOL N-BOC-L-CYCLOHEXYLGLYCINOL 107202-39-1 C13H25NO3
FMOC-(S)-3-AMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(2-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 507472-19-7 C25H20F3NO4
L-GLUTAMIC-2,3,3,4,4-D5 ACID L-GLUTAMIC-2,3,3,4,4-D5 ACID 2784-50-1 C5H4D5NO4
(R)-3-AMINO-3-(2-METHYL-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(2-METHYL-PHENYL)-PROPIONIC ACID C10H13NO2
FMOC-D-LYS(TEOC)-OH FMOC-D-LYS(TEOC)-OH 198545-00-5 C27H36N2O6Si
(R)-ALPHA-BENZYL-L-PROLINE-HCL (R)-ALPHA-BENZYL-L-PROLINE-HCL 86116-84-9 C12H15NO2
(S)-3,4-DCPG (S)-3,4-DCPG 201730-11-2 C10H9NO6
FMOC-(S)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID 507472-14-2 C24H20FNO4
H-D-ASP-OME H-D-ASP-OME 65414-78-0 C5H9NO4
BOC-D-3,4-DIMETHOXYPHENYLALANINE BOC-D-3,4-DIMETHOXYPHENYLALANINE 218457-71-7 C16H23NO6
3,5-DIAMINOBENZYL ALCOHOL DIHYDROCHLORIDE 3,5-DIAMINOBENZYL ALCOHOL DIHYDROCHLORIDE 28150-15-4 C7H12Cl2N2O
Z-GLY-NH2 Z-GLY-NH2 949-90-6 C10H12N2O3
AC-MURAMYL-ALA-GLU-NH2 AC-MURAMYL-ALA-GLU-NH2 59331-38-3 C19H32N4O11
N-[2-(DIETHYLAMINO)ETHYL]STEARAMIDE N-[2-(DIETHYLAMINO)ETHYL]STEARAMIDE 16889-14-8 C24H50N2O
(S)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID C10H13NO2
N-(9-FLUORENYLMETHOXYCARBONYL)-L-LEUCIN& N-(9-FLUORENYLMETHOXYCARBONYL)-L-LEUCIN& 200937-57-1 C21H23NO4
N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC ACID N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC ACID 104091-09-0 C20H19NO6
N-Benzylglycine ethyl ester hydrochloride N-Benzylglycine ethyl ester hydrochloride 6344-42-9 C11H16ClNO2
L-METHIONINE METHYLSULFONIUM IODIDE L-METHIONINE METHYLSULFONIUM IODIDE 34236-06-1 C6H16INO2S2
BOC-ASP(OALL)-OH BOC-ASP(OALL)-OH 132286-77-2 C12H19NO6
N-Dodecanoyl-4-hydroxy-L-proline N-Dodecanoyl-4-hydroxy-L-proline 135777-18-3 C17H31NO4
Sodium N-tetradecanoyl-L-valinate Sodium N-tetradecanoyl-L-valinate 58185-39-0 C19H36NNaO3
N-Hexadecanoyl-4-hydroxy-L-proline N-Hexadecanoyl-4-hydroxy-L-proline 41736-92-9 C21H39NO4
H-ASP(OTBU)-OTBU HCL H-ASP(OTBU)-OTBU HCL 1791-13-5 C12H24ClNO4
3-(Methylseleno)alanine 3-(Methylseleno)alanine 2574-71-2 C4H9NO2Se
N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE N-ALFA-FMOC-4-(PHOSPHONODIFLUOROMETHYL)-L-PHENYLALANINE 160751-44-0 C25H22F2NO7P
3-AMINO-L-TYROSINE DIHYDROCHLORIDE MONOHYDRATE 3-AMINO-L-TYROSINE DIHYDROCHLORIDE MONOHYDRATE C9H16Cl2N2O4
(S)-(+)-2-CHLOROPHENYLGLYCINE METHYL ESTER HYDROCHLORIDE (S)-(+)-2-CHLOROPHENYLGLYCINE METHYL ESTER HYDROCHLORIDE 213018-92-9 C9H11Cl2NO2
(S)-2-AMINO-3-(2,3-DIFLUORO-PHENYL)-PROPIONIC ACID (S)-2-AMINO-3-(2,3-DIFLUORO-PHENYL)-PROPIONIC ACID 266360-42-3 C9H9F2NO2
H-BETA-ALA-ILE-OH H-BETA-ALA-ILE-OH 104465-34-1 C9H18N2O3
H-CYS(DPM)-OH H-CYS(DPM)-OH 5191-80-0 C16H17NO2S
BOC-D-ORN(Z)-OH BOC-D-ORN(Z)-OH 16937-92-1 C18H26N2O6
H-VAL-PNA H-VAL-PNA 52084-13-6 C11H15N3O3
S-ADENOSYL-L-METHIONINE P-TOLUENESULFONATE SALT S-ADENOSYL-L-METHIONINE P-TOLUENESULFONATE SALT 86562-85-8 C22H30N6O8S2
BOC-D-GLU-OTBU BOC-D-GLU-OTBU 73872-71-6 C14H25NO6
L-2,4,5-TRIFLUOROPHE L-2,4,5-TRIFLUOROPHE 749847-57-2 C9H8F3NO2
Z-PHG-OSU Z-PHG-OSU 146118-22-1 C20H18N2O6
N-BOC-D-CYCLOHEXYLGLYCINOL N-BOC-D-CYCLOHEXYLGLYCINOL 188348-00-7 C13H25NO3
Z-D-NVA-OH Z-D-NVA-OH 42918-89-8 C13H17NO4
Fmoc-Tyr(SO3H)-OH Fmoc-Tyr(SO3H)-OH 181952-24-9 C24H21NO8S
4-(FMOC-HYDRAZINO)-BENZOIC ACID 4-(FMOC-HYDRAZINO)-BENZOIC ACID 214475-53-3 C22H18N2O4
4-N-BOC-AMINO-4-CARBOXYTETRAHYDROTHIOPYRAN 4-N-BOC-AMINO-4-CARBOXYTETRAHYDROTHIOPYRAN 108329-81-3 C11H19NO4S
GLUTARYL-GLY-ARG-AMC HCL GLUTARYL-GLY-ARG-AMC HCL 103213-40-7 C23H31ClN6O7
N,N'-Dibenzyloxycarbonyl-D-lysine N,N'-Dibenzyloxycarbonyl-D-lysine 69677-02-7 C22H26N2O6
BOC-D-HOMOARG(ET)2-OH BOC-D-HOMOARG(ET)2-OH 110761-76-7 C16H32N4O4
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