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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
H-[15N]VAL-OH H-[15N]VAL-OH 59935-29-4 C5H11NO2
N-Benzyloxycarbonyl-6-aminohexanoic acid N-Benzyloxycarbonyl-6-aminohexanoic acid 1947-00-8 C14H19NO4
FMOC-N-(4-BOC-AMINOBUTYL)-GLYCINE FMOC-N-(4-BOC-AMINOBUTYL)-GLYCINE 171856-09-0 C26H32N2O6
3,4-DEHYDRO-L-PROLINE METHYL ESTER HYDROCHLORIDE 3,4-DEHYDRO-L-PROLINE METHYL ESTER HYDROCHLORIDE 186145-08-4 C6H10ClNO2
Z-GLY-GLY-VAL-OH Z-GLY-GLY-VAL-OH 34152-86-8 C17H23N3O6
[(4-BROMOPHENYL)AMINO]ACETIC ACID [(4-BROMOPHENYL)AMINO]ACETIC ACID 13370-62-2 C8H8BrNO2
BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER BOC-4-OXO-L-PROLINE TERT-BUTYL ESTER 166410-05-5 C14H23NO5
BOC-(R)-3-AMINO-3-(2-CHLORO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(2-CHLORO-PHENYL)-PROPIONIC ACID C14H18ClNO4
N-Boc-N'-benzyloxymethyl-L-histidine N-Boc-N'-benzyloxymethyl-L-histidine 99310-01-7 C19H25N3O5
FMOC-D-HIS(MTT)-OH FMOC-D-HIS(MTT)-OH 200926-19-8 C41H35N3O4
4-AMINO-L-PHENYLALANINE HYDROCHLORIDE HEMIHYDRATE 4-AMINO-L-PHENYLALANINE HYDROCHLORIDE HEMIHYDRATE 24286-13-3 C18H27ClN4O5
FMOC-P-FLUORO-DL-PHE-OH FMOC-P-FLUORO-DL-PHE-OH 264276-42-8 C24H20FNO4
POLY-L-VALINE POLY-L-VALINE 25609-85-2 C5H11NO2
4-OXO-PROLINE 4-OXO-PROLINE 2002-02-0 C5H7NO3
BOC-D-2,4,5-TRIFLUOROPHE BOC-D-2,4,5-TRIFLUOROPHE 486460-09-7 C14H16F3NO4
FMOC-L-2-(5-BROMOTHIENYL)ALANINE FMOC-L-2-(5-BROMOTHIENYL)ALANINE 220497-50-7 C22H18BrNO4S
H-D-THR(TBU)-OME HCL H-D-THR(TBU)-OME HCL 115141-43-0 C9H20ClNO3
H-THR(TBU)-OME HCL H-THR(TBU)-OME HCL 71989-43-0 C9H20ClNO3
FMOC-3,4-DIMETHOXY-L-PHENYLALANINE FMOC-3,4-DIMETHOXY-L-PHENYLALANINE 184962-88-7 C26H25NO6
H-LYS-GLY-OH HCL H-LYS-GLY-OH HCL 40719-58-2 C8H18ClN3O3
FMOC-ALA-ALA-PRO-OH FMOC-ALA-ALA-PRO-OH 161220-53-7 C26H29N3O6
ALANYCARB ALANYCARB 83130-01-2 C17H25N3O4S2
BOC-D-GLN(XAN)-OH BOC-D-GLN(XAN)-OH 99092-88-3 C23H26N2O6
N,S-BIS-FMOC-GLUTATHIONE N,S-BIS-FMOC-GLUTATHIONE 149438-56-2 C40H37N3O10S
BOC-GLU-GLU-LEU-OME BOC-GLU-GLU-LEU-OME 72903-33-4 C22H37N3O10
FMOC-D-ALLO-THR(TBU)-OH FMOC-D-ALLO-THR(TBU)-OH 170643-02-4 C23H27NO5
(2S,4S)-4-METHYLGLUTAMIC ACID (2S,4S)-4-METHYLGLUTAMIC ACID 6141-27-1 C6H11NO4
L-Isoleucine hydrochloride L-Isoleucine hydrochloride 17694-98-3 C6H14ClNO2
BOC-D-LEUCINOL  97 BOC-D-LEUCINOL 97 142121-48-0 C11H23NO3
NEPSILON-FMOC-NALPHA-CBZ-L-LYSINE, 98 NEPSILON-FMOC-NALPHA-CBZ-L-LYSINE, 98 105751-18-6 C29H30N2O6
N(ALPHA)-FMOC-N(EPSILON)-DABCYL-L-LYSINE N(ALPHA)-FMOC-N(EPSILON)-DABCYL-L-LYSINE 146998-27-8 C36H37N5O5
Sodium N-tetradecanoyl-L-alaninate Sodium N-tetradecanoyl-L-alaninate 67395-95-3 C17H32NNaO3
Sodium N-dodecanoyl-L-alaninate Sodium N-dodecanoyl-L-alaninate 55535-58-5 C15H28NNaO3
Sodium N-dodecanoyl-L-phenlyalaninate Sodium N-dodecanoyl-L-phenlyalaninate 37869-82-2 C21H32NNaO3
