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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
L-gamma-Glutamyl-S-[[(4-bromophenyl)hydroxyamino]carbonyl]-L-cysteinylglycine diethyl ester monohydrochloride L-gamma-Glutamyl-S-[[(4-bromophenyl)hydroxyamino]carbonyl]-L-cysteinylglycine diethyl ester monohydrochloride 221174-33-0 C21H30BrClN4O8S
1-CBZ-3-AMINOMETHYLAZETIDINE 1-CBZ-3-AMINOMETHYLAZETIDINE 1016731-24-0 C12H16N2O2
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-dimethyl ester 4-methylbenzenesulfonate N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-dimethyl ester 4-methylbenzenesulfonate 1215090-73-5 C22H25N5O6.C7H8O3S
Fmoc-L-Cysteine Fmoc-L-Cysteine 135248-89-4 C18H17NO4S
1-[1-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-prolyl]-D-proline 1-[1-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-prolyl]-D-proline 144575-00-8 C25H26N2O5
H-Tle-OH·HCl H-Tle-OH·HCl
erythro-N-Boc-3,5-difluoro-L-phenylalanine epoxide, 95% erythro-N-Boc-3,5-difluoro-L-phenylalanine epoxide, 95%
trans-N-Boc-4-(2-naphthylMethyl)-L-proline, 95% trans-N-Boc-4-(2-naphthylMethyl)-L-proline, 95% C21H25NO4
2-AMino-3-(4-aMino-3-hydroxy-phenyl)-propionic acid 2-AMino-3-(4-aMino-3-hydroxy-phenyl)-propionic acid 88686-28-6 C9H12N2O3
N-Butadecanoyl-D-alanine N-Butadecanoyl-D-alanine 114414-86-7 C17H33NO3
N-Butadecanoyl-D-phenylglycine sodiuM salt N-Butadecanoyl-D-phenylglycine sodiuM salt
N-Octadecanoyl-D-alanine N-Octadecanoyl-D-alanine 886202-59-1 C21H41NO3
N-Octadecanoyl-D-phenylglycine sodiuM salt N-Octadecanoyl-D-phenylglycine sodiuM salt C26H42NNaO3
N-Boc protected D-4-hydroxyphenylglycine N-Boc protected D-4-hydroxyphenylglycine 27460-85-1 C13H17NO5
N-t-butylglycine tert-butyl ester N-t-butylglycine tert-butyl ester 916885-51-3 C10H21NO2
N-(2-(Bis(carboxymethyl)amino]ethyl)-N-(1-oxononyl)glycine N-(2-(Bis(carboxymethyl)amino]ethyl)-N-(1-oxononyl)glycine 199387-97-8 C17H30N2O7
ZINC CYSTEINATE ZINC CYSTEINATE C6H12N2O4S2Zn
N-(3-N-BUTOXY-2-HYDROXYPROPYL)IMINODIACETIC ACID MONOSODIUM SALT N-(3-N-BUTOXY-2-HYDROXYPROPYL)IMINODIACETIC ACID MONOSODIUM SALT 32046-75-6 C11H20NNaO6
DL-2-AMINOBUTYRIC ACID DL-2-AMINOBUTYRIC ACID 80-60-4 C4H9NO2
H-PHE-CHLOROMETHYLKETONE HCL H-PHE-CHLOROMETHYLKETONE HCL 52735-71-4 C10H12ClNO
Boc-D-leu-OH·H<SUB>2</SUB>O Boc-D-leu-OH·H2O 16937-99-18
thiazolidine-2,4-dicarboxylic, acid compound with L-arginine (1:1) thiazolidine-2,4-dicarboxylic, acid compound with L-arginine (1:1) 30986-62-0 C11H21N5O6S
Glycine, N-[2-[(2-hydroxyethyl)amino]ethyl]-, N'-coco acyl derivs., monosodium salts Glycine, N-[2-[(2-hydroxyethyl)amino]ethyl]-, N'-coco acyl derivs., monosodium salts 61791-32-0
Glutamate dehydrogenase from bovine liver Glutamate dehydrogenase from bovine liver
