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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
Boc-D-Ser-Oipr Boc-D-Ser-Oipr 1253690-13-9 C11H21NO5
(R)-DiMethyl pyrrolidine-1,2-dicarboxylate (R)-DiMethyl pyrrolidine-1,2-dicarboxylate 374077-91-5 C8H13NO4
N-Hexadecanoyl-D-alanine sodiuM salt N-Hexadecanoyl-D-alanine sodiuM salt C19H36NNaO3
N-Hexadecanoyl-D-valine N-Hexadecanoyl-D-valine 132869-86-4 C21H41NO3
N-Octadecanoyl-L-phenylalanine sodiuM salt N-Octadecanoyl-L-phenylalanine sodiuM salt 58725-35-2 C27H44NNaO3
N-Methyl-N-[(3R)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]glycine N-Methyl-N-[(3R)-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]glycine 372198-97-5 C19H20F3NO3
trans-N-Boc-4-[3-(trifluoroMethyl)benzyl]-L-proline, 95% trans-N-Boc-4-[3-(trifluoroMethyl)benzyl]-L-proline, 95% C18H22F3NO4
trans-4-(4-Nitrobenzyl)-L-proline hydrochloride, 95% trans-4-(4-Nitrobenzyl)-L-proline hydrochloride, 95% C12H15ClN2O4
trans-4-(4-Methylbenzyl)-L-proline hydrochloride, 95% trans-4-(4-Methylbenzyl)-L-proline hydrochloride, 95% C13H18ClNO2
trans-4-(3-Phenyl-n-propyl)-L-proline hydrochloride, 95% trans-4-(3-Phenyl-n-propyl)-L-proline hydrochloride, 95% C14H20ClNO2
3-Ethoxy-2,6-difluoro-DL-phenylalanine, 97% 3-Ethoxy-2,6-difluoro-DL-phenylalanine, 97% 1260007-97-3 C11H13F2NO3
(S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone (S)-(-)-4-Benzyl-5,5-dimethyl-2-oxazolidinone 168297-85-6 C12H15NO2
N-CARBOBENZOXY-L-TYROSINE DICYCLOHEXYLAMINE SALT N-CARBOBENZOXY-L-TYROSINE DICYCLOHEXYLAMINE SALT 7278-35-5 C29H40N2O5
D-2-AMINO-4-BROMO-4-PENTENOIC ACID D-2-AMINO-4-BROMO-4-PENTENOIC ACID 264903-49-3 C5H8BrNO2
3-AMINO-4-HYDROXYBENZOIC ACID 3-AMINO-4-HYDROXYBENZOIC ACID 7450-57-9 C7H9N3O2
ACETYLCYSTEINE IMPURITY D ACETYLCYSTEINE IMPURITY D C5H9NO3S
HOMOPHENYLALANINE, L-(RG) HOMOPHENYLALANINE, L-(RG)
L-HISTIDINE ALPHA KETOGLUTARATE(2:1) L-HISTIDINE ALPHA KETOGLUTARATE(2:1)
DL-Histidine·HCl DL-Histidine·HCl
ethyl L-leucinate ethyl L-leucinate 2743-60-4 C8H17NO2
DL-lysine hydrochloride DL-lysine hydrochloride 22834-80-6 C6H15ClN2O2
calcium DL-aspartate calcium DL-aspartate 10389-10-3 C4H5CaNO4
3-fluoro-D-(2-2H)alanine 3-fluoro-D-(2-2H)alanine 35523-45-6 C3H8FNO2
disodium N-(1-oxooctadecyl)-L-glutamate disodium N-(1-oxooctadecyl)-L-glutamate 38079-62-8 C23H41NNa2O5
L-(2-Aminoethoxyvinyl)glycine hydrochloride L-(2-Aminoethoxyvinyl)glycine hydrochloride C6H13ClN2O3
p-Tosyl-L-phenylalanine chloromethyl ketone p-Tosyl-L-phenylalanine chloromethyl ketone
D-Isoleucyl-L-propyl-L-arginine p-nitroanilide hydrochloride D-Isoleucyl-L-propyl-L-arginine p-nitroanilide hydrochloride C21H36ClN7O4
N-CBZ-glycyl-L-prolyl-L-arginine-4-nitroanilide hydrochloride N-CBZ-glycyl-L-prolyl-L-arginine-4-nitroanilide hydrochloride C27H35ClN8O7
N-CBZ-L-aspartic acid-4-t-butyl ester dicyclohexylammonium salt N-CBZ-L-aspartic acid-4-t-butyl ester dicyclohexylammonium salt C28H44N2O6
