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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
5-BENZYLOXY-DL-TRYPTOPHAN 5-BENZYLOXY-DL-TRYPTOPHAN 6383-70-6 C18H18N2O3
DL-METHIONINE SULFONE DL-METHIONINE SULFONE 820-10-0 C5H11NO4S
FMOC-ALA-WANG RESIN FMOC-ALA-WANG RESIN C18H16NO3R
FMOC-D-HOMOPHENYLALANINE FMOC-D-HOMOPHENYLALANINE 135994-09-1 C8H6ClN6O3P
S-ADENOSYL-L-METHIONINE S-ADENOSYL-L-METHIONINE 17176-17-9 C15H22N6O5S
CHLOROACETYL-L-VALINE CHLOROACETYL-L-VALINE 2279-16-5 C7H12ClNO3
(1R,4S)-4-Aminocyclopent-2-enecarboxylic acid (1R,4S)-4-Aminocyclopent-2-enecarboxylic acid 134003-04-6 C6H9NO2
(S)-3-AMINO-4-(4-NITROPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(4-NITROPHENYL)BUTANOIC ACID HYDROCHLORIDE 270062-87-8 C10H12N2O4
BOC-(R)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID 269726-83-2 C16H20N2O4
DL-Homocystine DL-Homocystine 870-93-9 C8H16N2O4S2
H-TYR(TBU)-OME HCL H-TYR(TBU)-OME HCL 51482-39-4 C14H22ClNO3
2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER 2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER 184174-80-9 C9H11NO2S
H-SER-OBZL HCL H-SER-OBZL HCL 1738-72-3 C10H13NO3
BOC-D-TRP(FOR)-OH BOC-D-TRP(FOR)-OH 64905-10-8 C17H20N2O5
N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE N-CARBOBENZYLOXY-S-PHENYL-L-CYSTEINE 82611-65-2 C17H17NO4S
BOC-(S)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-CHLORO-PHENYL)-BUTYRIC ACID 270596-39-9 C15H20ClNO4
FMOC-7-AMINO-HEPTANOIC ACID FMOC-7-AMINO-HEPTANOIC ACID 127582-76-7 C22H25NO4
N-Acetyl-DL-aspartic acid N-Acetyl-DL-aspartic acid 2545-40-6 C6H9NO5
3-AMINO-2,4,5-TRIFLUOROBENZOIC ACID 3-AMINO-2,4,5-TRIFLUOROBENZOIC ACID 119385-80-7 C7H4F3NO2
H-PHE-NHNH2 H-PHE-NHNH2 52386-52-4 C9H13N3O
3-AMINO-4-PYRIDAZINECARBOXYLIC ACID 3-AMINO-4-PYRIDAZINECARBOXYLIC ACID 21141-03-7 C5H5N3O2
3-AMINO-4-(TRIFLUOROMETHYL)BENZOIC ACID 3-AMINO-4-(TRIFLUOROMETHYL)BENZOIC ACID 125483-00-3 C8H6F3NO2
Thiamphenicol glycinate hydrochloride Thiamphenicol glycinate hydrochloride 2611-61-2 C14H18Cl2N2O6S.ClH
Methotrexate disodium salt Methotrexate disodium salt 7413-34-5 C20H23N8NaO5
N-FORMYL-L-ALANINE N-FORMYL-L-ALANINE 10512-86-4 C4H7NO3
Fmoc-Lys(Ddiv)-OH Fmoc-Lys(Ddiv)-OH 204777-78-6 C34H42N2O6
ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE ETHYL 5-AMINOBENZOFURAN-2-CARBOXYLATE 174775-48-5 C11H11NO3
H-D-TYR(TBU)-OH H-D-TYR(TBU)-OH 186698-58-8 C13H19NO3
4-BORONO-DL-PHENYLALANINE B10 ENRICHED 4-BORONO-DL-PHENYLALANINE B10 ENRICHED 90580-64-6 C9H12BNO4
H-DL-2-NAL-OH H-DL-2-NAL-OH 14108-60-2 C13H13NO2
3-(2-NAPHTHYL)-L-ALANINE HYDROCHLORIDE 3-(2-NAPHTHYL)-L-ALANINE HYDROCHLORIDE 122745-12-4 C13H14ClNO2
FMOC-PRO-OL FMOC-PRO-OL 148625-77-8 C20H21NO3
FMOC-(S)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(3-CYANO-PHENYL)-BUTYRIC ACID 270065-87-7 C26H22N2O4
H-NVA-OME HCL H-NVA-OME HCL 56558-30-6 C6H14ClNO2
2-AMINO-2-PHENYLBUTYRIC ACID 2-AMINO-2-PHENYLBUTYRIC ACID 5438-07-3 C10H13NO2
Brivanib Brivanib 649735-46-6 C19H19FN4O3
