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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
tert-Butyl L-valinate tert-Butyl L-valinate 13211-31-9 C9H19NO2
Boc-L-aspartic acid 4-benzyl ester Boc-L-aspartic acid 4-benzyl ester 7536-58-5 C16H21NO6
BOC-(S)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 270065-74-2 C16H20F3NO4
L-Alaninol L-Alaninol 2749-11-3 C3H9NO
N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine 82717-96-2 C15H21NO4
(S)-3-Amino-1,2-propanediol (S)-3-Amino-1,2-propanediol 61278-21-5 C3H9NO2
3-Nitro-L-tyrosine 3-Nitro-L-tyrosine 621-44-3 C9H10N2O5
BOC-SER(BZL)-OSU BOC-SER(BZL)-OSU 13650-73-2 C19H24N2O7
2-Amino-2-methyl-3-phenylpropionic acid 2-Amino-2-methyl-3-phenylpropionic acid 1132-26-9 C10H13NO2
DL-Cysteine hydrochloride DL-Cysteine hydrochloride 10318-18-0 C3H8ClNO2S
DL-Isoserine DL-Isoserine 565-71-9 C3H7NO3
N-Cbz-D-Alanine N-Cbz-D-Alanine 26607-51-2 C11H13NO4
L(+)-Homoarginine hydrochloride L(+)-Homoarginine hydrochloride 1483-01-8 C7H17ClN4O2
L-4-Cyanophenylalanine L-4-Cyanophenylalanine 167479-78-9 C10H10N2O2
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 58632-95-4 C13H14N2O3
L-Glutamic acid 5-tert-butyl ester L-Glutamic acid 5-tert-butyl ester 2419-56-9 C9H17NO4
Homo-L-tyrosine, Hydrobromide Homo-L-tyrosine, Hydrobromide 141899-12-9 C10H14BrNO3
Z-D-PHG-OH Z-D-PHG-OH 17609-52-8 C16H15NO4
(R)-N-(tert-Butoxycarbonyl)-2-phenylglycinol (R)-N-(tert-Butoxycarbonyl)-2-phenylglycinol 102089-74-7 C13H19NO3
(S)-(-)-2-(Boc-Amino)-1,4-butanediol (S)-(-)-2-(Boc-Amino)-1,4-butanediol 128427-10-1 C9H19NO4
tert-Butyl sarcosinate hydrochloride tert-Butyl sarcosinate hydrochloride 5616-81-9 C7H15NO2
D-Allylglycine hydrochloride D-Allylglycine hydrochloride 108412-04-0 C5H10ClNO2
Fmoc-3-(2-Naphthyl)-D-alanine Fmoc-3-(2-Naphthyl)-D-alanine 138774-94-4 C28H23NO4
Thymosin α1 Thymosin α1 62304-98-7 C129H215N33O55
Diethyl L-glutamate hydrochloride Diethyl L-glutamate hydrochloride 1118-89-4 C9H18ClNO4
(R)-N-BOC-3-Chlorophenylalanine (R)-N-BOC-3-Chlorophenylalanine 80102-25-6 C14H18ClNO4
BENZOYL-DL-PHENYLALANINE BENZOYL-DL-PHENYLALANINE 2901-76-0 C16H15NO3
L-METHIONINE SULFOXIMINE L-METHIONINE SULFOXIMINE 15985-39-4 C5H12N2O3S
N-Boc-D-Valino N-Boc-D-Valino 106391-87-1 C10H21NO3
(R)-N-Fmoc-Allylglycine (R)-N-Fmoc-Allylglycine 170642-28-1 C20H19NO4
D-Prolinamide D-Prolinamide 62937-45-5 C5H10N2O
D-3-Chlorophenylalanine D-3-Chlorophenylalanine 80126-52-9 C9H10ClNO2
2-Amino-3-nitrobenzoic acid 2-Amino-3-nitrobenzoic acid 606-18-8 C7H6N2O4
FMOC-LYS(FMOC)-OH FMOC-LYS(FMOC)-OH 78081-87-5 C36H34N2O6
