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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
3,4-Difluoro-D-homophenylalanine 3,4-Difluoro-D-homophenylalanine 1260610-37-4 C10H11F2NO2
N-Fmoc-7-methyl-L-tryptophan N-Fmoc-7-methyl-L-tryptophan 1808268-53-2 C27H24N2O4
L-PHENYLALANINE (2-13C) L-PHENYLALANINE (2-13C) 136056-01-4 C9H11NO2
4-nitro-N-[(phenylmethoxy)carbonyl]- DL-Phenylalanine 4-nitro-N-[(phenylmethoxy)carbonyl]- DL-Phenylalanine 82611-60-7 C17H16N2O6
2-AMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID 2-AMINO-3-(2-METHOXY-PHENYL)-PROPIONIC ACID 22976-68-7 C10H13NO3
Boc-3,5-dichloro-D-homophenylalanine Boc-3,5-dichloro-D-homophenylalanine 1260606-38-9 C15H19Cl2NO4
FMOC-L-3-METHOXYPHENYLALANINE FMOC-L-3-METHOXYPHENYLALANINE 206060-40-4 C25H23NO5
L-Phenylalanine Dehydrogenase (Crude Enzyme) L-Phenylalanine Dehydrogenase (Crude Enzyme)
N-(Methoxycarbonyl)glycine Methyl Ester N-(Methoxycarbonyl)glycine Methyl Ester 70288-73-2 C5H9NO4
Fmoc-2,3-difluoro-D-homophenylalanine Fmoc-2,3-difluoro-D-homophenylalanine 1260618-73-2 C25H21F2NO4
N-Methoxycarbonyl-L-Alanine N-Methoxycarbonyl-L-Alanine
Boc-His(Trt)-Ala-Glu(OtBu)-Gly-OH Boc-His(Trt)-Ala-Glu(OtBu)-Gly-OH 1418291-58-3 C44H54N6O9
AC-D-BPA-OH AC-D-BPA-OH 104504-42-9 C18H17NO4
BOC-L-4-TERT-BUTYL-PHE BOC-L-4-TERT-BUTYL-PHE 143415-62-7 C18H27NO4
2-Amino-N-methyl-acetamide 2-Amino-N-methyl-acetamide 22356-89-4 C3H8N2O
Fmoc-Gly-Arg(Pbf)-OH Fmoc-Gly-Arg(Pbf)-OH 1048377-78-1 C36H43N5O8S
Trityl-L-Phenylalanine diethylammonium salt Trityl-L-Phenylalanine diethylammonium salt 3226-92-4 C28H25NO2.C4H11N
2,4,6-Trifluoro-D-Phenylalanine 2,4,6-Trifluoro-D-Phenylalanine 146277-48-7 C12H17NO2
H-P-FLUORO-DL-PHE-OME HCL H-P-FLUORO-DL-PHE-OME HCL 64282-12-8 C10H13ClFNO2
Fmoc-Cys(STmp)-OH Fmoc-Cys(STmp)-OH 1403834-74-1 C27H27NO7S2
D-3-THIENYLALANINE D-3-THIENYLALANINE 152612-26-5 C7H9NO2S
N-Boc-D-4-Boc-aminomethylPhenylalanine N-Boc-D-4-Boc-aminomethylPhenylalanine 1241676-26-5 C20H30N2O6
N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-L-PHENYLALANINE DICYCLOHEXYLAMINE N-ALPHA-BENZYLOXYCARBONYL-N-ALPHA-METHYL-L-PHENYLALANINE DICYCLOHEXYLAMINE 2899-08-3 C30H42N2O4
2-Trifluoromethyl-D-homophenylalanine 2-Trifluoromethyl-D-homophenylalanine 1260614-29-6 C11H12F3NO2
AC-LEU-GLY-OH AC-LEU-GLY-OH 4033-42-5 C10H18N2O4
N,N-Dimethyl-L-phenylalanine N,N-Dimethyl-L-phenylalanine 17469-89-5 C11H15NO2
(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(2,5-DIFLUOROPHENYL)PROPANOIC ACID (2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]-3-(2,5-DIFLUOROPHENYL)PROPANOIC ACID 261380-31-8 C14H17F2NO4
Alanine Racemase (Crude Enzyme) Alanine Racemase (Crude Enzyme)
Fmoc-Ile-Aib-OH Fmoc-Ile-Aib-OH 2171139-20-9 C25H30N2O5
N-TRIFLUOROACETYL-L-PHENYLALANINE N-TRIFLUOROACETYL-L-PHENYLALANINE 350-09-4 C11H10F3NO3
N-ACETYL-N-PHENYLGLYCINE N-ACETYL-N-PHENYLGLYCINE 579-98-6 C10H11NO3
