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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
CBZ-S-Phenyl-L-cysteine CBZ-S-Phenyl-L-cysteine 159453-24-4 C17H17NO4S
D(-)-Phenylglycinamide D(-)-Phenylglycinamide 6485-67-2 C8H10N2O
BOC-D-SER-OME BOC-D-SER-OME 95715-85-8 C9H17NO5
Boc-N-methyl-L-phenylalanine Boc-N-methyl-L-phenylalanine 37553-65-4 C15H21NO4
GLYCYL-L-THREONINE GLYCYL-L-THREONINE 7093-70-1 C6H12N2O4
L-Ornithine L-aspartate salt L-Ornithine L-aspartate salt 3230-94-2 C5H12N2O2.C4H7NO4
Methyl L-ornithine dihydrochloride Methyl L-ornithine dihydrochloride 40216-82-8 C6H15ClN2O2
N-Carbobenzyloxy-L-valine N-Carbobenzyloxy-L-valine 1149-26-4 C13H17NO4
L-ALLO-ISOLEUCINE L-ALLO-ISOLEUCINE 1509-34-8 C6H13NO2
Fmoc-Dap(Alloc)-OH Fmoc-Dap(Alloc)-OH 188970-92-5 C22H22N2O6
BOC-PHE-OME BOC-PHE-OME 51987-73-6 C15H21NO4
Methyl L-tyrosinate Methyl L-tyrosinate 1080-06-4 C10H13NO3
FMOC-LYS(BIOTIN)-OH FMOC-LYS(BIOTIN)-OH 146987-10-2 C31H38N4O6S
Ethyl 2-aminothiophene-3-carboxylate Ethyl 2-aminothiophene-3-carboxylate 31891-06-2 C7H9NO2S
L-Valine methyl ester hydrochloride L-Valine methyl ester hydrochloride 6306-52-1 C6H13NO2.ClH
3-Hydroxy-N-methyl-3-phenyl-propylamine 3-Hydroxy-N-methyl-3-phenyl-propylamine 42142-52-9 C10H15NO
N'-Nitro-L-arginine-methyl ester hydrochloride N'-Nitro-L-arginine-methyl ester hydrochloride 51298-62-5 C7H16ClN5O4
Boc-Asp-OtBu Boc-Asp-OtBu 34582-32-6 C13H23NO6
L-Cyclohexylalanine L-Cyclohexylalanine 27527-05-5 C9H17NO2
N-Boc-L-alaninol N-Boc-L-alaninol 79069-13-9 C8H17NO3
Boc-Tyr(Me)-OH Boc-Tyr(Me)-OH 53267-93-9 C15H21NO5
Boc-(R)-3-Amino-3-(4-chlorophenyl)propionic acid Boc-(R)-3-Amino-3-(4-chlorophenyl)propionic acid 479064-93-2 C14H18ClNO4
DL-Cysteine DL-Cysteine 3374-22-9 C3H7NO2S
4-Aminophenylacetic acid 4-Aminophenylacetic acid 1197-55-3 C8H9NO2
D-Aspartic acid D-Aspartic acid 1783-96-6 C4H7NO4
5-AMINOVALERIC ACID HYDROCHLORIDE 5-AMINOVALERIC ACID HYDROCHLORIDE 627-95-2 C5H12ClNO2
L-beta-Homoglutamic acid hydrochloride L-beta-Homoglutamic acid hydrochloride 61884-74-0 C6H12ClNO4
Cbz-D-Phenylalaninol Cbz-D-Phenylalaninol 58917-85-4 C17H19NO3
Ethyl L-methionate hydrochloride Ethyl L-methionate hydrochloride 2899-36-7 C7H16ClNO2S
N-Cbz-L-Serine N-Cbz-L-Serine 1145-80-8 C11H13NO5
4-Fluoro-D-phenylalanine 4-Fluoro-D-phenylalanine 18125-46-7 C9H10FNO2
N-FORMYL-L-LEUCINE N-FORMYL-L-LEUCINE 6113-61-7 C7H13NO3
1-Aminocyclopropanecarboxylic acid 1-Aminocyclopropanecarboxylic acid 22059-21-8 C4H7NO2
N-Boc-D-proline N-Boc-D-proline 37784-17-1 C10H17NO4
L-Cystine hydrochloride L-Cystine hydrochloride 34760-60-6 C6H13ClN2O4S2
