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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
GRA Ex-25 GRA Ex-25 307983-31-9 C29H36F3N3O5
N-Phenyl-N-nitrosoglycine N-Phenyl-N-nitrosoglycine 6415-68-5 C8H8N2O3
(S)-(+)-NALPHA-BENZYL-NBETA-BOC-O-BENZYL-L-HYDRAZINOTYROSINE DICYCLOHEXYLAMINE SALT (S)-(+)-NALPHA-BENZYL-NBETA-BOC-O-BENZYL-L-HYDRAZINOTYROSINE DICYCLOHEXYLAMINE SALT 680601-76-7 C40H55N3O5
3-(2-Pyridyl)alanine 3-(2-Pyridyl)alanine 163513-22-2 C9H13ClN2O2
3 3' 5-TRIIODO-L-THYRONINE  SODIUM SALT& 3 3' 5-TRIIODO-L-THYRONINE SODIUM SALT& 345957-19-9 C15H11I3NO4Na
7,8-DIAMINOPELARGONIC ACID 7,8-DIAMINOPELARGONIC ACID 21738-21-6 C9H20N2O2
(R)-2-(+)-AMINO-1,1,2-TRIPHENYLETHANOL (R)-2-(+)-AMINO-1,1,2-TRIPHENYLETHANOL 79868-79-4 C20H19NO
L-LEUCINE-2-D1 L-LEUCINE-2-D1 89836-93-1 C6H13NO2
GAMMA-GLUTAMYL-S-ALLYL-L-CYSTEINE (25 MG) GAMMA-GLUTAMYL-S-ALLYL-L-CYSTEINE (25 MG)
L-METHIONINE GAMMA-LYASE L-METHIONINE GAMMA-LYASE 42616-25-1 C9H14N2O12P2
MANGANESE ASPARTATE MANGANESE ASPARTATE C4H5MnNO4
4-methyloxazolidine-2,5-dione 4-methyloxazolidine-2,5-dione 30291-41-9 C4H5NO3
O-benzyl-L-methionine toluene-p-sulphonate O-benzyl-L-methionine toluene-p-sulphonate 68739-90-2 C19H25NO5S2
N-CBZ-O-t-butyl-L-tyrosine dicyclohexylammonium salt N-CBZ-O-t-butyl-L-tyrosine dicyclohexylammonium salt C33H48N2O5
N-FMOC-S-tert-butyl-L-cysteine N-FMOC-S-tert-butyl-L-cysteine C22H25NO4S
DL-Glutamine 15N DL-Glutamine 15N C5H10N2O3
L-Glutamic acid-γ-(4-methoxy-2-naphthylamide) L-Glutamic acid-γ-(4-methoxy-2-naphthylamide) C16H18N2O4
N-CBZ-L-glutamic acid-5-benzyl ester N-CBZ-L-glutamic acid-5-benzyl ester C20H21NO6
N-(4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-L-Glutamic Acid Diethyl Ester P-Tluensulfonic Acid salt N-(4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-L-Glutamic Acid Diethyl Ester P-Tluensulfonic Acid salt
N-Boc-N-methyl-Phe N-Boc-N-methyl-Phe
L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) L-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) 81102-38-7 C6H11NO3
L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI) L-Proline, 4-hydroxy-1-methyl-, methyl ester, trans- (9CI) 13135-69-8 C7H13NO3
BOC-L-ALANINE-NCA BOC-L-ALANINE-NCA 125814-30-4 C9H13NO5
L-Cysteine hydrochloride Monohydrate L-Cysteine hydrochloride Monohydrate C3H10ClNO3S
L- Arginine Orotate L- Arginine Orotate C11H18N6O6
3-amino-4-trifluoromethylbenzoic acid
3-amino-4-trifluoromethylbenzoic acid C8H6F3NO2
3-Amino-5-bromobenzoic acid 98% 3-Amino-5-bromobenzoic acid 98% C7H6BrNO2
L-ARGININE L-MALATE(1:1) L-ARGININE L-MALATE(1:1)
DJENKOLIC ACID, L-(P) DJENKOLIC ACID, L-(P)
2,3-Pyridinedicarboxylicacid,4-amino-,dimethylester(9CI) 2,3-Pyridinedicarboxylicacid,4-amino-,dimethylester(9CI) 122475-56-3 C9H10N2O4
