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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
D-SERINE BENZYL ESTER BENZENESULFONATE D-SERINE BENZYL ESTER BENZENESULFONATE 141527-77-7 C10H13N1O3
(1-METHYL-PIPERIDIN-4-YLAMINO)-ACETIC ACID (1-METHYL-PIPERIDIN-4-YLAMINO)-ACETIC ACID 856437-58-6 C8H16N2O2
D-Arg-Ol D-Arg-Ol C6H16N4O
L-Argininol L-Argininol C6H16N4O
Boc-2,4-Difluoro-D-Phenylalanine Boc-2,4-Difluoro-D-Phenylalanine 167993-24-0 C14H17F2NO4
D-Phe-OBzl HCl D-Phe-OBzl HCl 87004-78-2 C16H18ClNO2
L-Isoleucine ethyl ester hydrochloride L-Isoleucine ethyl ester hydrochloride 567-56-6 C14H9Cl3F2
Aspartic acid calcium salt Aspartic acid calcium salt C4H5CaNO4
N-Acetyl-DL-cyclohexylglycine N-Acetyl-DL-cyclohexylglycine 107020-80-4 C10H17NO3
DL-β-Hydroxynorvaline DL-β-Hydroxynorvaline 489469-34-3 C5H11NO3
3-(1-Methyl-1H-pyrazol-3-yl)aniline 3-(1-Methyl-1H-pyrazol-3-yl)aniline 175202-37-6 C10H11N3
GLYCINE-13C2 GLYCINE-13C2 67836-01-5 C2H5NO2
L-ARGININE ALPHA-KETOISOCAPROATE L-ARGININE ALPHA-KETOISOCAPROATE C12H24N4O5
P-TOLUENESULFONYL-L-ARGININE METHYL ESTER HCL P-TOLUENESULFONYL-L-ARGININE METHYL ESTER HCL 901-47-3 C14H22N4O4S
L-GLUTAMINE ALPHA KETOGLUTARATE(2:1) L-GLUTAMINE ALPHA KETOGLUTARATE(2:1)
2-Bromo-4-methoxybenzonitrile 2-Bromo-4-methoxybenzonitrile 140860-51-1 C8H6BrNO
H-ARG(PBF)-OME HCL H-ARG(PBF)-OME HCL 257288-19-0 C20H33ClN4O5S
FMOC-SER(PO3H2)-OH FMOC-SER(PO3H2)-OH 158171-15-4 C18H18NO8P
BOC-D-THZ-OH BOC-D-THZ-OH 63091-82-7 C9H15NO4S
(R)-ALPHA-(4-FLUOROBENZYL)-PROLINE-HCL (R)-ALPHA-(4-FLUOROBENZYL)-PROLINE-HCL 637020-68-9 C12H14FNO2
2-Amino-N1-(3-hydroxypropyl)butanediamide 2-amino-N4-(3-hydroxypropyl)butanediamide polymer 2-Amino-N1-(3-hydroxypropyl)butanediamide 2-amino-N4-(3-hydroxypropyl)butanediamide polymer 137629-32-4 C14H30N6O6
Z-PHE-ALA-DIAZOMETHYLKETONE Z-PHE-ALA-DIAZOMETHYLKETONE 71732-53-1 C21H22N4O4
(R)-(2-BOC-AMINO)BUTYRIC ACID DICYCLOHEXYLAMINE SALT (R)-(2-BOC-AMINO)BUTYRIC ACID DICYCLOHEXYLAMINE SALT 27494-47-9 C21H40N2O4
(2,3,5,6-TETRAMETHYL-BENZENESULFONYLAMINO)-ACETIC ACID (2,3,5,6-TETRAMETHYL-BENZENESULFONYLAMINO)-ACETIC ACID 379250-94-9 C12H17NO4S
N,N'-BIS(ACRYLOYL)CYSTAMINE N,N'-BIS(ACRYLOYL)CYSTAMINE 60984-57-8 C10H16N2O2S2
L-HOMOPHENYLALANINE HYDROCHLORIDE SALT L-HOMOPHENYLALANINE HYDROCHLORIDE SALT 21176-60-3 C10H14ClNO2
EC 4.1.1.25 EC 4.1.1.25 9002-09-9
1-Azetidinecarboxylicacid,3-(ethylamino)-,1,1-dimethylethylester(9CI) 1-Azetidinecarboxylicacid,3-(ethylamino)-,1,1-dimethylethylester(9CI) 454703-23-2 C10H20N2O2
2-HYDRAZINOCARBONYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 2-HYDRAZINOCARBONYL-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 359803-43-3 C10H19N3O3
(2S,3S)-(2S,3R)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID (2S,3S)-(2S,3R)-2-AMINO-3-HYDROXY-4-METHYLPENTANOIC ACID C12H26N2O6
H-D-Glutamic aicd diethyl ester hydrochloride H-D-Glutamic aicd diethyl ester hydrochloride