(1S,2R)-(-)-cis-1-Amino-2-indanol (1S,2R)-(-)-cis-1-Amino-2-indanol 126456-43-7 C9H11NO
1-Aminocyclobutanecarboxylic acid 1-Aminocyclobutanecarboxylic acid 22264-50-2 C5H9NO2
N5-[[[(2,3-Dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-D-ornithine N5-[[[(2,3-Dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-D-ornithine 200116-81-0 C19H30N4O5S
3,4-Diaminobenzoic acid 3,4-Diaminobenzoic acid 619-05-6 C7H8N2O2
L-Proline benzyl ester hydrochloride L-Proline benzyl ester hydrochloride 16652-71-4 C12H16ClNO2
BIS(2-METHOXYETHYL)AMINE BIS(2-METHOXYETHYL)AMINE 111-95-5 C6H15NO2
PyBOP PyBOP 128625-52-5 C18H28F6N6OP2
Boc-L-glutamic acid 5-cyclohexyl ester Boc-L-glutamic acid 5-cyclohexyl ester 73821-97-3 C16H27NO6
HEXAFLUORO-DL-VALINE HEXAFLUORO-DL-VALINE 16063-80-2 C5H5F6NO2
DL-O-Phosphoserine DL-O-Phosphoserine 17885-08-4 C3H8NO6P
D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL D-(-)-THREO-2-AMINO-1-(4-NITROPHENYL)-1,3-PROPANEDIOL 716-61-0 C9H12N2O4
Ethyl L-pyroglutamate Ethyl L-pyroglutamate 7149-65-7 C7H11NO3
L-Phenylglycinol L-Phenylglycinol 3182-95-4 C9H13NO
N-ALPHA-BENZOYL-L-HISTIDINE N-ALPHA-BENZOYL-L-HISTIDINE 5354-94-9 C13H13N3O3
Cbz-L-arginine hydrochloride Cbz-L-arginine hydrochloride 56672-63-0 C14H21ClN4O4
TRANS-2-AMINOCYCLOHEXANOL HYDROCHLORIDE TRANS-2-AMINOCYCLOHEXANOL HYDROCHLORIDE 5456-63-3 C6H14ClNO
Methyl L-lysinate dihydrochloride Methyl L-lysinate dihydrochloride 26348-70-9 C7H18Cl2N2O2
H-Lys(Boc)-OH H-Lys(Boc)-OH 2418-95-3 C11H22N2O4
Boc-O-tert-butyl-L-serine dicyclohexylamine salt Boc-O-tert-butyl-L-serine dicyclohexylamine salt 18942-50-2 C24H46N2O5
FMOC-D-NVA-OH FMOC-D-NVA-OH 144701-24-6 C20H21NO4
(R)-(-)-2-(2,5-Dihydrophenyl)glycine (R)-(-)-2-(2,5-Dihydrophenyl)glycine 26774-88-9 C8H11NO2
(2R,3S)-3-Phenylisoserine hydrochloride (2R,3S)-3-Phenylisoserine hydrochloride 132201-32-2 C9H12ClNO3
Methoxycarbonyl-L-tert-leucine Methoxycarbonyl-L-tert-leucine 162537-11-3 C8H15NO4
BOC-(R)-3-AMINO-4-(2-CHLORO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-CHLORO-PHENYL)-BUTYRIC ACID 218608-93-6 C15H20ClNO4
D-(+)-(2-Chlorophenyl)glycine D-(+)-(2-Chlorophenyl)glycine 86169-24-6 C8H8ClNO2
2-FLUORO-DL-PHENYLALANINE 2-FLUORO-DL-PHENYLALANINE 2629-55-2 C9H10FNO2
Boc-L-glutamic acid 1-tert-butyl ester Boc-L-glutamic acid 1-tert-butyl ester 24277-39-2 C14H25NO6
DL-3-Aminoisobutyric acid DL-3-Aminoisobutyric acid 10569-72-9 C4H9NO2
N-Methyl-L-prolinol N-Methyl-L-prolinol 34381-71-0 C6H13NO
D-2-Amino-4-methylpentanoic acid D-2-Amino-4-methylpentanoic acid 328-38-1 C6H13NO2
N-Acetyl-L-tyrosine N-Acetyl-L-tyrosine 537-55-3 C11H13NO4