CMDA CMDA 122665-73-0 C17H23ClN2O8S
4'-N,N-dimethylamino-1'-phenylazo-3-pyridine 4'-N,N-dimethylamino-1'-phenylazo-3-pyridine 156-25-2 C13H14N4
4-nitrophenyl glycinate 4-nitrophenyl glycinate 17639-39-3 C8H8N2O4
L-β-Homo-Tyr-OH.HCl L-β-Homo-Tyr-OH.HCl 615537-19-4 C10H13NO3
N-[(3beta)-3-Hydroxy-28-oxoolean-12-en-28-yl]-glycine N-[(3beta)-3-Hydroxy-28-oxoolean-12-en-28-yl]-glycine 851475-58-6 C32H51NO4
METHYL N-BENZOYL-4-HYDROXYPROLINATE METHYL N-BENZOYL-4-HYDROXYPROLINATE 31560-20-0 C13H15NO4
L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6 L-TYROSINE, N-[(1,1-DIMETHYL ETHOXY) CARBONYL]-2,6 137650-15-8 C17H25NO5
(S)-Acetylamino-(4-fluoro-phenyl)-acetic acid (S)-Acetylamino-(4-fluoro-phenyl)-acetic acid C10H10FNO3
COPPER AMINO ACID COPPER AMINO ACID
MAGNESIUM AMINO ACID MAGNESIUM AMINO ACID
LEUCINE, N-[(3-CHLOROPHENYL)SULFONYL]- LEUCINE, N-[(3-CHLOROPHENYL)SULFONYL]- C12H16ClNO4S
GAD-65 (glutamate decarboxylase) GAD-65 (glutamate decarboxylase)
Eukaryotic aspartyl protease(Rice) Eukaryotic aspartyl protease(Rice)
Trk C(Tyrosine kinase,TrkC) Trk C(Tyrosine kinase,TrkC)
(S)-beta-4-Bromophenylalanine (S)-beta-4-Bromophenylalanine C9H10BrNO2
DL-Ala-OBzlTosOH DL-Ala-OBzlTosOH C10H13NO2C7H8NO3
α-amino-β-cyclohexylpropionic acid α-amino-β-cyclohexylpropionic acid C9H17NO2
Pyrazinyl-L-alanine Pyrazinyl-L-alanine 87831-85-4 C7H9N3O2
L-Tyrosine alpha Ketoglutarate (2:1) L-Tyrosine alpha Ketoglutarate (2:1)
DIETHYL PALMITOYL ASPARTATE DIETHYL PALMITOYL ASPARTATE 3397-14-6 C24H45NO5
DIMETHYL ASPARTIC ACID DIMETHYL ASPARTIC ACID 1115-22-6 C6H11NO4
GLYCYL TYROSINE GLYCYL TYROSINE 39630-46-1 C11H16N2O5
PHENYLALANINE PHENYLALANINE 167088-01-9 C9H11NO2
(2R,4S)-4-Fluoro-D-proline methyl ester (2R,4S)-4-Fluoro-D-proline methyl ester 732957-04-9 C6H10FNO2
β-hydroxynorleucine β-hydroxynorleucine C6H13NO3
EC 3.3.1.1 EC 3.3.1.1 9025-54-1
TYR-D-ALA-GLY-PHE-MET ACOH H2O TYR-D-ALA-GLY-PHE-MET ACOH H2O 100929-62-2 C30H43N5O10S
POLY-L-ASPARTIC ACID SODIUM SALT POLY-L-ASPARTIC ACID SODIUM SALT 34345-47-6 C4H6NNaO4
H-ABU-OME HCL H-ABU-OME HCL 56545-22-3 C5H12ClNO2
erythro-N-[(Phenylmethoxy)carbonyl]-3-allyl-L-aspartic acid 1-tert-butyl ester erythro-N-[(Phenylmethoxy)carbonyl]-3-allyl-L-aspartic acid 1-tert-butyl ester 123975-62-2 C19H25NO6
Glycine 1-methylethyl ester Glycine 1-methylethyl ester 13048-66-3 C5H11NO2
5-Methyl-DL-Norleucine 5-Methyl-DL-Norleucine C7H15NO2
Boc-D-2-CL-Phe-Oet Boc-D-2-CL-Phe-Oet
Boc-L-beta-homo-Val Boc-L-beta-homo-Val
D-(2-Thi)-Gly D-(2-Thi)-Gly
Fmoc-D-3-AMP(Boc) Fmoc-D-3-AMP(Boc)
Fmoc-L-beta-homo-Val Fmoc-L-beta-homo-Val
L-(2-Thi)-Gly L-(2-Thi)-Gly
4-Methyl-3-(trifluoromethyl)-DL-phenylalanine, JRD, 97% 4-Methyl-3-(trifluoromethyl)-DL-phenylalanine, JRD, 97%