L-CYSTINE DIHYDROCHLORIDE L-CYSTINE DIHYDROCHLORIDE 30925-07-6 C6H13ClN2O4S2
(METHYL-PYRIDIN-2-YLMETHYL-AMINO)-ACETIC ACID (METHYL-PYRIDIN-2-YLMETHYL-AMINO)-ACETIC ACID 669083-52-7 C9H12N2O2
(R)-N-BOC-3-BROMO-BETA-PHENYLALANINE (R)-N-BOC-3-BROMO-BETA-PHENYLALANINE 501015-16-3 C14H18BrNO4
3-CYCLOHEXYL-D-ALANINE METHYL ESTER HYDROCHLORIDE 3-CYCLOHEXYL-D-ALANINE METHYL ESTER HYDROCHLORIDE 144644-00-8 C10H20ClNO2
(1S,2S)-trans-N-Boc-2-aminocyclopentanol (1S,2S)-trans-N-Boc-2-aminocyclopentanol 145106-43-0 C10H19NO3
4-Bromo-D-phenylalanine hydrochloride 4-Bromo-D-phenylalanine hydrochloride 122852-33-9 C9H10BrNO2.ClH
N-Methyl-D-proline Monohydrate N-Methyl-D-proline Monohydrate 1217447-61-4 C6H13NO3
N-Tosyl-L-alanine N-Tosyl-L-alanine 21957-58-4 C10H13NO4S
H-Glu(OMe)-OtBu H-Glu(OMe)-OtBu 34582-33-7 C10H20ClNO4
Fmoc-δ-azido-Nva-OH Fmoc-δ-azido-Nva-OH 1097192-04-5 C20H20N4O4
[(1R)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester [(1R)-3-Hydroxy-1-phenylpropyl]carbamic acid benzyl ester 888298-05-3 C17H19NO3
L-HOMOCYSTEINESULFINIC ACID L-HOMOCYSTEINESULFINIC ACID 2686-70-6 C4H9NO4S
FMOC-D-1,2,3,4-TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACID FMOC-D-1,2,3,4-TETRAHYDROISOQUINOLINE-1-CARBOXYLIC ACID 204317-98-6 C25H21NO4
FMOC-D-CYS(STBU)-OH FMOC-D-CYS(STBU)-OH 501326-55-2 C22H25NO4S2
GLYCINE TERT-BUTYL ESTER DIBENZENESULFIMIDE SALT GLYCINE TERT-BUTYL ESTER DIBENZENESULFIMIDE SALT 77284-30-1 C18H24N2O6S2
2-METHYLAMINOMETHYL-1,3-DIOXOLANE 2-METHYLAMINOMETHYL-1,3-DIOXOLANE 57366-77-5 C5H11NO2
AC-ALA-NH2 AC-ALA-NH2 15962-47-7 C5H10N2O2
D-Histidine hydrochloride monohydrate D-Histidine hydrochloride monohydrate 6341-24-8 C6H12ClN3O3
(R)-(-)-2-TERT-BUTYLAMINO-1-PHENYLETHAN& (R)-(-)-2-TERT-BUTYLAMINO-1-PHENYLETHAN& 14467-51-7 C12H19NO
N2-(BENZYLOXYCARBONYL)-N6-TRIFLUOROACETYL-L-LYSINE 95 N2-(BENZYLOXYCARBONYL)-N6-TRIFLUOROACETYL-L-LYSINE 95 14905-30-7 C16H19F3N2O5
DANSYL-L-ALANINE PIPERIDINIUM SALT DANSYL-L-ALANINE PIPERIDINIUM SALT 35021-10-4 C15H18N2O4S
4-DIMETHYL-L-GLUTAMIC ACID 4-DIMETHYL-L-GLUTAMIC ACID 151139-88-7 C7H13NO4
(S)-(-)-2-AMINO-3,3-DIMETHYL-1,1-DIPHENYL-1-BUTANOL (S)-(-)-2-AMINO-3,3-DIMETHYL-1,1-DIPHENYL-1-BUTANOL 144054-70-6 C18H23NO
SELENIUM AMINO ACID SELENIUM AMINO ACID
2-[(2,4-dimethylphenyl)amino]acetic acid 2-[(2,4-dimethylphenyl)amino]acetic acid 66947-32-8 C10H13NO2
b-Alanine, N-[4-[(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxy-2-naphthalenyl)-1H-pyrazol-1-yl]ethyl]benzoyl]- b-Alanine, N-[4-[(1S)-1-[3-(3,5-dichlorophenyl)-5-(6-methoxy-2-naphthalenyl)-1H-pyrazol-1-yl]ethyl]benzoyl]- 870823-12-4 C32H27Cl2N3O4
3-(2-FURYL)-L-ALANINE 3-(2-FURYL)-L-ALANINE 121786-31-0 C7H9NO3
N-(methylsulfonyl)glycine N-(methylsulfonyl)glycine 35688-18-7 C3H7NO4S
HEPTAMINOL HYDROCHLORIDE HEPTAMINOL HYDROCHLORIDE 543-15-7 C8H20ClNO
AC-THR-ILE-NLE-((R))-NLE-GLN-ARG-NH2 AC-THR-ILE-NLE-((R))-NLE-GLN-ARG-NH2 128657-47-6 C35H67N11O8