Boc-(R)-3-Amino-3-(4-methylphenyl)propionic acid Boc-(R)-3-Amino-3-(4-methylphenyl)propionic acid 479064-97-6 C15H21NO4
N-2-NITROPHENYLSULFENYL-L-ALANINE DICYCLOHEXYLAMMONIUM SALT N-2-NITROPHENYLSULFENYL-L-ALANINE DICYCLOHEXYLAMMONIUM SALT 7675-46-9 C21H33N3O4S
Z-PRO-OSU Z-PRO-OSU 3397-33-9 C17H18N2O6
H-D-TYR(BZL)-OH H-D-TYR(BZL)-OH 65733-15-5 C16H17NO3
(S)-3-AMINO-4-(2-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(2-CYANOPHENYL)BUTANOIC ACID HYDROCHLORIDE 270065-82-2 C11H12N2O2
(R)-(+)-alpha-[(3-Methoxy-1-methyl-3-oxo-1-propenyl)amino]-1,4-cyclohexadiene-1-acetic acid sodium salt (R)-(+)-alpha-[(3-Methoxy-1-methyl-3-oxo-1-propenyl)amino]-1,4-cyclohexadiene-1-acetic acid sodium salt 26774-89-0 C13H18NNaO4
Creatine phosphate disodium salt Creatine phosphate disodium salt 922-32-7 C4H11N3NaO5P
2-(Boc-aminomethyl)phenylacetic acid 2-(Boc-aminomethyl)phenylacetic acid 40851-66-9 C14H19NO4
3-FLUORO-DL-VALINE 3-FLUORO-DL-VALINE 43163-94-6 C5H10FNO2
N-Tigloylglycine N-Tigloylglycine 35842-45-6 C7H11NO3
(R)-3-AMINO-4-(2-NAPHTHYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(2-NAPHTHYL)BUTANOIC ACID HYDROCHLORIDE 269398-90-5 C14H15NO2
DL-3-(1-NAPHTHYL)ALANINE DL-3-(1-NAPHTHYL)ALANINE 28095-56-9 C13H13NO2
N-Tosyl-L-alanine 3-indoxyl ester N-Tosyl-L-alanine 3-indoxyl ester 75062-54-3 C18H18N2O4S
BOC-L-BETA-HOMOTRYPTOPHAN BOC-L-BETA-HOMOTRYPTOPHAN 229639-48-9 C17H22N2O4
N-(2,4-DINITROPHENYL)-L-SERINE N-(2,4-DINITROPHENYL)-L-SERINE 1655-64-7 C9H9N3O7
D-Cyclopentylglycine D-Cyclopentylglycine 2521-86-0 C7H13NO2
PTH-METHIONINE PTH-METHIONINE 4370-90-5 C12H14N2OS2
BOC-CYS(4-MEBZL)-OL BOC-CYS(4-MEBZL)-OL 129397-85-9 C16H25NO3S
HexarelinAcetate HexarelinAcetate
N-ISOBUTYRYLGLYCINE N-ISOBUTYRYLGLYCINE 15926-18-8 C6H11NO3
Phosphatidylserine Phosphatidylserine 51446-62-9 C42H82NO10P
BOC-PHG-OSU BOC-PHG-OSU 201152-47-8 C17H20N2O6
Fmoc-Phe(4-Cl)-Wang resin Fmoc-Phe(4-Cl)-Wang resin
3-AZIDO-L-ALANINE 3-AZIDO-L-ALANINE 105661-40-3
N-Benzyloxycarbonylglycine N-carboxylic anhydride N-Benzyloxycarbonylglycine N-carboxylic anhydride 159396-61-9 C11H9NO5
GLYCINE-2-13C GLYCINE-2-13C 20220-62-6 C2H5NO2
6-CHLOROBENZO[D]OXAZOL-2-AMINE 6-CHLOROBENZO[D]OXAZOL-2-AMINE 52112-68-2 C7H5ClN2O
3-AMINO-2,2-DIMETHYL-PROPIONIC ACID ETHYL ESTER HYDROCHLORIDE 3-AMINO-2,2-DIMETHYL-PROPIONIC ACID ETHYL ESTER HYDROCHLORIDE 80253-38-9 C7H15NO2.ClH
2-AMINOHEPTANOIC ACID 2-AMINOHEPTANOIC ACID 1115-90-8 C7H15NO2
(R)-2-amino-2-methyl-dec-6-enoic acid (R)-2-amino-2-methyl-dec-6-enoic acid 1195967-46-4 C11H21NO2
(S)-N-Fmoc-2-(4'-pentenyl)glycine (S)-N-Fmoc-2-(4'-pentenyl)glycine 856412-22-1 C22H23NO4
(S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-cyanopropanoic acid (S)-2-((((9H-Fluoren-9-yl)Methoxy)carbonyl)aMino)-3-cyanopropanoic acid 127273-06-7 C19H16N2O4
(S)- 2-(7'-octenyl) alanine (S)- 2-(7'-octenyl) alanine 1221256-52-5 C11H21NO2
DL-PHENYLALANINE-CARBOXY-13C DL-PHENYLALANINE-CARBOXY-13C 64193-00-6 C9H11NO2
