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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
FMOC-(S)-2-TETRAHYDROISOQUINOLINE ACETIC ACID FMOC-(S)-2-TETRAHYDROISOQUINOLINE ACETIC ACID 270062-99-2 C26H23NO4
H-D-THR(TBU)-OH H-D-THR(TBU)-OH 201274-81-9 C8H17NO3
TYRPHOSTIN A51 TYRPHOSTIN A51 122520-90-5 C13H8N4O3
TRANS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID TRANS-2-AMINO-1-CYCLOHEXANECARBOXYLIC ACID 5691-19-0 C7H13NO2
N-tert-Butoxycarbonyl-N'-benzyloxycarbonyl-L-ornithine N-tert-Butoxycarbonyl-N'-benzyloxycarbonyl-L-ornithine 2480-93-5 C18H26N2O6
BOC-TRANEXAMIC ACID BOC-TRANEXAMIC ACID 27687-14-5 C13H23NO4
BOC-PHE-SER-ARG-AMC ACETATE SALT BOC-PHE-SER-ARG-AMC ACETATE SALT 73554-90-2 C33H43N7O8
3,4-DICHLORO-DL-PHENYLALANINE 3,4-DICHLORO-DL-PHENYLALANINE 5472-67-3 C9H9Cl2NO2
FMOC-(R)-3-AMINO-5-HEXYNOIC ACID FMOC-(R)-3-AMINO-5-HEXYNOIC ACID 332064-94-5 C21H19NO4
Fmoc-Gly-Gly-OH Fmoc-Gly-Gly-OH 35665-38-4 C19H18N2O5
N-Acetyl-D-glutamic acid N-Acetyl-D-glutamic acid 19146-55-5 C7H11NO5
Z-GLY-GLY-LEU-OH Z-GLY-GLY-LEU-OH 13347-77-8 C18H25N3O6
D-PROPARGYLGLYCINE D-PROPARGYLGLYCINE 23235-03-2 C5H7NO2
N-(TERT-BUTOXYCARBONYL)-D-PROLINAL N-(TERT-BUTOXYCARBONYL)-D-PROLINAL 73365-02-3 C10H17NO3
BOC-D-TIC-OH BOC-D-TIC-OH 115962-35-1 C15H19NO4
DMOG DMOG 89464-63-1 C6H9NO5
4-(Boc-amino)-1-(Fmoc-piperidinyl)-4-carboxylic Acid 4-(Boc-amino)-1-(Fmoc-piperidinyl)-4-carboxylic Acid 368866-07-3 C26H30N2O6
FMOC-(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(3-CHLORO-PHENYL)-PROPIONIC ACID 511272-53-0 C24H20ClNO4
BOC-(R)-3-AMINO-3-(2-NITRO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(2-NITRO-PHENYL)-PROPIONIC ACID 501015-23-2 C14H18N2O6
4-AMINO-PYRIDAZINE-3-CARBOXYLIC ACID 4-AMINO-PYRIDAZINE-3-CARBOXYLIC ACID 20865-29-6 C5H5N3O2
N,N'-Bis(benzyloxycarbonyl)-L-cystine N,N'-Bis(benzyloxycarbonyl)-L-cystine 6968-11-2 C22H24N2O8S2
BOC-CYS(BZL)-OL BOC-CYS(BZL)-OL 139428-96-9 C15H23NO3S
H-GLY-PNA H-GLY-PNA 1205-88-5 C8H9N3O3
DIETHYL (BOC-AMINO)MALONATE DIETHYL (BOC-AMINO)MALONATE 102831-44-7 C12H21NO6
BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE BOC-L-LEUCINE N,O-DIMETHYLHYDROXAMIDE 87694-52-8 C12H24N2O4
BOC-(R)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID 765263-36-3 C15H20BrNO4
METHYL 5-AMINO-2-FUROATE METHYL 5-AMINO-2-FUROATE 22600-30-2 C6H7NO3
DABSYL-L-PROLINE DABSYL-L-PROLINE 89131-09-9 C19H22N4O4S
FMOC-HOMOCYS(TRT)-OH FMOC-HOMOCYS(TRT)-OH 167015-23-8 C38H33NO4S
(R)-3-AMINO-4-(4-CHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-CHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 331763-59-8 C10H13Cl2NO2
FMOC-(S)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-BROMO-PHENYL)-BUTYRIC ACID 403661-79-0 C25H22BrNO4
L-PYROGLUTAMIC ACID 4-METHYL-7-COUMARINYLAMIDE HYDRATE L-PYROGLUTAMIC ACID 4-METHYL-7-COUMARINYLAMIDE HYDRATE 66642-36-2 C15H14N2O4
TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE
TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE 142347-81-7 C5H10ClNO3