sodium (Z)-N-methyl-N-(1-oxo-9-octadecenyl)aminoacetate sodium (Z)-N-methyl-N-(1-oxo-9-octadecenyl)aminoacetate 14351-62-3 C21H38NNaO3
DL-4-Methoxyphenylglycine DL-4-Methoxyphenylglycine 22094-69-5 C9H11NO3
Z-L-Phenylalanine N-carboxyanhydride Z-L-Phenylalanine N-carboxyanhydride 25613-60-9 C18H15NO5
BOC-ALA-GLY-OH BOC-ALA-GLY-OH 28782-78-7 C10H18N2O5
BOC-D-PHE-OME BOC-D-PHE-OME 77119-84-7 C15H21NO4
(AMINOCARBONYL)(METHYL)AMINO]ACETIC ACID (AMINOCARBONYL)(METHYL)AMINO]ACETIC ACID 30565-25-4 C4H8N2O3
L-PHENYL-D5-ALANINE-N-T-BOC L-PHENYL-D5-ALANINE-N-T-BOC 121695-40-7 C14H14D5NO4
BOC-D-2,4-DIMETHYLPHE BOC-D-2,4-DIMETHYLPHE 791625-59-7 C16H23NO4
ethyl 2-(propylamino)acetate ethyl 2-(propylamino)acetate 40693-96-7 C7H15NO2
DL-PHENYL(ALANINE-3-13C) DL-PHENYL(ALANINE-3-13C) 286425-42-1 C9H11NO2
TRANS-CINNAMOYL-PHE-OH TRANS-CINNAMOYL-PHE-OH 4950-65-6 C18H17NO3
2-(2-(2-Aminoethoxy)ethoxy)acetic acid hydrochloride 2-(2-(2-Aminoethoxy)ethoxy)acetic acid hydrochloride 134979-01-4 C6H14ClNO4
BOC-ILE-GLY-OH BOC-ILE-GLY-OH 16257-05-9 C13H24N2O5
N-(2-Hydroxyethyl)glycine N-(2-Hydroxyethyl)glycine 5835-28-9 C4H9NO3
(S)-N-Fmoc-2-(3'-butenyl)glycine (S)-N-Fmoc-2-(3'-butenyl)glycine 851909-08-5 C21H21NO4
(R)-N-Fmoc-2-(7'-octenyl)glycine (R)-N-Fmoc-2-(7'-octenyl)glycine 1191429-20-5 C25H29NO4
N-Boc-2-propargyl-glycine N-Boc-2-propargyl-glycine 61172-66-5 C10H15NO4
2-Methoxy-D-Phenylalanine 2-Methoxy-D-Phenylalanine 170642-31-6 C10H13NO3
Cbz-2-Methoxy-D-Phenylalanine Cbz-2-Methoxy-D-Phenylalanine 1270296-34-8 C18H19NO5
Piperazine, 1,4-diacetyl- (6CI,8CI,9CI) Piperazine, 1,4-diacetyl- (6CI,8CI,9CI) 18940-57-3 C8H14N2O2
L-Phenylalanine, 3,4,5-trichloro- L-Phenylalanine, 3,4,5-trichloro- 873429-67-5 C9H8Cl3NO2
N-Acetylcysteine amide N-Acetylcysteine amide 38520-57-9 C5H10N2O2S
DL-2,3-Dimethylphenylalanine DL-2,3-Dimethylphenylalanine 103855-82-9 C11H15NO2
H-GLY-GLY-GLY-OET HCL H-GLY-GLY-GLY-OET HCL 16194-06-2 C8H16ClN3O4
(R)-N-FMoc-2-(2'-propynyl)alanine (R)-N-FMoc-2-(2'-propynyl)alanine 1198791-65-9 C21H19NO4
N-Boc-L-isoleucine heMihydrate N-Boc-L-isoleucine heMihydrate 204138-23-8 C22H44N2O9
FMOC-PHE-PHE-OH FMOC-PHE-PHE-OH 84889-09-8 C33H30N2O5
AC-ILE-NH2 AC-ILE-NH2 56711-06-9 C8H16N2O2
L-PHENYLALANINE-3,3-D2 L-PHENYLALANINE-3,3-D2 221346-31-2 C9H11NO2
N-Fmoc-(S)-2-pentylglycine N-Fmoc-(S)-2-pentylglycine 1197020-22-6 C22H25NO4
PENTAGLYCINE PENTAGLYCINE 7093-67-6 C10H17N5O6
Boc-4-trifluoromethyl-L-homophenylalanine Boc-4-trifluoromethyl-L-homophenylalanine 1260592-66-2 C16H20F3NO4
Fmoc-Ala-Pro-OH Fmoc-Ala-Pro-OH 186023-44-9 C23H24N2O5
N-ALPHA-BENZYLOXYCARBONYL-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE CYCLOHEXYLAMINE N-ALPHA-BENZYLOXYCARBONYL-N'-2,2,4,6,7-PENTAMETHYLDIHYDROBENZOFURAN-5-SULFONYL-L-ARGININE CYCLOHEXYLAMINE 200190-89-2 C33H49N5O7S
2-Methyl-D-homophenylalanine 2-Methyl-D-homophenylalanine 1260614-75-2 C11H15NO2
Boc-2,5-difluoro-D-homophenylalanine Boc-2,5-difluoro-D-homophenylalanine 1260606-61-8 C15H19F2NO4