Fmoc-4-trifluoromethyl-D-homophenylalanine Fmoc-4-trifluoromethyl-D-homophenylalanine 1260604-58-7 C26H22F3NO4
(R)-2-amino-2-(2-methoxyphenyl)acetic acid hydrochloride (R)-2-amino-2-(2-methoxyphenyl)acetic acid hydrochloride 103889-79-8 C9H12ClNO3
Fmoc-2-trifluoromethyl-L-homophenylalanine Fmoc-2-trifluoromethyl-L-homophenylalanine 1260591-46-5 C26H22F3NO4
β-Alanine, N,N-bis(2-hydroxyethyl)-, methyl ester β-Alanine, N,N-bis(2-hydroxyethyl)-, methyl ester 118480-08-3 C8H17NO4
4-chloro-N-(phenylmethyl)- DL-Phenylalanine 4-chloro-N-(phenylmethyl)- DL-Phenylalanine 123760-70-3 C16H16ClNO2
N-(4-isopropyl-1,3-benzothiazol-2-yl)-N-methylglycine N-(4-isopropyl-1,3-benzothiazol-2-yl)-N-methylglycine 1353000-12-0 C13H16N2O2S
3-Cyanophenylalanine 3-Cyanophenylalanine 63999-80-4 C10H10N2O2
Z-GLY-ILE-OH Z-GLY-ILE-OH 20807-11-8 C16H22N2O5
ALPHA-METHYL-L-4-FLUOROPHE ALPHA-METHYL-L-4-FLUOROPHE 130855-57-1 C10H12FNO2
H-GLY-GLY-HIS-GLY-OH H-GLY-GLY-HIS-GLY-OH 128114-56-7 C12H18N6O5
FMOC-D-MEHIS(TRT)-OH FMOC-D-MEHIS(TRT)-OH 1217608-75-7 C41H35N3O4
FMOC-N(HMB)-GLY-OH FMOC-N(HMB)-GLY-OH 148515-78-0 C25H23NO6
Novex 10% Tris-Glycine Mini Gels, WedgeWell format, 10-well Novex 10% Tris-Glycine Mini Gels, WedgeWell format, 10-well
Fmoc-2-trifluoromethyl-D-homophenylalanine Fmoc-2-trifluoromethyl-D-homophenylalanine 1260614-05-8 C26H22F3NO4
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]acetic acid (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]acetic acid 281655-71-8 C27H32N2O6
FOR-PHE-OME FOR-PHE-OME 2311-21-9 C11H13NO3
3,5-DINITRO-L-TYROSINE MONOHYDRATE 3,5-DINITRO-L-TYROSINE MONOHYDRATE 17360-11-1 C9H9N3O7
FMOC-(S)-3-AMINO-3-(4-BROMO-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(4-BROMO-PHENYL)-PROPIONIC ACID 220497-68-7 C24H20BrNO4
N-Cbz-N-methyl-L-leucine N-Cbz-N-methyl-L-leucine 33099-08-0 C15H21NO4
N-EPSILON-2,4-DNP-L-LYSINE HYDROCHLORIDE N-EPSILON-2,4-DNP-L-LYSINE HYDROCHLORIDE 14401-10-6 C12H17ClN4O6
BOC-D-4-AMINOMETHYLPHENYLALANINE(FMOC) BOC-D-4-AMINOMETHYLPHENYLALANINE(FMOC) 215302-77-5 C30H32N2O6
Z-SER-GLY-OET Z-SER-GLY-OET 4526-93-6 C15H20N2O6
PTH-GLYCINE PTH-GLYCINE 2010-15-3 C9H8N2OS
DL-LYSINE DIHYDROCHLORIDE DL-LYSINE DIHYDROCHLORIDE 617-68-5 C6H16Cl2N2O2
Z-THR-GLY-OET Z-THR-GLY-OET 27482-74-2 C16H22N2O6
(S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid (S)-2-(3-((2-Isopropylthiazol-4-yl)methyl)-3-methylureido)-3-methylbutanoic acid 154212-61-0 C14H23N3O3S
Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate Methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 124605-42-1 C15H21NO5
[N,N-bis[2-[bis(carboxymethyl)amino]ethyl]glycinato(5-)]cuprate(3-) [N,N-bis[2-[bis(carboxymethyl)amino]ethyl]glycinato(5-)]cuprate(3-) 11065-66-0 C14H18CuN3O10
3-Hydroxy-D-phenylalanine 3-Hydroxy-D-phenylalanine 32140-49-1 C9H11NO3
Boc-L-isoleucine methyl ester Boc-L-isoleucine methyl ester 17901-01-8 C12H23NO4
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