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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
DL-THREO-3-PHENYLSERINE HYDRATE, 99 DL-THREO-3-PHENYLSERINE HYDRATE, 99 332383-91-2 C9H13NO4
GLYCINE, SODIUM SALT HYDRATE, 99 GLYCINE, SODIUM SALT HYDRATE, 99 207300-76-3 C2H4NNaO2.xH2O
GLYCINE  SODIUM SALT HYDRATE  98 GLYCINE SODIUM SALT HYDRATE 98 313222-98-9 H2NCH2CO2NaxH2O
L-PHENYL-D5-ALANINE L-PHENYL-D5-ALANINE 56253-90-8 C9H6D5NO2
3-(DIBENZYLAMINO)-1-PROPANOL 3-(DIBENZYLAMINO)-1-PROPANOL 3161-51-1 C17H21NO
CREATINE PHOSPHATE DISODIUM SALT TETRAHYDRATE CREATINE PHOSPHATE DISODIUM SALT TETRAHYDRATE 71519-72-7 C4H13N3NaO6P
PAM3-CYS-ALA-GLY-OH PAM3-CYS-ALA-GLY-OH 117858-54-5 C59H111N3O9S
D-M-TYROSINE D-M-TYROSINE C9H11NO3
4-TRIFLUOROMETHYL-L-PHENYLALANINE HYDROCHLORIDE 4-TRIFLUOROMETHYL-L-PHENYLALANINE HYDROCHLORIDE 122839-50-3 C10H11ClF3NO2
(R)-(-)-N-BENZYL-2-PHENYLGLYCINOL (R)-(-)-N-BENZYL-2-PHENYLGLYCINOL 14231-57-3 C15H17NO
FMOC-2-(2-AMINOETHOXY)ETHANOL FMOC-2-(2-AMINOETHOXY)ETHANOL 299430-87-8 C19H21NO4
Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate Methyl 2-((tert-butoxycarbonyl)amino)-3-iodopropanoate 889670-02-4 C9H16INO4
4-Nitro-D-phenylalanine hydrochloride 4-Nitro-D-phenylalanine hydrochloride 147065-06-3 C9H11ClN2O4
O-(2-Nitrobenzyl)-L-tyrosine Hydrochloride O-(2-Nitrobenzyl)-L-tyrosine Hydrochloride 207727-86-4 C16H17ClN2O5
L-Norvaline, 5-hydroxy-N- [(phenylmethoxy)carbonyl]-, 1,1-dimethylethylester L-Norvaline, 5-hydroxy-N- [(phenylmethoxy)carbonyl]-, 1,1-dimethylethylester 124620-51-5 C17H25NO5
(R)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-2-METHYL-HEPT-6-ENOIC ACID (R)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-2-METHYL-HEPT-6-ENOIC ACID 288617-77-6 C23H25NO4
DL-Lysine monohydrate DL-Lysine monohydrate 885701-25-7 C6H16N2O3
(S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate (S)-1-Benzyl 2-Methyl 4-Oxopyrrolidine-1,2-Dicarboxylate 16217-15-5 C14H15NO5
S-METHYL-L-CYSTEINE METHYL ESTER HYDROCHLORIDE S-METHYL-L-CYSTEINE METHYL ESTER HYDROCHLORIDE 34017-27-1 C5H12ClNO2S
L-Norvaline, 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-, 1,1-dimethylethylester L-Norvaline, 5-[(methylsulfonyl)oxy]-N-[(phenylmethoxy)carbonyl]-, 1,1-dimethylethylester 159877-09-5 C18H27NO7S
BOC-ORN(ALOC)-OH BOC-ORN(ALOC)-OH 171820-74-9 C14H24N2O6
FMOC-D-ASP(2-PHENYLISOPROPYL ESTER)-OH FMOC-D-ASP(2-PHENYLISOPROPYL ESTER)-OH 214852-39-8 C28H27NO6
BOC-ASP(OTBU)-OSU BOC-ASP(OTBU)-OSU 50715-50-9 C17H26N2O8
N-CARBOBENZYLOXY-D-SERINE METHYL ESTER N-CARBOBENZYLOXY-D-SERINE METHYL ESTER 93204-36-5 C12H15NO5
STA STA