L-PHENYLALANINE (3-13C) L-PHENYLALANINE (3-13C) 136056-02-5 C9H11NO2
BOC-D-PRA-OH DCHA BOC-D-PRA-OH DCHA 63039-47-4 C22H38N2O4
Alanine-Valine Aminotransferase (Crude Enzyme) Alanine-Valine Aminotransferase (Crude Enzyme)
2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-tritylimidazol-4-yl)propanoyl]amino]acetic acid 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(1-tritylimidazol-4-yl)propanoyl]amino]acetic acid 1428125-85-2 C32H34N4O5
(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-(naphthalen-2-yl)propanoic acid (2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}(methyl)amino)-3-(naphthalen-2-yl)propanoic acid 179385-30-9 C29H25NO4
(R)-BOC-3-METHOXY-BETA-PHE-OH (R)-BOC-3-METHOXY-BETA-PHE-OH 500788-86-3 C15H21NO5
Glycine, N-(2,3-difluorobenzoyl)- Glycine, N-(2,3-difluorobenzoyl)- 1072833-89-6 C9H7F2NO3
Glycine, N-(3,5-difluorobenzoyl)- Glycine, N-(3,5-difluorobenzoyl)- 923691-92-3 C9H7F2NO3
L-Canavanine L-Canavanine 543-38-4 C5H12N4O3
N-CHLOROACETYLGLYCINE N-CHLOROACETYLGLYCINE 6319-96-6 C4H6ClNO3
Borodimethylglycine Borodimethylglycine 77356-05-9 C3H10BNO2
TERT-BUTYL TRANS-4-FORMYLCYCLOHEXYLCARBAMATE TERT-BUTYL TRANS-4-FORMYLCYCLOHEXYLCARBAMATE 181308-57-6 C12H21NO3
3-NITRO-DL-PHENYLALANINE 3-NITRO-DL-PHENYLALANINE 22888-56-8 C9H10N2O4
(RS)-MCPG (RS)-MCPG 146669-29-6 C10H11NO4
Glycine, N-(cyclohexylcarbonyl)-, 2-oxo-1,2-diphenylethyl ester Glycine, N-(cyclohexylcarbonyl)-, 2-oxo-1,2-diphenylethyl ester 1222659-69-9 C23H25NO4
Aluminum zirconium chloride hydroxide Aluminum zirconium chloride hydroxide 57158-29-9 Al2Cl7H7O7Zr2
Palmitoyl Pentapeptide-3 Palmitoyl Pentapeptide-3
2,3-Dichloro-D-Phenylalanine 2,3-Dichloro-D-Phenylalanine 1241677-43-9 C9H9Cl2NO2
4-Phosphonomethyl-L-Phenylalanine 4-Phosphonomethyl-L-Phenylalanine 142434-81-9 C10H14NO5P
Cbz-4-Iodo-L-Phenylalanine Cbz-4-Iodo-L-Phenylalanine 220400-04-4 C17H16INO4
D-4-Iodophenylglycine D-4-Iodophenylglycine 25673-26-1 C8H8INO2
INDOLE-3-ACETYL GLYCINE INDOLE-3-ACETYL GLYCINE 13113-08-1 C12H12N2O3
D(-)4-Hydroxy-Alpa-Phenyl glycine methyl ester HCI D(-)4-Hydroxy-Alpa-Phenyl glycine methyl ester HCI
hexahydrohippurate hexahydrohippurate 32377-88-1 C9H15NO3
(R)-2-Amino-3-(perfluorophenyl)propanoic acid (R)-2-Amino-3-(perfluorophenyl)propanoic acid 40332-58-9 C9H6F5NO2
(R)-N-FMOC-alpha-Methyl-2-fluorophenylalanine, 98% ee, 98% (R)-N-FMOC-alpha-Methyl-2-fluorophenylalanine, 98% ee, 98% 193086-74-7 C25H22FNO4
Z-LEU-GLY-OME Z-LEU-GLY-OME 5084-98-0 C17H24N2O5
AC-PRO-LEU-GLY-OH AC-PRO-LEU-GLY-OH 89626-38-0 C15H25N3O5
BOC-PHE(4-NHAC)-OH BOC-PHE(4-NHAC)-OH 114117-42-9 C16H22N2O5
FMoc-α-Me-Lys(Boc)-OH FMoc-α-Me-Lys(Boc)-OH 1202003-49-3 C27H34N2O6
α-Me-Gly(Butenyl)-OH α-Me-Gly(Butenyl)-OH 1011309-60-6 C7H13NO2
DL-2-FLUORO-3-ALANINE DL-2-FLUORO-3-ALANINE 3821-81-6 C3H6FNO2
(S)-a-Amino-4-(trifluoromethyl)benzenebutanoic acid (S)-a-Amino-4-(trifluoromethyl)benzenebutanoic acid 1260607-82-6 C11H12F3NO2
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