N-CBZ-L-leucylglycylglycine N-CBZ-L-leucylglycylglycine C18H25N3O6
γ-methylproline γ-methylproline C6H11NO2
CHOLESTERYL/BEHENYL/OCTYLDODECYL LAUROYL GLUTAMATE CHOLESTERYL/BEHENYL/OCTYLDODECYL LAUROYL GLUTAMATE C86H159NO5
METHYLSILANOL HYDROXYPROLINE ASPARTATE METHYLSILANOL HYDROXYPROLINE ASPARTATE C10H20N2O7Si
STEAROYL LEUCINE STEAROYL LEUCINE 14379-43-2 C24H47NO3
ETHYL ASPARTATE ETHYL ASPARTATE 7361-28-6 C6H11NO4
N-BENZYLALANINE METHYL ESTER N-BENZYLALANINE METHYL ESTER 159721-22-9 C11H15NO2
L-CitrullineAlphaKetoglutarate L-CitrullineAlphaKetoglutarate C11H19N3O8
Benzoic acid, 2-amino-3,4-difluoro-, methyl ester (9CI) Benzoic acid, 2-amino-3,4-difluoro-, methyl ester (9CI) 170108-07-3 C8H7F2NO2
Benzoic acid, 4-amino-3-ethoxy-, ethyl ester (9CI) Benzoic acid, 4-amino-3-ethoxy-, ethyl ester (9CI) 342044-64-8 C11H15NO3
L-2,5-Dichlorophenylalanine L-2,5-Dichlorophenylalanine 754971-91-0 C9H9Cl2NO2
D-4-Isopropylphenylalanine D-4-Isopropylphenylalanine 755724-85-7 C12H17NO2
Sodium lauroylglutamate Sodium lauroylglutamate C17H29NNa2O5
Boc-Glu-OMe(OMe) Boc-Glu-OMe(OMe)
Manganese Methionine Manganese Methionine C10H20MnN2O4S2
DL-Serine methyl ester HCl DL-Serine methyl ester HCl C4H10ClNO3
DL-N-AcetylhoMocysteine thiolactone DL-N-AcetylhoMocysteine thiolactone C6H9NO2S
S-(+)-p-Chlorophenylglycine S-(+)-p-Chlorophenylglycine C8H8ClNO2
Glycine, N-(carboxymethyl)-N-2-(carboxymethyl)aminoethyl-, trisodium salt Glycine, N-(carboxymethyl)-N-2-(carboxymethyl)aminoethyl-, trisodium salt 19019-43-3 C8H14N2O6.3Na
BENDAZACLYSINE BENDAZACLYSINE 82576-52-1 C22H28N4O5
methyl-(methylcarbamoylmethyl)azanium methyl-(methylcarbamoylmethyl)azanium 44565-47-1 C4H10N2O
PHENYLSERINE PHENYLSERINE 50897-27-3 C9H11NO3
SELENOMETHIONINE, L-(+)-(RG) SELENOMETHIONINE, L-(+)-(RG)
N.P-Toluenesulfonyl-L-alanine
N.P-Toluenesulfonyl-L-alanine C10H13NO4S
3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,1-amino-,1,1-dimethylethylester 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,1-amino-,1,1-dimethylethylester 489438-95-1 C10H18N2O2
4-Amino-1-cyclohexene-1-carboxylic acid 4-Amino-1-cyclohexene-1-carboxylic acid 13372-08-2 C7H11NO2
1H-Benzimidazole-2-carboxylicacid,5-amino-,ethylester(9CI) 1H-Benzimidazole-2-carboxylicacid,5-amino-,ethylester(9CI) 294174-58-6 C10H11N3O2
Sydnogluton Sydnogluton 153216-47-8 C51H62Cl2F2N7O7
L-SERINE-15N L-SERINE-15N 59935-32-9 C3H715NO3
L-Tryptophan-α-15N L-Tryptophan-α-15N (C8H5NH)CH2CH(*NH2)COOH
H-β-(2-Thienyl)-L-Ala-OH hydrochloride H-β-(2-Thienyl)-L-Ala-OH hydrochloride
(E)-N-(3''-PHENYLPROPYL-ALPHA-CYANO-3'-5'-DIISOPROPYL-4'-HYDROXYCINNAMAMIDE) (E)-N-(3''-PHENYLPROPYL-ALPHA-CYANO-3'-5'-DIISOPROPYL-4'-HYDROXYCINNAMAMIDE) C25H30N2O2
MOLYBDENUM ASPARTATE MOLYBDENUM ASPARTATE C12H15Mo2N3O12
N-(6-Ethylthieno[2,3-d]pyrimidin-4-yl)glycine N-(6-Ethylthieno[2,3-d]pyrimidin-4-yl)glycine 313534-29-1 C10H11N3O2S
benzyl chloroformate benzyl chloroformate 94274-21-2 C8H7ClO2
N-BSMOC-L-PROLINE N-BSMOC-L-PROLINE C15H15NO6S