1-PALMITOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT 1-PALMITOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT 143077-66-1 C22H43NNaO9P
POLY(GAMMA-METHYL L-GLUTAMATE) POLY(GAMMA-METHYL L-GLUTAMATE) 25086-16-2 (C6H11NO4)x
L-NORVALINE T-BUTYL ESTER L-NORVALINE T-BUTYL ESTER 15911-75-8 C9H19NO2
(S)-1-BENZYL-5-CARBOXY-2-PYRROLIDINONE (S)-1-BENZYL-5-CARBOXY-2-PYRROLIDINONE 7535-59-3 C12H13NO3
N-Acetyl-L-prolinamide N-Acetyl-L-prolinamide 16395-58-7 C7H12N2O2
3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE 3-CHLORO-D-ALANINE METHYL ESTER,HYDROCHLORIDE 112346-82-4 C4H9Cl2NO2
(S)-N-BOC-4-FLUOROPHENYLGLYCINE (S)-N-BOC-4-FLUOROPHENYLGLYCINE 142186-36-5 C13H16FNO4
N-[[5-(dimethylamino)-1-naphthyl]sulphonyl]-L-alanine, compound with piperidine (1:1) N-[[5-(dimethylamino)-1-naphthyl]sulphonyl]-L-alanine, compound with piperidine (1:1) 83803-56-9 C20H29N3O4S
D (-) Dihydro Phenylglycine Sodium Dane Salt D (-) Dihydro Phenylglycine Sodium Dane Salt
3-Cumaronylalanine 3-Cumaronylalanine C11H11NO3
Aspartic acid magmesium salt Aspartic acid magmesium salt C4H5MgNO4
S-Allyl-L-cysteine hydrochloride S-Allyl-L-cysteine hydrochloride 60114-85-4 C6H12ClNO2S
D-Homoarginine hydrochloride D-Homoarginine hydrochloride C7H17ClN4O2
L-Cyclopentylalanine L-Cyclopentylalanine C8H15NO2
N-(4-Aminobenzoyl)-DL-glutamic acid N-(4-Aminobenzoyl)-DL-glutamic acid 4230-33-5 C12H14N2O5
FMOC-(S)-3-THIENYLGLYCINE FMOC-(S)-3-THIENYLGLYCINE C21H17NO4S
2-METHYL-3-(2-METHYL-PIPERIDIN-1-YL)-PROPAN-1-OL 2-METHYL-3-(2-METHYL-PIPERIDIN-1-YL)-PROPAN-1-OL C10H21NO
copper lysinate copper lysinate C12H26CuN4O4
Nitrocaphane Nitrocaphane 54940-95-3 C14H19O4N3CL2
1,2,5-Oxadiazole-3-carboxylicacid,4-amino-,methylester(9CI) 1,2,5-Oxadiazole-3-carboxylicacid,4-amino-,methylester(9CI) 159013-94-2 C4H5N3O3
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(3-chloro-4-hydroxyphenyl)propanoic acid 478183-58-3 C24H20ClNO5
5-(Dimethylamino)nicotinic Acid 5-(Dimethylamino)nicotinic Acid 30766-20-2 C8H10N2O2
ARGININOSUCCINIC ACID DISODIUM SALT ARGININOSUCCINIC ACID DISODIUM SALT 156637-58-0 C11H18N4Na2O6
Potassium hydrogen DL-aspartate Potassium hydrogen DL-aspartate 923-09-1 C4H6KNO4
LEUCINE, N-[[3-(TRIFLUOROMETHYL)PHENYL]SULFONYL]- LEUCINE, N-[[3-(TRIFLUOROMETHYL)PHENYL]SULFONYL]- 251097-65-1 C13H16F3NO4S
N-ALPHA-ACETYL-L-LYSINE-N-METHYLAMIDE MONOHYDRATE N-ALPHA-ACETYL-L-LYSINE-N-METHYLAMIDE MONOHYDRATE 81013-00-5 C9H21N3O3
4-AZA-DL-LEUCINE DIHYDROCHLORIDE 4-AZA-DL-LEUCINE DIHYDROCHLORIDE 102029-69-6 C5H14Cl2N2O2
O-Methyl-D-tyrosine hydrochloride O-Methyl-D-tyrosine hydrochloride 70601-63-7 C10H13NO3.ClH