BOC-TRP-N(OCH3)CH3 BOC-TRP-N(OCH3)CH3 97530-05-7 C18H25N3O4
DL-N-BENZOYL-2-ISOBUTYLSERINE DL-N-BENZOYL-2-ISOBUTYLSERINE 52421-47-3 C14H19NO4
FMOC-4-AMINOBENZOIC ACID FMOC-4-AMINOBENZOIC ACID 185116-43-2 C22H17NO4
N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE N-(3-OXOOCTANOYL)-DL-HOMOSERINE LACTONE 106983-27-1 C12H19NO4
(2R 3S)-(-)-4-DIMETHYLAMINO-1 2-DIPHENY& (2R 3S)-(-)-4-DIMETHYLAMINO-1 2-DIPHENY& 72541-03-8 C19H25NO
N-BENZYLPHENYLGLYCINE METHYL ESTER N-BENZYLPHENYLGLYCINE METHYL ESTER 137307-61-0 C16H17NO2
POLY-PREP SLIDES POLY-PREP SLIDES
L-ALANINE METHYL ESTER L-ALANINE METHYL ESTER 114041-77-9 C4H9NO
FMOC-NIP-OH FMOC-NIP-OH 158922-07-7 C21H21NO4
(S)-PIPERAZINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER (S)-PIPERAZINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER C10H18N2O4
L-2,4-DIMETHYLPHE L-2,4-DIMETHYLPHE 259726-56-2 C11H15NO2
FMOC-D-CYS(MBZL)-OH FMOC-D-CYS(MBZL)-OH 200354-41-2 C26H25NO4S
L-PROLINE-15N L-PROLINE-15N 59681-31-1 C5H9NO2
2-AMINOQUINOLINE-3-CARBOXYLIC ACID 2-AMINOQUINOLINE-3-CARBOXYLIC ACID 31407-29-1 C10H8N2O2
Glycyl-DL-alanine Glycyl-DL-alanine 2325-50-0 C5H10N2O3
N2-(1-oxohexadecyl)-L-arginine N2-(1-oxohexadecyl)-L-arginine 58725-47-6 C22H44N4O3
L-lysine L-ascorbate L-lysine L-ascorbate 24404-95-3 C12H22N2O8
(R)-phenylglycine hydrochloride (R)-phenylglycine hydrochloride 25705-52-6 C8H10ClNO2
bis(2-octyldodecyl) N-(1-oxododecyl)-L-glutamate bis(2-octyldodecyl) N-(1-oxododecyl)-L-glutamate 82204-94-2 C57H111NO5
L-Phenylalanine benzyl ester hydrocholride L-Phenylalanine benzyl ester hydrocholride C16H18ClNO2
3-Hydroxyglutamic acid hydrochloride 3-Hydroxyglutamic acid hydrochloride C5H10ClNO5
N-FMOC-L-aspartic acid 4-t-butyl ester N-FMOC-L-aspartic acid 4-t-butyl ester C23H25NO6
Glycyl-L-histidine Glycyl-L-histidine C8H12N4O3
NR2B (Glutamate receptor) NR2B (Glutamate receptor)
HisX6 HisX6
Anti-GAD-65 (glutamate decarboxylase) Anti-GAD-65 (glutamate decarboxylase)
Anti-SYK (Spleen tyrosine kinase) Anti-SYK (Spleen tyrosine kinase)
2-Hydroxy-5-Nitro-Phenylalanine 2-Hydroxy-5-Nitro-Phenylalanine C9H10N2O5
N-Acetyl-D-Glutamine N-Acetyl-D-Glutamine C7H12N2O4
D-Lysine methyl ester hydrochloride D-Lysine methyl ester hydrochloride C7H17ClN2O2
D-Threonine ethyl ester hydrochloride D-Threonine ethyl ester hydrochloride 62365-20-2 C6H14ClNO3
β-thiolleucine β-thiolleucine C6H13NO2S
DIHYDROXYETHYL STEARYL GLYCINATE DIHYDROXYETHYL STEARYL GLYCINATE 24120-14-7 C22H45NO4
DIOCTYLDODECETH-2 LAUROYL GLUTAMATE DIOCTYLDODECETH-2 LAUROYL GLUTAMATE
LYSINE ASPARTATE LYSINE ASPARTATE C10H21N3O6
PALMITOYL GLYCINE PALMITOYL GLYCINE 2441-41-0 C18H35NO3
potassium cocoyl glycinate potassium cocoyl glycinate 301341-58-2 C28H53KNO5+
DIETHYL GLUTAMATE DIETHYL GLUTAMATE 16450-41-2 C9H17NO4
DL-homoleucine DL-homoleucine
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