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
(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
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
(S)-(-)-(3-CHLORO-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE (S)-(-)-(3-CHLORO-2-HYDROXYPROPYL)TRIMETHYLAMMONIUM CHLORIDE 101396-91-2 C6H15Cl2NO
Ademetionine 1,4-butanedisulfonate Ademetionine 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
BOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID C14H18FNO4
GLYCINE N-BUTYL ESTER HYDROCHLORIDE GLYCINE N-BUTYL ESTER HYDROCHLORIDE 13048-99-2 C6H14ClNO2
H-CYS(BZL)-OET HCL H-CYS(BZL)-OET HCL 52844-67-4 C12H18ClNO2S
N-FORMYLGLYCINE METHYL ESTER N-FORMYLGLYCINE METHYL ESTER 3154-54-9 C4H7NO3
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
(S)-(+)-1-DIMETHYLAMINO-2-PROPANOL (S)-(+)-1-DIMETHYLAMINO-2-PROPANOL 53636-17-2 C5H13NO
L-4-TRIFLUOROMETHYLPHENYLALANINE L-4-TRIFLUOROMETHYLPHENYLALANINE 122839-56-9 C10H10F3NO2
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
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
ALPHA-METHYL-DL-SERINE ALPHA-METHYL-DL-SERINE 3398-40-1 C4H9NO3
FMOC-MENVA-OH FMOC-MENVA-OH 252049-05-1 C21H23NO4
Fmoc-S-Trityl-L-penicillamine Fmoc-S-Trityl-L-penicillamine 201531-88-6 C39H35NO4S
FMOC-HOCHA-OH FMOC-HOCHA-OH 269078-73-1 C25H29NO4
L-GLUTAMINE-15N2 L-GLUTAMINE-15N2 204451-48-9 C5H10N2O3
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
H-ALA-OBZL HCL H-ALA-OBZL HCL 557-83-5 C10H14ClNO2
CYS-GLY CYS-GLY 19246-18-5 C5H10N2O3S
BOC-(R)-ALPHA-BENZYL-PROLINE BOC-(R)-ALPHA-BENZYL-PROLINE 706806-60-2 C17H23NO4
L-ISOLEUCINE-15N L-ISOLEUCINE-15N 59935-30-7 C6H13NO2
BOC-N,2-DIMETHYLALANINE BOC-N,2-DIMETHYLALANINE 146000-39-7 C10H19NO4
POLY-(ALPHA,BETA)-DL-ASPARTIC ACID SODIUM SALT POLY-(ALPHA,BETA)-DL-ASPARTIC ACID SODIUM SALT 94525-01-6 C4H5NNa2O4
BOC-D-3,3-DIPHENYLALANINE BOC-D-3,3-DIPHENYLALANINE 117027-46-0 C20H23NO4
3-CHLORO-L-TYROSINE HYDROCHLORIDE 3-CHLORO-L-TYROSINE HYDROCHLORIDE 35608-63-0 C9H11Cl2NO3
AC-DL-PHG-OH AC-DL-PHG-OH 15962-46-6 C10H11NO3
(S)-N-Acetyl-2-naphthylalanine (S)-N-Acetyl-2-naphthylalanine 37439-99-9 C15H15NO3
BOC-ALA-ALA-OME BOC-ALA-ALA-OME 19794-10-6 C12H22N2O5
H-SER(TBU)-OTBU HCL H-SER(TBU)-OTBU HCL 51537-21-4 C11H24ClNO3
H-D-ALA-ONAP(1) HCL H-D-ALA-ONAP(1) HCL 213179-01-2 C13H14ClNO2
S-(4-NITROPHENYL)CYSTEINYLGLYCINE HYDROCHLORIDE S-(4-NITROPHENYL)CYSTEINYLGLYCINE HYDROCHLORIDE 382631-41-6 C11H14ClN3O5S
4-(2-AMINOETHYL)BENZOIC ACID HYDROCHLORIDE 4-(2-AMINOETHYL)BENZOIC ACID HYDROCHLORIDE 60531-36-4 C9H12ClNO2
N,N-DIMETHYL-L-VALINE N,N-DIMETHYL-L-VALINE 2812-32-0 C7H15NO2
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
H-GLU(OBZL)-NCA H-GLU(OBZL)-NCA 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-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
BOC-D-2-AMINOSUBERIC ACID BOC-D-2-AMINOSUBERIC ACID 75113-71-2 C13H23NO6
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
(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
METHYL (3S)-3-AMINO-3-PHENYLPROPANOATE METHYL (3S)-3-AMINO-3-PHENYLPROPANOATE 37088-66-7 C10H13NO2
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
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
FMOC-L-PHENYLALANYL CHLORIDE FMOC-L-PHENYLALANYL CHLORIDE 103321-57-9 C24H20ClNO3
BOC-VAL-PRO-ARG-AMC HCL BOC-VAL-PRO-ARG-AMC HCL 70375-24-5 C31H46ClN7O7
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