4-Amino-2-methylquinoline-6-carboxylic acid 4-Amino-2-methylquinoline-6-carboxylic acid 99984-73-3 C11H10N2O2
BOC-SER-OH H2O BOC-SER-OH H2O 204191-40-2 C8H17NO6
H-D-TRP-OBZL HCL H-D-TRP-OBZL HCL 22839-16-3 C18H19ClN2O2
NALPHA,NOMEGA-DICARBOBENZOXY-L-ARGININE NALPHA,NOMEGA-DICARBOBENZOXY-L-ARGININE 53934-75-1 C22H26N4O6
N,N-DIETHYLGLYCINE METHYL ESTER N,N-DIETHYLGLYCINE METHYL ESTER 30280-35-4 C7H15NO2
(R)-3-AMINO-4-(3,4-DIFLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(3,4-DIFLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 269396-58-9 C10H11F2NO2
N,N′-Bis-tert-butoxycarbonylthiourea N,N′-Bis-tert-butoxycarbonylthiourea 145013-05-4 C11H20N2O4S
VINYL ACCA VINYL ACCA 159622-10-3 C11H17NO4
5-AMINO-2-METHOXYBENZOIC ACID 5-AMINO-2-METHOXYBENZOIC ACID 3403-47-2 C8H9NO3
DL-ALLO-ISOLEUCINE DL-ALLO-ISOLEUCINE 3107-04-8 C6H13NO2
DL-CYCLOSERINE DL-CYCLOSERINE 68-39-3 C3H6N2O2
Boc-N-methyl-D-leucine Boc-N-methyl-D-leucine 89536-84-5 C12H23NO4
FMOC-(R)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID FMOC-(R)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID 332064-75-2 C27H25NO4
4-DIMETHYLAMINOBUTYRIC ACID HYDROCHLORIDE 4-DIMETHYLAMINOBUTYRIC ACID HYDROCHLORIDE 69954-66-1 C6H14ClNO2
BZ-DL-ARG-BETANA HCL BZ-DL-ARG-BETANA HCL 913-04-2 C23H26ClN5O2
BOC-ALLO-ILE-OH BOC-ALLO-ILE-OH 35264-07-4 C11H21NO4
N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT N,N-BIS(CARBOXYLATOMETHYL)ALANINE TRISODIUM SALT 164462-16-2 C7H12NNaO6
NG-MONOMETHYL-D-ARGININE MONOACETATE NG-MONOMETHYL-D-ARGININE MONOACETATE 137694-75-8 C9H20N4O4
AC-DL-HIS-OH H2O AC-DL-HIS-OH H2O 213178-97-3 C8H13N3O4
BOC-ARG(Z)-OH BOC-ARG(Z)-OH 51219-18-2 C19H28N4O6
FMOC-(S)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID FMOC-(S)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID 270596-45-7 C27H25NO4
LYS-ARG-PRO-PRO-GLY-PHE-SER-PRO-PHE LYS-ARG-PRO-PRO-GLY-PHE-SER-PRO-PHE 71800-36-7 C50H73N13O11
MEOSUC-ALA-ALA-PRO-VAL-AMC MEOSUC-ALA-ALA-PRO-VAL-AMC 72252-90-5 C31H41N5O9
N-Boc-N'-xanthyl-L-asparagine N-Boc-N'-xanthyl-L-asparagine 65420-40-8 C22H24N2O6
(1R,2S)-1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER (1R,2S)-1-BOC-AMINO-2-VINYLCYCLOPROPANECARBOXYLIC ACID ETHYL ESTER 213316-49-5 C13H21NO4
N-(2-NITROPHENYLSULFENYL)-S-BENZYL-L-CYSTEINE DICYCLOHEXYLAMMONIUM SALT N-(2-NITROPHENYLSULFENYL)-S-BENZYL-L-CYSTEINE DICYCLOHEXYLAMMONIUM SALT 7675-65-2 C28H39N3O4S2
BOC-(R)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID 500789-07-1 C14H18BrNO4
(H-CYS-BETANA)2 (H-CYS-BETANA)2 1259-69-4 C26H26N4O2S2
BOC-(R)-3-AMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID 500788-85-2 C15H21NO5
3,5-DIBROMO-L-TYROSINE HYDRATE 3,5-DIBROMO-L-TYROSINE HYDRATE C9H11Br2NO4
AC-LYS (BOC)-OH AC-LYS (BOC)-OH 23500-04-1 C13H24N2O5
FMOC-D-DAB(Z)-OH FMOC-D-DAB(Z)-OH 387824-79-5 C27H26N2O6
N-BOC-ERYTHRO-L-BETA-METHYLPHENYLALANINE N-BOC-ERYTHRO-L-BETA-METHYLPHENYLALANINE 90731-57-0 C15H21NO4