Dipeptide diaminobutyroyl benzylamide diacetate Dipeptide diaminobutyroyl benzylamide diacetate 823202-99-9 C19H29N5O3.2(C2H4O2)
L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 1-1-methylethyl) ester L-Glutamic acid, N-[(phenylmethoxy)carbonyl]-, 1-1-methylethyl) ester 88815-54-7 C16H21NO6
L-THREONINE-15N L-THREONINE-15N 252743-41-2 C4H9NO3
O-Benzyl-DL-Serine O-Benzyl-DL-Serine 32520-12-0 C10H13NO3
(N-(3-TRIFLUOROMETHYL)BENZENESULFONYL)ALANINE (N-(3-TRIFLUOROMETHYL)BENZENESULFONYL)ALANINE 288266-54-6 C10H10F3NO4S
(1-METHYL-PIPERIDIN-4-YLAMINO)-ACETIC ACID (1-METHYL-PIPERIDIN-4-YLAMINO)-ACETIC ACID 856437-58-6 C8H16N2O2
2-METHYL-5-HYDROXYTRYPTAMINE 2-METHYL-5-HYDROXYTRYPTAMINE 78263-90-8 C11H14N2O
N-DECANOYL-DL-HOMOSERINE LACTONE* N-DECANOYL-DL-HOMOSERINE LACTONE* 106983-36-2 C14H25NO3
(S)-(+)-NALPHA-BENZYL-NBETA-BOC-L-HYDRAZINOTRYPTOPHANE (S)-(+)-NALPHA-BENZYL-NBETA-BOC-L-HYDRAZINOTRYPTOPHANE 188777-50-6 C23H27N3O4
D-SERINE BENZYL ESTER BENZENESULFONATE D-SERINE BENZYL ESTER BENZENESULFONATE 141527-77-7 C10H13N1O3
N-(BENZLOXYCARBONYL)-3-AMINO-1 2- N-(BENZLOXYCARBONYL)-3-AMINO-1 2- 108587-40-2 C11H15NO4
POLY-L -SERINE POLY-L -SERINE 25821-52-7 C3H7NO3
Z-LYS(ALOC)-OH DCHA Z-LYS(ALOC)-OH DCHA 220369-84-6 C18H24N2O6
FMOC-SER-OME FMOC-SER-OME 82911-78-2 C19H19NO5
Fmoc-6-chloro L-Tryptophan Fmoc-6-chloro L-Tryptophan 908847-42-7 C26H21ClN2O4
N-Benzoyl-beta-alanine Methyl Ester N-Benzoyl-beta-alanine Methyl Ester 89928-06-3 C11H13NO3
L-METHIONINE (15N) L-METHIONINE (15N) 82572-25-6 C5H11NO2S
L-ASPARTIC ACID POTASSIUM MAGNESIUM SALT L-ASPARTIC ACID POTASSIUM MAGNESIUM SALT 67528-13-6 C16H24K2MgN4O16
PPACK, DIHYDROCHLORIDE PPACK, DIHYDROCHLORIDE 142036-63-3 C21H32Cl2N6O3
FMOC-D-DAP(DDE)-OH FMOC-D-DAP(DDE)-OH 210830-03-8 C28H30N2O6
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
FMOC-SER(PO3H2)-OH FMOC-SER(PO3H2)-OH 158171-15-4 C18H18NO8P
H-ARG(PBF)-OME HCL H-ARG(PBF)-OME HCL 257288-19-0 C20H33ClN4O5S
2-Bromo-4-methoxybenzonitrile 2-Bromo-4-methoxybenzonitrile 140860-51-1 C8H6BrNO
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
P-TOLUENESULFONYL-L-ARGININE METHYL ESTER HCL P-TOLUENESULFONYL-L-ARGININE METHYL ESTER HCL 901-47-3 C14H22N4O4S
L-ARGININE ALPHA-KETOISOCAPROATE L-ARGININE ALPHA-KETOISOCAPROATE C12H24N4O5
L-GLUTAMINE ALPHA KETOGLUTARATE(2:1) L-GLUTAMINE ALPHA KETOGLUTARATE(2:1)
GLYCINE-13C2 GLYCINE-13C2 67836-01-5 C2H5NO2
D-Arg-Ol D-Arg-Ol C6H16N4O
L-Argininol L-Argininol C6H16N4O
D-Phe-OBzl HCl D-Phe-OBzl HCl 87004-78-2 C16H18ClNO2
Boc-2,4-Difluoro-D-Phenylalanine Boc-2,4-Difluoro-D-Phenylalanine 167993-24-0 C14H17F2NO4
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
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