N-Dodecanoyl-L-phenlyalanine N-Dodecanoyl-L-phenlyalanine 14379-64-7 C21H33NO3
(S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE (S)-1-CBZ-2-HYDROXYMETHYLPYRROLIDINE 6216-63-3 C13H17NO3
H-ALA-AMC H-ALA-AMC 77471-41-1 C13H14N2O3
FMOC-PHE(3-I)-OH FMOC-PHE(3-I)-OH 210282-31-8 C24H20INO4
(R)-N-ACETYL-3,4-DIMETHOXYPHENYLALANINE (R)-N-ACETYL-3,4-DIMETHOXYPHENYLALANINE 33043-37-7 C13H17NO5
DL-N-BENZOYL-2-ISOPROPYLSERINE DL-N-BENZOYL-2-ISOPROPYLSERINE 52421-46-2 C13H17NO4
AC-LYS(Z)-OH AC-LYS(Z)-OH 6367-08-4 C16H22N2O5
N-ALPHA-METHYL-D-VALINE HYDROCHLORIDE N-ALPHA-METHYL-D-VALINE HYDROCHLORIDE 210830-32-3 C6H14ClNO2
H-TYR-OBZL H-TYR-OBZL 52799-86-7 C23H23NO3
N-ME-ALA-OTBU HCL N-ME-ALA-OTBU HCL 103614-40-0 C8H18ClNO2
BOC-N-ME-THR-OH BOC-N-ME-THR-OH 101759-72-2 C10H19NO5
FMOC-BETA-(2-QUINOLYL)-D-ALA-OH FMOC-BETA-(2-QUINOLYL)-D-ALA-OH 214852-58-1 C27H22N2O4
N-BOC-ALPHA-METHYL-L-PROLINE N-BOC-ALPHA-METHYL-L-PROLINE 103336-06-7 C11H19NO4
Z-HYP(TBU)-OH Z-HYP(TBU)-OH 85201-91-8 C17H23NO5
BOC-(S)-3-AMINO-4-(4-TERT-BUTYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(4-TERT-BUTYL-PHENYL)-BUTYRIC ACID 403661-85-8 C19H29NO4
BOC-4-NITRO-L-PHENYLALANINE BOC-4-NITRO-L-PHENYLALANINE 103451-56-5 C14H18N2O6
AC-ALA-PNA AC-ALA-PNA 35978-75-7 C11H13N3O4
PD 166793 PD 166793 199850-67-4 C17H18BrNO4S
3,4-Difluoro-D-phenylalanine 3,4-Difluoro-D-phenylalanine 249648-08-6 C9H9F2NO2
D-2-Thiolhistidine D-2-Thiolhistidine 1195264-93-7 C6H9N3O2S
L-Arginine DL-Malate(2:1) L-Arginine DL-Malate(2:1)
N-Acetyl-L-Hydroxyproline N-Acetyl-L-Hydroxyproline 39966-33-7 C7H10NO4
D-(-)-3-thienylglycine D-(-)-3-thienylglycine 1194-86-1 C6H7NO2S
Ethyl N-[[5-methyl-2-(isopropyl)cyclohexyl]carbonyl]glycinate Ethyl N-[[5-methyl-2-(isopropyl)cyclohexyl]carbonyl]glycinate 39668-74-1 C15H27NO3
1,2,4-triazolyl-3-alanine 1,2,4-triazolyl-3-alanine 10109-05-4 C5H8N4O2
1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester 1-tert-butoxycarbonyl-4-hydroxy-L-proline ethyl ester 37813-30-2 C12H21NO5
2-Methoxy-L-phenylalanine 2-Methoxy-L-phenylalanine 193546-31-5 C10H13NO3
1-Amino-2-ethenylcyclopropanecarboxylicacid 1-Amino-2-ethenylcyclopropanecarboxylicacid 80003-54-9 C6H9NO2
Ethyl 2-(acetylamino)-3-[3,5-diiodo-4-(4-methoxyphenoxy)phenyl]propanoate Ethyl 2-(acetylamino)-3-[3,5-diiodo-4-(4-methoxyphenoxy)phenyl]propanoate 83249-56-3 C20H21I2NO5
N-Acetyl-3-chloro-L-serine methyl ester N-Acetyl-3-chloro-L-serine methyl ester 87333-22-0 C6H10ClNO3
L-Citrulline L-Malate 1:1 L-Citrulline L-Malate 1:1
fmoc-D-2,4-dichlorophenylalanine fmoc-D-2,4-dichlorophenylalanine 352351-61-2 C24H19Cl2NO4
3-(2-Pyrrolyl)-DL-alanine 3-(2-Pyrrolyl)-DL-alanine 3078-36-2 C7H10N2O2
D-4-Bromophenylglycine D-4-Bromophenylglycine C8H8BrNO2
DL-Cyclobutylglycine DL-Cyclobutylglycine 28024-69-3 C6H11NO2