BOC-(R)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID 219297-12-8 C15H20N2O6
4-Amino-1-Boc-piperidine 4-Amino-1-Boc-piperidine 87120-72-7 C10H20N2O2
Fmoc-O-(benzylphospho)-L-serine Fmoc-O-(benzylphospho)-L-serine 158171-14-3 C25H24NO8P
DL-ALPHA-AMINOPIMELIC ACID DL-ALPHA-AMINOPIMELIC ACID 627-76-9 C7H13NO4
BOC-D-2-Chlorophe BOC-D-2-Chlorophe 80102-23-4 C14H18ClNO4
(R)-(-)-2-Amino-1-butanol (R)-(-)-2-Amino-1-butanol 5856-63-3 C4H11NO
Fmoc-L-phenylglycine Fmoc-L-phenylglycine 102410-65-1 C23H19NO4
Diisopropanolamine Diisopropanolamine 110-97-4 C6H15NO2
Ethylenediaminetetraacetic acid trisodium salt solution Ethylenediaminetetraacetic acid trisodium salt solution 150-38-9 C10H13N2Na3O8·2H2O
Ethyl L-serinate hydrochloride Ethyl L-serinate hydrochloride 26348-61-8 C5H12ClNO3
N-Methyl-D-aspartic acid N-Methyl-D-aspartic acid 6384-92-5 C5H9NO4
L-Isoleucine tert-butyl ester hydrochloride L-Isoleucine tert-butyl ester hydrochloride 69320-89-4 C10H22ClNO2
Methyl 2-amino-4,5-difluorobenzoate Methyl 2-amino-4,5-difluorobenzoate 207346-42-7 C8H7F2NO2
L-Aspartic acid 4-cyclohexyl ester L-Aspartic acid 4-cyclohexyl ester 112259-66-2 C10H17NO4
Z-DL-ASPARAGINE Z-DL-ASPARAGINE 29880-22-6 C12H14N2O5
3-FLUORO-DL-TYROSINE 3-FLUORO-DL-TYROSINE 403-90-7 C9H10FNO3
4-IODO-D-PHENYLALANINE 4-IODO-D-PHENYLALANINE 62561-75-5 C9H10INO2
Fmoc-L-Lys(Dde)-OH Fmoc-L-Lys(Dde)-OH 150629-67-7 C31H36N2O6
Boc-L-beta-homoisoleucine Boc-L-beta-homoisoleucine 218608-82-3 C12H23NO4
3-Aminomethylbenzoic acid hydrochloride 3-Aminomethylbenzoic acid hydrochloride 876-03-9 C8H10ClNO2
3,3-Diphenyl-D-alanine 3,3-Diphenyl-D-alanine 149597-91-1 C15H15NO2
BOC-MEPHE-OH DCHA BOC-MEPHE-OH DCHA 40163-88-0 C27H44N2O4
L-Leucine benzyl ester p-toluenesulfonate salt L-Leucine benzyl ester p-toluenesulfonate salt 1738-77-8 C20H27NO5S
Fmoc-Phe-OH Fmoc-Phe-OH 35661-40-6 C24H21NO4
FMOC-D-PENTAFLUOROPHENYLALANINE FMOC-D-PENTAFLUOROPHENYLALANINE 198545-85-6 C24H16F5NO4
Cbz-N-methyl-L-phenylalanine Cbz-N-methyl-L-phenylalanine 2899-07-2 C18H19NO4
FMOC-(S)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(4-CHLORO-PHENYL)-BUTYRIC ACID 270596-43-5 C25H22ClNO4
N-Benzylglycine ethyl ester N-Benzylglycine ethyl ester 6436-90-4 C11H15NO2
3-Aminofurazan-4-carboxylic acid 3-Aminofurazan-4-carboxylic acid 78350-50-2 C3H3N3O3
N-(2-CARBOXYPHENYL)GLYCINE N-(2-CARBOXYPHENYL)GLYCINE 612-42-0 C9H9NO4
L-N-[(4'-BOC)PIPERIDINO]PROLINE L-N-[(4'-BOC)PIPERIDINO]PROLINE 221352-39-2 C15H26N2O4
Fmoc-L-beta-homophenylalanine Fmoc-L-beta-homophenylalanine 193954-28-8 C25H23NO4
DL-3-(4-Fluorophenyl)alanine DL-3-(4-Fluorophenyl)alanine 51-65-0 C9H10FNO2
1-Methyl-L-histidine 1-Methyl-L-histidine 332-80-9 C7H11N3O2
