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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-D-ALA-PNA HCL H-D-ALA-PNA HCL C9H12ClN3O3
Boc-L-3-Bromophenylalanine Boc-L-3-Bromophenylalanine 82278-95-3 C14H18BrNO4
FOR-MET-LEU-PHE-PHE-OH FOR-MET-LEU-PHE-PHE-OH 80180-63-8 C30H40N4O6S
FMOC-LEU-ONP FMOC-LEU-ONP 71989-25-8 C27H26N2O6
3-Thiophenecarboxylicacid,2-amino-(9CI) 3-Thiophenecarboxylicacid,2-amino-(9CI) 56387-08-7 C5H5NO2S
1H-Benzimidazole-5-carboxylicacid,2-amino-,methylester(9CI) 1H-Benzimidazole-5-carboxylicacid,2-amino-,methylester(9CI) 106429-38-3 C9H9N3O2
Benzoic acid, 3-acetyl-4-amino-, methyl ester (9CI) Benzoic acid, 3-acetyl-4-amino-, methyl ester (9CI) 111714-47-7 C10H11NO3
2-NITRO-DL-PHENYLALANINE 2-NITRO-DL-PHENYLALANINE 35378-63-3 C9H10N2O4
H-DL-GLA-OH H-DL-GLA-OH 56271-99-9 C6H9NO6
N-tert-Butyloxycarbonyl-S-(4-methylbenzyl)-D-penicillamine dicyclohexylamine N-tert-Butyloxycarbonyl-S-(4-methylbenzyl)-D-penicillamine dicyclohexylamine 198474-61-2 C30H50N2O4S
BENZYL 5-AMINO-4-[(TERT-BUTOXYCARBONYL)AMINO]-5-OXOPENTANOATE BENZYL 5-AMINO-4-[(TERT-BUTOXYCARBONYL)AMINO]-5-OXOPENTANOATE 292870-04-3 C17H24N2O5
DNP-L-ASPARTIC ACID DNP-L-ASPARTIC ACID 7683-81-0 C10H9N3O8
N-[ALPHA-[2-(PIPERIDINOACETAMIDO)PHENYL]BENZYLIDENE]GLYCINATO]NICKEL N-[ALPHA-[2-(PIPERIDINOACETAMIDO)PHENYL]BENZYLIDENE]GLYCINATO]NICKEL 847654-17-5 C22H23N3NiO3
FMOC-GAMMA-ABU-OH FMOC-GAMMA-ABU-OH 116821-47-7 C19H19NO4
POLY-L-PHENYLALANINE POLY-L-PHENYLALANINE 25191-15-5 (C9H11NO2)x
5-HYDROXY-L-TRYPTOPHAN HYDRATE 5-HYDROXY-L-TRYPTOPHAN HYDRATE 145224-90-4 C11H14N2O4
FMOC-BETA-CYCLOBUTYL-D-ALA-OH FMOC-BETA-CYCLOBUTYL-D-ALA-OH 478183-63-0 C22H23NO4
ETHYL 2-AMINOINDOLE-3-CARBOXYLATE ETHYL 2-AMINOINDOLE-3-CARBOXYLATE 6433-72-3 C11H12N2O2
H-ALA-OBZL HCL H-ALA-OBZL HCL 557-83-5 CBF3N.H
CYS-GLY CYS-GLY 19246-18-5 C5H10N2O3S
BOC-(R)-ALPHA-BENZYL-PROLINE BOC-(R)-ALPHA-BENZYL-PROLINE 706806-60-2 C17H23NO4
L-ISOLEUCINE-15N L-ISOLEUCINE-15N 59935-30-7 C6H13NO2
BOC-N,2-DIMETHYLALANINE BOC-N,2-DIMETHYLALANINE 146000-39-7 C10H19NO4
POLY-(ALPHA,BETA)-DL-ASPARTIC ACID SODIUM SALT POLY-(ALPHA,BETA)-DL-ASPARTIC ACID SODIUM SALT 94525-01-6 C4H5NNa2O4
BOC-D-3,3-DIPHENYLALANINE BOC-D-3,3-DIPHENYLALANINE 117027-46-0 C20H23NO4
3-CHLORO-L-TYROSINE HYDROCHLORIDE 3-CHLORO-L-TYROSINE HYDROCHLORIDE 35608-63-0 C9H11Cl2NO3
AC-DL-PHG-OH AC-DL-PHG-OH 15962-46-6 C10H11NO3
(S)-N-Acetyl-2-naphthylalanine (S)-N-Acetyl-2-naphthylalanine 37439-99-9 C15H15NO3
BOC-ALA-ALA-OME BOC-ALA-ALA-OME 19794-10-6 C12H22N2O5
H-SER(TBU)-OTBU HCL H-SER(TBU)-OTBU HCL 51537-21-4 C11H24ClNO3