BOC-D-3,4-Dichlorophe BOC-D-3,4-Dichlorophe 114873-13-1 C14H17Cl2NO4
FMOC-L-2-Fluorophe FMOC-L-2-Fluorophe 205526-26-7 C24H20FNO4
L-Norleucine L-Norleucine 327-57-1 C6H13NO2
Glycyl-L-glutamine monohydrate Glycyl-L-glutamine monohydrate 13115-71-4 C7H13N3O4
L-Cysteine monohydrochloride L-Cysteine monohydrochloride 52-89-1 C3H8ClNO2S
tert-Butyl carbamate tert-Butyl carbamate 4248-19-5 C5H11NO2
N-Acetyl-DL-glutamic acid N-Acetyl-DL-glutamic acid 5817-08-3 C7H11NO5
N-BOC-L-Arginine hydrochloride N-BOC-L-Arginine hydrochloride 35897-34-8 C11H23ClN4O4
BOC-L-3-Trifluoromethylphe BOC-L-3-Trifluoromethylphe 142995-31-1 C15H18F3NO4
BOC-D-Arg(Tos)-OH BOC-D-Arg(Tos)-OH 61315-61-5 C18H28N4O6S
Methyl L-phenylalaninate hydrochloride Methyl L-phenylalaninate hydrochloride 7524-50-7 C10H14ClNO2
Glycine methyl ester hydrochloride Glycine methyl ester hydrochloride 5680-79-5 C3H8ClNO2
L-Histidine  hydrochloride L-Histidine hydrochloride 645-35-2 C6H10ClN3O2
GLYCYL-L-ALANINE GLYCYL-L-ALANINE 3695-73-6 C5H10N2O3
Z-ASP(OTBU)-OSU Z-ASP(OTBU)-OSU 3338-32-7 C20H24N2O8
(R)-4-Boc-Piperazine-3-carboxylic acid (R)-4-Boc-Piperazine-3-carboxylic acid 278788-60-6 C10H18N2O4
FMOC-(S)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(4-NITRO-PHENYL)-BUTYRIC ACID 270062-88-9 C25H22N2O6
L-Homophenylalanine hydrochloride L-Homophenylalanine hydrochloride 105382-09-0 C10H14ClNO2
Boc-L-Glutamic acid 5-benzylester Boc-L-Glutamic acid 5-benzylester 13574-13-5 C17H23NO6
Boc-D-isoleucine Boc-D-isoleucine 55721-65-8 C11H21NO4
BOC-D-GLU(OTBU)-OH BOC-D-GLU(OTBU)-OH 104719-63-3 C14H25NO6
3-Amino-5-(trifluoromethyl)benzoic acid 3-Amino-5-(trifluoromethyl)benzoic acid 328-68-7 C8H6F3NO2
1-N-Boc-Aminocyclopentanecarboxylic acid 1-N-Boc-Aminocyclopentanecarboxylic acid 35264-09-6 C11H19NO4
Boc-O-(2-bromo-Cbz)-L-Tyrosine Boc-O-(2-bromo-Cbz)-L-Tyrosine 47689-67-8 C22H24BrNO7
TRT-GLY-OH TRT-GLY-OH 5893-05-0 C21H19NO2
Z-GLN(TRT)-OH Z-GLN(TRT)-OH 132388-60-4 C32H30N2O5
L-ASPARTIC ACID POTASSIUM SALT L-ASPARTIC ACID POTASSIUM SALT 1115-63-5 C4H8KNO4
N,N-Dimethylglycine ethyl ester N,N-Dimethylglycine ethyl ester 33229-89-9 C6H13NO2
3-Aminobenzoic acid 3-Aminobenzoic acid 99-05-8 C7H7NO2
(S)-2-Aminobutyramide hydrochloride (S)-2-Aminobutyramide hydrochloride 7682-20-4 C4H11ClN2O
Ademethionine Disulfate Tosylate Ademethionine Disulfate Tosylate 97540-22-2 C22H34N6O16S4
D-Leucinol D-Leucinol 53448-09-2 C6H15NO
(S)-(+)-2-Amino-1-butanol (S)-(+)-2-Amino-1-butanol 5856-62-2 C4H11NO
N-Boc-1-aminocyclobutanecarboxylic acid N-Boc-1-aminocyclobutanecarboxylic acid 120728-10-1 C10H17NO4
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