Potassium (R)-[(3-ethoxy-1-methyl-3-oxoprop-1-enyl)amino]phenylacetate Potassium (R)-[(3-ethoxy-1-methyl-3-oxoprop-1-enyl)amino]phenylacetate 961-69-3 C14H16KNO4
2-(4-Aminophenyl)ethanol 2-(4-Aminophenyl)ethanol 104-10-9 C8H11NO
S-Carboxymethyl-L-Cysteine S-Carboxymethyl-L-Cysteine 638-23-3 C5H9NO4S
N-Acetyl carnosine N-Acetyl carnosine 56353-15-2 C11H16N4O4
FMOC-ARG(NO2)-OH FMOC-ARG(NO2)-OH 58111-94-7 C21H23N5O6
2-Amino-4-fluorobenzoic acid 2-Amino-4-fluorobenzoic acid 446-32-2 C7H6FNO2
FMOC-L-3-Fluorophe FMOC-L-3-Fluorophe 198560-68-8 C24H20FNO4
(1R,2S)-2-Amino-1,2-diphenylethanol (1R,2S)-2-Amino-1,2-diphenylethanol 23190-16-1 C14H15NO
DL-2-AMINOADIPIC ACID DL-2-AMINOADIPIC ACID 542-32-5 C6H11NO4
BOC-D-4-Chlorophe BOC-D-4-Chlorophe 57292-44-1 C14H18ClNO4
L-Alanine methyl ester hydrochloride L-Alanine methyl ester hydrochloride 2491-20-5 C4H10ClNO2
3-Amino-L-alanine hydrochloride 3-Amino-L-alanine hydrochloride 1482-97-9 C3H9ClN2O2
Boc-L-Pyroglutamic acid methyl ester Boc-L-Pyroglutamic acid methyl ester 108963-96-8 C11H17NO5
L-Aspartic acid dibenzyl ester 4-toluenesulfonate L-Aspartic acid dibenzyl ester 4-toluenesulfonate 2886-33-1 C25H27NO7S
Nalpha-Fmoc-L-tyrosine Nalpha-Fmoc-L-tyrosine 92954-90-0 C24H21NO5
H-ARG-NH2 2HCL H-ARG-NH2 2HCL 14975-30-5 C6H17Cl2N5O
4-Nitroanthranilic acid 4-Nitroanthranilic acid 619-17-0 C7H6N2O4
Z-D-MET-OH Z-D-MET-OH 28862-80-8 C13H17NO4S
BOC-(R)-3-AMINO-4-(2-NAPHTHYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-NAPHTHYL)-BUTYRIC ACID 219297-10-6 C19H23NO4
Fmoc-L-Arg(Pbf)-OH Fmoc-L-Arg(Pbf)-OH 154445-77-9 C34H40N4O7S
L-Alaninamide hydrochloride L-Alaninamide hydrochloride 33208-99-0 C3H9ClN2O
(R)-N-Boc-(4-Pyridyl)alanine (R)-N-Boc-(4-Pyridyl)alanine 37535-58-3 C13H18N2O4
3-Chloro-L-tyrosine 3-Chloro-L-tyrosine 7423-93-0 C9H10ClNO3
2-Acetylamino-propionic acid 2-Acetylamino-propionic acid 1115-69-1 C5H9NO3
H-LEU-PNA H-LEU-PNA 4178-93-2 C12H17N3O3
Fmoc-4-nitro-L-phenylalanine Fmoc-4-nitro-L-phenylalanine 95753-55-2 C24H20N2O6
4-Amino-1-butanol 4-Amino-1-butanol 13325-10-5 C4H11NO
(R)-(-)-2-Amino-1-propanol (R)-(-)-2-Amino-1-propanol 35320-23-1 C3H9NO
Benzyl chloroformate Benzyl chloroformate 501-53-1 C8H7ClO2
(R)-3-Amino-3-phenylpropionic acid hydrochloride (R)-3-Amino-3-phenylpropionic acid hydrochloride 83649-48-3 C9H12ClNO2
Ethyl 3-(pyridin-2-ylamino)propanoate Ethyl 3-(pyridin-2-ylamino)propanoate 103041-38-9 C10H14N2O2
N-CARBOBENZOXY-L-ISOLEUCINE DICYCLOHEXYLAMMONIUM SALT N-CARBOBENZOXY-L-ISOLEUCINE DICYCLOHEXYLAMMONIUM SALT 26699-00-3 C26H42N2O4
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