L-2-AMINO-3-GUANIDINOPROPIONIC ACID HYDROCHLORIDE L-2-AMINO-3-GUANIDINOPROPIONIC ACID HYDROCHLORIDE 1482-99-1 C4H11ClN4O2
(R)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID HYDROCHLORIDE (R)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID HYDROCHLORIDE 270596-35-5 C12H15NO2
L-2-AMINO-5-PHENYL-PENTANOIC ACID L-2-AMINO-5-PHENYL-PENTANOIC ACID 62777-25-7 C11H15NO2
H-D-MET-OET HCL H-D-MET-OET HCL 7512-43-8 C7H16ClNO2S
D-TERT-LEUCINE HYDROCHLORIDE D-TERT-LEUCINE HYDROCHLORIDE 112720-39-5 C6H14ClNO2
H-D-CHA-OH H-D-CHA-OH 58717-02-5 C9H17NO2
AC-ALA-GLN-OH AC-ALA-GLN-OH 121574-43-4 C10H17N3O5
O-ACETYL-L-SERINE O-ACETYL-L-SERINE 5147-00-2 C5H9NO4
BOC-(R)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID BOC-(R)-3-AMINO-(6-PHENYL)-5-HEXENOIC ACID 332064-73-0 C17H23NO4
DL-GLUTAMIC ACID HYDROCHLORIDE DL-GLUTAMIC ACID HYDROCHLORIDE 15767-75-6 C5H10ClNO4
Z-D-PYR-OH Z-D-PYR-OH 78339-57-8 C13H13NO5
H-GLY-MET-OH H-GLY-MET-OH 554-94-9 C7H14N2O3S
FMOC-(S)-3-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID 501015-34-5 C24H19Cl2NO4
CHLOROACETYL-DL-SERINE CHLOROACETYL-DL-SERINE 67206-28-4 C5H8ClNO4
N-(3-Indolylacetyl)-L-isoleucine N-(3-Indolylacetyl)-L-isoleucine 57105-45-0 C16H20N2O3
3,5-Diiodo-DL-tyrosine 3,5-Diiodo-DL-tyrosine 66-02-4 C9H9I2NO3
N-Acetyl-L-thioproline N-Acetyl-L-thioproline 54323-50-1 C6H9NO3S
	L-Citrulline DL-Malate 2:1 L-Citrulline DL-Malate 2:1 54940-97-5 C10H19N3O8
4-AMINO-2-METHYLTHIO-5-THIAZOLECARBOXYLIC ACID METHYL ESTER 4-AMINO-2-METHYLTHIO-5-THIAZOLECARBOXYLIC ACID METHYL ESTER 60093-05-2 C6H8N2O2S2
L-Alanyl-L-leucine L-Alanyl-L-leucine 3303-34-2 C9H18N2O3
FMOC-HIS-OH FMOC-HIS-OH 116611-64-4 C21H19N3O4
H-ALPHA-ME-D-VAL-OH H-ALPHA-ME-D-VAL-OH 53940-82-2 C6H13NO2
DL-CYSTEIC ACID DL-CYSTEIC ACID 3024-83-7 C3H7NO5S
FMOC-D-LYS(MTT)-OH FMOC-D-LYS(MTT)-OH 198544-94-4 C41H40N2O4
L-Leucinamide hydrochloride L-Leucinamide hydrochloride 10466-61-2 C6H15ClN2O
(+)-(1S,3R)-N-FMOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID (+)-(1S,3R)-N-FMOC-3-AMINOCYCLOPENTANECARBOXYLIC ACID 220497-66-5 C21H21NO4
4-Amino-1H-imidazole-2-carboxylic acid 4-Amino-1H-imidazole-2-carboxylic acid 155815-92-2 C4H5N3O2
4-AMINOQUINOLINE-2-CARBOXYLIC ACID 4-AMINOQUINOLINE-2-CARBOXYLIC ACID 157915-66-7 C10H8N2O2
(R)-alpha,alpha-Diphenylmethylprolinol (R)-alpha,alpha-Diphenylmethylprolinol 144119-12-0 C18H21NO
(R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid (R)-2-Acetamido-3-(4-chlorophenyl)propanoic acid 135270-40-5 C11H12ClNO3
DL-3,4-Dimethylphenylalanine DL-3,4-Dimethylphenylalanine 103957-56-8 C11H15NO2
3,5-Difluoro-D-phenylalanine 3,5-Difluoro-D-phenylalanine 266360-63-8 C9H9F2NO2
DL-THREONINE METHYL ESTER HYDROCHLORIDE DL-THREONINE METHYL ESTER HYDROCHLORIDE 62076-66-8 C5H12ClNO3
4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE 4-BIS(2-CHLORETHYL)-AMINO-L-PHENYLALANINE HYDROCHLORIDE 3223-07-2 C13H19Cl3N2O2
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