DL-β-Phenylserine monohydrate DL-β-Phenylserine monohydrate
N-FMOC-O-tert-butyl-L-tyrosine N-FMOC-O-tert-butyl-L-tyrosine C28H29NO5
N-Ethyl glycine hydrochloride N-Ethyl glycine hydrochloride C4H10ClNO2
N-CBZ-L-glutamyl-L-tyrosine N-CBZ-L-glutamyl-L-tyrosine C22H24N2O8
Anti-Eukaryotic aspartyl protease(Rice) Anti-Eukaryotic aspartyl protease(Rice)
Anti-EphA2 (EphA2 Receptor) (Ephrin A2 Receptor) Anti-EphA2 (EphA2 Receptor) (Ephrin A2 Receptor)
PTP-1B (Protein-tyrosine phosphatase, non-receptor :p-tyr) PTP-1B (Protein-tyrosine phosphatase, non-receptor :p-tyr)
Trk B(Tyrosine kinase,Pyk2) Trk B(Tyrosine kinase,Pyk2)
D-Isoleucine ethyl ester hydrochloride D-Isoleucine ethyl ester hydrochloride C8H18ClNO2
Leu-OtBu.HCl Leu-OtBu.HCl
Lys-OMe Lys-OMe
α-aminocyclopentylacetic acid α-aminocyclopentylacetic acid C7H13NO2
L-Glysine L-Glysine
L-Tyrosine alpha Ketoglutarate (1:1) L-Tyrosine alpha Ketoglutarate (1:1)
DI-TEA-PALMITOYL ASPARTATE DI-TEA-PALMITOYL ASPARTATE
PEG-4 PROLINE LINOLENATE PEG-4 PROLINE LINOLENATE
SODIUM HYDROGENATED TALLOWOYL GLUTAMATE SODIUM HYDROGENATED TALLOWOYL GLUTAMATE
THENOYL METHIONATE THENOYL METHIONATE 60752-63-8 C10H13NO3S2
N6-(trifluroacetyl)_N2-Carboxy-L-Lysine anhydride N6-(trifluroacetyl)_N2-Carboxy-L-Lysine anhydride C9H11F3N2O4
Cyclopentanecarboxylic acid, 2-amino-, methyl ester (9CI) Cyclopentanecarboxylic acid, 2-amino-, methyl ester (9CI) 342419-20-9 C7H13NO2
N,S-Diacetylcysteine methyl ester N,S-Diacetylcysteine methyl ester C8H13NO4S
Iron methionine Iron methionine C15H30FeN3O6S3
N-benzyl glycine N-benzyl glycine C9H11NO2
3-(TrifluoroMethyl)-D-phenylalanine 3-(TrifluoroMethyl)-D-phenylalanine C10H10F3NO2
Boc-D-Alanine methyl ester Boc-D-Alanine methyl ester C9H17NO4
BOC-MET-OL BOC-MET-OL 51372-93-1 C10H21NO3S
2-Hexanamidoacetic acid 2-Hexanamidoacetic acid 24003-67-6 C8H15NO3
gamma-Glutamyl-S-allyl-L-cysteine gamma-Glutamyl-S-allyl-L-cysteine C11H18N2O5S
Tryptophan Synthase Tryptophan Synthase 9014-52-2 NULL
N,N-Dimethyl-DL-Alanine N,N-Dimethyl-DL-Alanine C5H11NO2
N-BSMOC-L-PROLINE N-BSMOC-L-PROLINE C15H15NO6S
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 146943-43-3 C24H29N5O6
N-alpha-Benzyl-L-alanine  methyl  ester N-alpha-Benzyl-L-alanine methyl ester 31022-10-3 C11H15NO2
Boc-D-beta-Homo-Ala Boc-D-beta-Homo-Ala
D-2,6-Dichlorophenylalanine D-2,6-Dichlorophenylalanine C9H9Cl2NO2
Fmoc-L-3-AMP Fmoc-L-3-AMP
L-2,4-Difluorophenylalanine L-2,4-Difluorophenylalanine C9H9F2NO2
(R)-N-Acetyl-5-Chloro-Trp-OMe (R)-N-Acetyl-5-Chloro-Trp-OMe 114872-81-0 C14H15ClN2O3
Cbz-N-Methyl-D-aspartic acid Cbz-N-Methyl-D-aspartic acid C13H15NO6
Boc-D-Pyr-OBzl Boc-D-Pyr-OBzl 400626-71-3 C17H21NO5