H-D-ALA-ONAP(1) HCL H-D-ALA-ONAP(1) HCL 213179-01-2 C13H14ClNO2
S-(4-NITROPHENYL)CYSTEINYLGLYCINE HYDROCHLORIDE S-(4-NITROPHENYL)CYSTEINYLGLYCINE HYDROCHLORIDE 382631-41-6 C11H14ClN3O5S
4-(2-AMINOETHYL)BENZOIC ACID HYDROCHLORIDE 4-(2-AMINOETHYL)BENZOIC ACID HYDROCHLORIDE 60531-36-4 C9H12ClNO2
N,N-DIMETHYL-L-VALINE N,N-DIMETHYL-L-VALINE 2812-32-0 C7H15NO2
4-CIS-FLUORO-L-PROLINAMIDE HYDROCHLORIDE 4-CIS-FLUORO-L-PROLINAMIDE HYDROCHLORIDE 426844-23-7 C5H10ClFN2O
Z-D-NLE-OH Z-D-NLE-OH 15027-14-2 C14H19NO4
DL-7-Azatryptophan hydrate DL-7-Azatryptophan hydrate 7146-37-4 C10H13N3O3
ETHYL 2-[(2-CHLOROACETYL)AMINO]ACETATE ETHYL 2-[(2-CHLOROACETYL)AMINO]ACETATE 41602-50-0 C6H10ClNO3
FMOC-L-LYS(DANSYL)-OH FMOC-L-LYS(DANSYL)-OH 118584-90-0 C33H35N3O6S
BOC-(R)-2-THIENYLGLYCINE BOC-(R)-2-THIENYLGLYCINE 74562-03-1 C11H15NO4S
GLYCINE BETA-NAPHTHYLAMIDE HYDROCHLORIDE GLYCINE BETA-NAPHTHYLAMIDE HYDROCHLORIDE 1208-12-4 C12H13ClN2O
BENZOYL-L-LEUCINE BENZOYL-L-LEUCINE 1466-83-7 C13H17NO3
METHYL (2S,4R)-4-FLUOROPROLINATE METHYL (2S,4R)-4-FLUOROPROLINATE 126111-11-3 C6H10FNO2
N-ME-PHE-OME HCL N-ME-PHE-OME HCL 19460-86-7 C11H16ClNO2
FMOC-(S)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID FMOC-(S)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID C31H27NO4
POTASSIUM L-GLUTAMATE MONOHYDRATE POTASSIUM L-GLUTAMATE MONOHYDRATE C5H10KNO5
Boc-D-Cyclobutylglycine Boc-D-Cyclobutylglycine 155905-78-5 C11H19NO4
S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID S-ACETAMIDOMETHYL-3-MERCAPTOPROPIONIC ACID 52574-08-0 C6H11NO3S
BOC-N-ETHYL GLYCINE BOC-N-ETHYL GLYCINE 149794-10-5 C9H17NO4
FMOC-ARG(Z)2-OH FMOC-ARG(Z)2-OH 207857-35-0 C37H36N4O8
DNP-L-ISOLEUCINE DNP-L-ISOLEUCINE 1655-56-7 C12H15N3O6
N-ACETYL-S-(4-NITROPHENYL)CYSTEINYLGLYCINE N-ACETYL-S-(4-NITROPHENYL)CYSTEINYLGLYCINE 375855-09-7 C13H15N3O6S
H-PHE(4-NH-BOC)-OH H-PHE(4-NH-BOC)-OH 74578-48-6 C14H20N2O4
BOC-BETA-CYANO-ALA-OH BOC-BETA-CYANO-ALA-OH 45159-34-0 C9H14N2O4
H-GLY-TYR-PRO-GLY-GLN-VAL-OH H-GLY-TYR-PRO-GLY-GLN-VAL-OH 225779-44-2 C28H41N7O9
FMOC-HIS(3-BOM)-OH FMOC-HIS(3-BOM)-OH 84891-19-0 C29H27N3O5
H-D-CIT-OH H-D-CIT-OH 13594-51-9 C6H13N3O3
CHLOROAC-ILE-OH CHLOROAC-ILE-OH 67253-30-9 C8H14ClNO3
S-Adenosyl-L-methionine tosylate S-Adenosyl-L-methionine tosylate 71914-80-2 C15H23N6O5S.C7H7O3S
L-4-PYRIDYLALANINE L-4-PYRIDYLALANINE 178933-04-5 C8H11ClN2O2
N-(9-FLUORENYLMETHOXYCARBONYL)-L-ALANIN& N-(9-FLUORENYLMETHOXYCARBONYL)-L-ALANIN& 117398-49-9 C18H17NO4
DL-TYROSINE METHYL ESTER HCL DL-TYROSINE METHYL ESTER HCL 68697-61-0 C10H14ClNO3