Fmoc-L-threonine monohydrate Fmoc-L-threonine monohydrate 229957-49-7 C19H21NO6
3-(3-Pyridyl)-DL-alanine 3-(3-Pyridyl)-DL-alanine 105381-95-1 C8H10N2O2
Cbz-4-Trifluoromethyl-L-Phenylalanine Cbz-4-Trifluoromethyl-L-Phenylalanine C18H16F3NO4
D-Alanine 4-nitroanilide hydrochloride D-Alanine 4-nitroanilide hydrochloride 81086-57-9 C9H11ClN2O4
L-4-Aminophenylglycine L-4-Aminophenylglycine C8H10N2O2
N2-(1-Oxododecyl)-DL-arginine N2-(1-Oxododecyl)-DL-arginine 133849-37-3 C18H36N4O3
2-Chlorophenylalanine hydrochloride 2-Chlorophenylalanine hydrochloride 120108-63-6 C9H11Cl2NO2
Chromium Glycine Chromium Glycine C6H12CrN3O6
β,β-dimethylaspartic β,β-dimethylaspartic
β-methyl-β-hydroxyas β-methyl-β-hydroxyas
Fmoc-(4-T-BUTOXYCARBONYLAMINO)-D-PHENYLALANINE Fmoc-(4-T-BUTOXYCARBONYLAMINO)-D-PHENYLALANINE C29H30N2O6
Boc-3-Bromo-DL-Phenylalanine Boc-3-Bromo-DL-Phenylalanine C14H18BrNO4
N~2~-methylalaninamide(SALTDATA: FREE) N~2~-methylalaninamide(SALTDATA: FREE) 32012-16-1 C4H10N2O
N~1~,N~1~,N~3~-trimethyl-beta-alaninamide(SALTDATA: FREE) N~1~,N~1~,N~3~-trimethyl-beta-alaninamide(SALTDATA: FREE) 17268-50-7 C6H14N2O
(S)-(+)-2-(2-Chlorophenyl)glycine Methyl Ester Tartrate (S)-(+)-2-(2-Chlorophenyl)glycine Methyl Ester Tartrate C13H16ClNO8
N-Acetyl-L-Hydroxyproline N-Acetyl-L-Hydroxyproline C7H11NO4
2-(Trifluoromethyl)-D-proline 2-(Trifluoromethyl)-D-proline 921224-82-0 C6H8F3NO2
trans-4-(1-NaphthylMethyl)-L-proline hydrochloride, 95% trans-4-(1-NaphthylMethyl)-L-proline hydrochloride, 95% C16H18ClNO2
2-Methyl-5-(trifluoroMethyl)-DL-phenylalanine, JRD, 97% 2-Methyl-5-(trifluoroMethyl)-DL-phenylalanine, JRD, 97%
trans-4-(4-BroMobenzyl)-L-proline hydrochloride, 95% trans-4-(4-BroMobenzyl)-L-proline hydrochloride, 95% C12H15BrClNO2
trans-4-(4-Chlorobenzyl)-L-proline hydrochloride, 95% trans-4-(4-Chlorobenzyl)-L-proline hydrochloride, 95% C12H15Cl2NO2
4-Allyloxy-N-Boc-L-phenylalanine, 95% 4-Allyloxy-N-Boc-L-phenylalanine, 95% 1175919-93-3 C17H23NO5
trans-4-Benzyl-N-Boc-L-proline, 95% trans-4-Benzyl-N-Boc-L-proline, 95% C17H23NO4
N-Boc-4-Methylene-L-proline Methyl Ester N-Boc-4-Methylene-L-proline Methyl Ester 84348-39-0 C12H19NO4
L-HoMophenylalanine tert-Butyl Ester Hydrochloride L-HoMophenylalanine tert-Butyl Ester Hydrochloride 130316-46-0 C14H22ClNO2
N-salicylideneaMino acid LanthanuM(Ⅲ) N-salicylideneaMino acid LanthanuM(Ⅲ)
Sofosbuvir Sofosbuvir 1190307-88-0 C22H29FN3O9P
D-Asparitc acid 4-Methyl ester HCl D-Asparitc acid 4-Methyl ester HCl C5H10ClNO4
IMp. B (EP): L-Cysteine IMp. B (EP): L-Cysteine
(2S,4R)-Methyl 1-benzoyl-4-(tosylo×y)pyrrolidine-2-carbo×ylate (2S,4R)-Methyl 1-benzoyl-4-(tosylo×y)pyrrolidine-2-carbo×ylate 31560-21-1 C20H21NO6S
H-Glu-Obzl.HCl H-Glu-Obzl.HCl
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