N-BOC-(1R,2R)-(-)-2-AMINO-1-(4-NITROPHE& N-BOC-(1R,2R)-(-)-2-AMINO-1-(4-NITROPHE& 366487-74-3 C14H20N2O6
Ethyl N-(2,3-dichloro-6-aminobenzyl)glcycine Ethyl N-(2,3-dichloro-6-aminobenzyl)glcycine 70406-92-7 C11H14Cl2N2O2
Boc-D-2,4-Dichlorophenylalanine Boc-D-2,4-Dichlorophenylalanine 114873-2-0
(1R,2R)-(-)-2-Amino-1-cyclopentanecarboxylic acid (1R,2R)-(-)-2-Amino-1-cyclopentanecarboxylic acid 136315-77-0 C6H11NO2
1-Methyl-5-oxo-D-proline methyl ester 1-Methyl-5-oxo-D-proline methyl ester 122742-14-7 C7H11NO3
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)- (9CI) Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, ethyl ester, (1R,2S)- (9CI) 746657-36-3 C8H13NO2
DL-METHIONINOL DL-METHIONINOL 502-83-0 C5H13NOS
D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) D-Proline, 4-hydroxy-, methyl ester, (4S)- (9CI) 178962-09-9 C6H11NO3
Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, (1R,2S)- (9CI) Cyclopropanecarboxylic acid, 1-amino-2-ethenyl-, (1R,2S)- (9CI) 159700-58-0 C6H9NO2
N-alpha-Methyl-L-lysinehydrochloride N-alpha-Methyl-L-lysinehydrochloride 7431-89-2 C7H16N2O2
D-2,5-Dichlorophenylalanine D-2,5-Dichlorophenylalanine 718596-54-4 C9H9Cl2NO2
D-2-(5-Bromothienyl)alanine D-2-(5-Bromothienyl)alanine 264903-54-0 C7H8BrNO2S
DL-2-Furylalanine DL-2-Furylalanine 4066-39-1 C7H9NO3
(S)-2-CBZ-AMINO-BUTANE-1,4-DIOL
(S)-2-CBZ-AMINO-BUTANE-1,4-DIOL 118219-23-1 C12H17NO4
(S)-N-[4'-BENZYL)PIPERIDINO]PROLINE
(S)-N-[4'-BENZYL)PIPERIDINO]PROLINE 669713-67-1 C17H24N2O2
1-N-BENZYL-PROLINE
1-N-BENZYL-PROLINE 60169-72-4 C12H15NO2
L-4'-TETRAHYDROPYRANYLGLYCINE
L-4'-TETRAHYDROPYRANYLGLYCINE 811842-25-8 C7H13NO3
N-Acetyl-S-(3-carboxy-1-methylpropyl)-L-cysteine N-Acetyl-S-(3-carboxy-1-methylpropyl)-L-cysteine 33164-65-7 C9H15NO5S
Carbobenzoxy-D,L-tryptophanamide Carbobenzoxy-D,L-tryptophanamide 27018-75-3 C19H19N3O3
Fmoc-Lys(Trt)-OH Fmoc-Lys(Trt)-OH 719892-61-2 C40H38N2O4
FMOC-ARG(MTR)-OPFP FMOC-ARG(MTR)-OPFP 130397-19-2 C37H35F5N4O7S
S-SULFO-L-CYSTEINE SODIUM SALT S-SULFO-L-CYSTEINE SODIUM SALT 1637-71-4 C3H7NO5S2
GLYCINE N-PENTYL ESTER HYDROCHLORIDE GLYCINE N-PENTYL ESTER HYDROCHLORIDE 203302-88-9 C7H16ClNO2
NALPHA-FMOC-L-THREONINE TERT-BUTYL ESTER NALPHA-FMOC-L-THREONINE TERT-BUTYL ESTER 120791-76-6 C23H27NO5
S,N-diacetylcysteine monoethyl ester S,N-diacetylcysteine monoethyl ester 19547-89-8 C9H15NO4S
D-CYSTEINE(MBZL)-OH D-CYSTEINE(MBZL)-OH 127348-02-1 C11H15NO2S
Methyl 2-Amino-6-nitrobenzoate Methyl 2-Amino-6-nitrobenzoate 57113-89-0 C8H8N2O4
FMOC-GLU(O-2-PHIPR)-OH FMOC-GLU(O-2-PHIPR)-OH 200616-39-3 C29H29NO6
3-(N-Methylamino)-D-alanine 3-(N-Methylamino)-D-alanine 20790-78-7 C4H10N2O2
N-Boc-(S)-2-amino-3-benzyloxy-1-propanol N-Boc-(S)-2-amino-3-benzyloxy-1-propanol 79069-15-1 C15H23NO4
FMOC-TYR(PO3(MDPSE)2)-OH FMOC-TYR(PO3(MDPSE)2)-OH 158817-11-9 C54H54NO8PSi2
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