N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid 1,5-diethyl ester 146943-43-3 C24H29N5O6
N-alpha-Benzyl-L-alanine  methyl  ester N-alpha-Benzyl-L-alanine methyl ester 31022-10-3 C11H15NO2
Boc-D-beta-Homo-Ala Boc-D-beta-Homo-Ala
D-2,6-Dichlorophenylalanine D-2,6-Dichlorophenylalanine C9H9Cl2NO2
Fmoc-L-3-AMP Fmoc-L-3-AMP
L-2,4-Difluorophenylalanine L-2,4-Difluorophenylalanine C9H9F2NO2
(R)-N-Acetyl-5-Chloro-Trp-OMe (R)-N-Acetyl-5-Chloro-Trp-OMe 114872-81-0 C14H15ClN2O3
Cbz-N-Methyl-D-aspartic acid Cbz-N-Methyl-D-aspartic acid C13H15NO6
Fmoc-L-2,4,6-trimethylphenylalanine Fmoc-L-2,4,6-trimethylphenylalanine C27H27NO4
DL-4-Hydroxyphenylglycine methyl ester hydrochloride DL-4-Hydroxyphenylglycine methyl ester hydrochloride 56405-21-1 C9H11NO3
Fmoc-Hyp-OBz Fmoc-Hyp-OBz 439290-35-4 C27H25NO5
1-Methylprrolidine-2-carboxylic acid hydrochloride 1-Methylprrolidine-2-carboxylic acid hydrochloride 30727-22-1 C6H12ClNO2
N-Methyl-L-glutamine N-Methyl-L-glutamine C6H12N2O3
N-Acetyl-DL-serine-15N N-Acetyl-DL-serine-15N 1012312-92-3 C5H9NO4
N-(Phenylsulfonyl)glycine Methyl Ester N-(Phenylsulfonyl)glycine Methyl Ester 69398-48-7 C9H11NO4S
(+/-)-3-oxetanylglycine methyl ester (+/-)-3-oxetanylglycine methyl ester 394653-40-8 C6H11NO3
2,6-Dihydroxyphenyla 2,6-Dihydroxyphenyla
L-Lysine S-Carboxyme L-Lysine S-Carboxyme
β-hydroxyglutamic ac β-hydroxyglutamic ac
H-D-N-Me-Leu-OH H-D-N-Me-Leu-OH
L-Hyp-obzl·TosoH L-Hyp-obzl·TosoH
2-Amino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid hydrochloride 2-Amino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid hydrochloride C10H14ClNO4
Boc-D-Pyr-OBzl Boc-D-Pyr-OBzl 400626-71-3 C17H21NO5
2-(diethoxyMethyl)-5,6-difluoro-1H-benzo[d]iMidazole 2-(diethoxyMethyl)-5,6-difluoro-1H-benzo[d]iMidazole 958863-36-0 C12H14F2N2O2
BOC-Glu(OME)2 BOC-Glu(OME)2
trans-N-Boc-4-(2-propynyl)-L-proline, 95% trans-N-Boc-4-(2-propynyl)-L-proline, 95% C13H19NO4
trans-N-Boc-4-[2-(trifluoroMethyl)benzyl]-L-proline, 95% trans-N-Boc-4-[2-(trifluoroMethyl)benzyl]-L-proline, 95% C18H22F3NO4
4-Fluoro-3,5-diMethyl-DL-phenylalanine, JRD, 97% 4-Fluoro-3,5-diMethyl-DL-phenylalanine, JRD, 97%
N-Butadecanoyl-D-phenylalanine sodiuM salt N-Butadecanoyl-D-phenylalanine sodiuM salt
N-Butadecanoyl-L-phenylglycine N-Butadecanoyl-L-phenylglycine 753018-30-3 C22H35NO3
N-Octadecanoyl-D-phenylalanine sodiuM salt N-Octadecanoyl-D-phenylalanine sodiuM salt C27H44NNaO3
N-Octadecanoyl-L-alanine N-Octadecanoyl-L-alanine 14246-60-7 C21H41NO3
(S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid (S)-2-((Methoxycarbonyl)aMino)-3-Methylbutanoic acid 74761-42-5 C7H13NO4
N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester N-(2'-C-Methyl-6-O-Methyl-P-1-naphthalenyl-5'-guanylyl)-L-alanine 2,2-diMethylpropyl ester 1234490-83-5 C30H39N6O9P
N-Methyl-N-pentyl-beta-alanine methyl ester N-Methyl-N-pentyl-beta-alanine methyl ester 744266-99-7 C10H21NO2
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