N-Butadecanoyl-D-phenylalanine sodiuM salt N-Butadecanoyl-D-phenylalanine sodiuM salt
(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 74761-42-5 C7H13NO4
N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester 1234490-83-5 C30H39N6O9P
N-Methyl-N-pentyl-beta-alanine methyl ester N-Methyl-N-pentyl-beta-alanine methyl ester 744266-99-7 C10H21NO2
N-Methyl-N-(2-pyridyl)glycine Methyl Ester N-Methyl-N-(2-pyridyl)glycine Methyl Ester 1250236-70-4 C9H12N2O2
1-(2,3,5,6-TetraMethylphenylsulfonyl)-L-proline, 96% 1-(2,3,5,6-TetraMethylphenylsulfonyl)-L-proline, 96% 1009282-06-7 C15H21NO4S
α-L-Asparagine-<sup>15</sup>N α-L-Asparagine-15N
3-(3-benzo(b)thienyl)alanine 3-(3-benzo(b)thienyl)alanine 1956-23-6 C11H11NO2S
N-[(3beta)-3-Hydroxy-28-oxoolean-12-en-28-yl]-L-proline N-[(3beta)-3-Hydroxy-28-oxoolean-12-en-28-yl]-L-proline 851475-45-1 C35H55NO4
3-(4-nitro-phenyl)-L-alanine ethylester 3-(4-nitro-phenyl)-L-alanine ethylester C11H14N2O4
FERROUS AMINO ACID FERROUS AMINO ACID
POLY-D-LEUCINE-POLYETHYLENE GLYCOL MONOMETHYL ETHER POLY-D-LEUCINE-POLYETHYLENE GLYCOL MONOMETHYL ETHER
BOC-5-BROMO-D-TRYPTOPHAN BOC-5-BROMO-D-TRYPTOPHAN 114873-17-5 C16H19BrN2O4
N-ISOPROPYL-N-METHYLGLYCINE N-ISOPROPYL-N-METHYLGLYCINE 108957-96-6 C6H13NO2
Boc-D-3,4-Difluoro-phe-OH Boc-D-3,4-Difluoro-phe-OH
Boc-3-(4-Thiazoyl)-L-alanine Boc-3-(4-Thiazoyl)-L-alanine
Boc-L-beta-Homo-Met Boc-L-beta-Homo-Met
D-alpha-Methyl-4-F-Phe D-alpha-Methyl-4-F-Phe
Erythro-Boc-L-PRG-epoxide Erythro-Boc-L-PRG-epoxide
L-meta-Tyr(OAlly)-HCl L-meta-Tyr(OAlly)-HCl
(R)-N-Boc-5-Hydroxy-Trp-OMe (R)-N-Boc-5-Hydroxy-Trp-OMe 1234880-33-1 C17H22N2O5
Methyl (R)-2-(Benzylamino)-3-hydroxypropanoate Methyl (R)-2-(Benzylamino)-3-hydroxypropanoate 131110-76-4 C11H15NO3
α-Amino-β-methylaminopropionic Acid Hydrochloride α-Amino-β-methylaminopropionic Acid Hydrochloride 20790-76-5 C4H11ClN2O2
DL-Serine hydrazide DL-Serine hydrazide 64616-76-8 C3H9N3O2
Z-DL-Gln-OH Z-DL-Gln-OH 932735-43-8 C13H16N2O5
H-Arg(Tos)-OBzl.TosOH H-Arg(Tos)-OBzl.TosOH 103305-88-0 C27H32N4O7S
Acetyl-D-Homoleucine Acetyl-D-Homoleucine
N-Methyl-D-Serine N-Methyl-D-Serine C4H9NO3
Fmoc-D-Lys-OH Fmoc-D-Lys-OH
DL-Chlorophenylglycine methyl ester hydrochloride DL-Chlorophenylglycine methyl ester hydrochloride 141109-13-9 C9H10ClNO2
3-Methoxyphenylalani 3-Methoxyphenylalani
α-amino-1- cyclohexe α-amino-1- cyclohexe
(4-T-BUTOXYCARBONYLAMINO)-D-PHENYLALANINE (4-T-BUTOXYCARBONYLAMINO)-D-PHENYLALANINE C14H20N2O4
Ac-L-phenylglycine Ac-L-phenylglycine
N-α-Methyl-L-alanine hydrochloride N-α-Methyl-L-alanine hydrochloride 65672-32-4 C4H10ClNO2
(S)-DiMethyl pyrrolidine-1,2-dicarboxylate (S)-DiMethyl pyrrolidine-1,2-dicarboxylate 83541-81-5 C8H13NO4
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