N-Tetradecanoyl-4-hydroxy-L-proline N-Tetradecanoyl-4-hydroxy-L-proline 848390-99-8 C19H35NO4
Sodium N-hexadecanoyl-L-alaninate Sodium N-hexadecanoyl-L-alaninate 67395-94-2 C19H36NNaO3
Sodium N-dodecanoyl-L-valinate Sodium N-dodecanoyl-L-valinate 37869-33-3 C17H32NNaO3
PHE-ALA-ALA-P-NITRO-PHE-PHE-VAL-LEU 4-PYRIDYLMETHYL ESTER PHE-ALA-ALA-P-NITRO-PHE-PHE-VAL-LEU 4-PYRIDYLMETHYL ESTER 115389-04-3 C50H63N9O10
L-(-)-Histidinol dihydrochloride L-(-)-Histidinol dihydrochloride 1596-64-1 C6H13Cl2N3O
BOC-HOARG-OH BOC-HOARG-OH 128719-65-3 C12H24N4O4
GLY-PRO 4-METHOXY-BETA-NAPHTHYLAMIDE GLY-PRO 4-METHOXY-BETA-NAPHTHYLAMIDE 42761-76-2 C18H21N3O3
BOC-(S)-2-THIENYLGLYCINE BOC-(S)-2-THIENYLGLYCINE 40512-56-9 C11H15NO4S
N-ALPHA-ACETYL-L-ORNITHINE N-ALPHA-ACETYL-L-ORNITHINE 6205-08-9 C7H14N2O3
6-CHLORO-D-TRYPTOPHAN 6-CHLORO-D-TRYPTOPHAN 56632-86-1 C11H11ClN2O2
(R)-3-AMINO-3-(3-BROMO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(3-BROMO-PHENYL)-PROPIONIC ACID C9H10BrNO2
Z-N-ME-GLU(OTBU)-OH Z-N-ME-GLU(OTBU)-OH 42417-71-0 C18H25NO6
BOC-HIS(1-ME)-OH BOC-HIS(1-ME)-OH 61070-20-0 C12H19N3O4
5-AMINO-1H-BENZOIMIDAZOLE-2-CARBOXYLIC ACID METHYL ESTER 5-AMINO-1H-BENZOIMIDAZOLE-2-CARBOXYLIC ACID METHYL ESTER 292070-01-0 C9H9N3O2
H-D-GLN(TRT)-OH H-D-GLN(TRT)-OH 200625-76-9 C24H24N2O3
Methyl (S)-3-acetamido-3-(4-chlorophenyl)propanoate Methyl (S)-3-acetamido-3-(4-chlorophenyl)propanoate 434957-75-2 C12H14ClNO3
Methyl (R)-3-acetamido-3-phenylpropanoate Methyl (R)-3-acetamido-3-phenylpropanoate 67654-57-3 C12H15NO3
D-Aspartic Acid diethyl ester hydrochloride D-Aspartic Acid diethyl ester hydrochloride 112018-26-5 C8H16ClNO4
fmoc-D-2-cyanophenylalanine fmoc-D-2-cyanophenylalanine 401620-74-4 C25H20N2O4
POLY-GAMMA-BENZYL L-GLUTAMATE POLY-GAMMA-BENZYL L-GLUTAMATE 25014-27-1 C12H15NO4
(1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid (1S,2S)-(-)-2-Amino-1-cyclopentanecarboxylic acid 64191-13-5 C6H11NO2
FMOC-D-DAB(FMOC)-OH FMOC-D-DAB(FMOC)-OH 114360-56-4 C24H28N2O6
(1R,2S)-2-Aminocyclopentanecarboxylic acid (1R,2S)-2-Aminocyclopentanecarboxylic acid 122672-46-2 C6H11NO2
BOC-BETA-ALA-ONP BOC-BETA-ALA-ONP 17547-09-0 C14H18N2O6
H-PRO-LEU-GLY-NHOH HCL H-PRO-LEU-GLY-NHOH HCL 120928-08-7 C13H25ClN4O4
FMOC-TYR(MALONYL-DI-OTBU)-OH FMOC-TYR(MALONYL-DI-OTBU)-OH 168135-77-1 C35H39NO9
FMOC-D-ASP-NH2 FMOC-D-ASP-NH2 200335-41-7 C19H18N2O5
FMOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID 511272-51-8 C24H20FNO4
4-Pyridinecarboxylicacid,2-(acetylamino)-,methylester(9CI) 4-Pyridinecarboxylicacid,2-(acetylamino)-,methylester(9CI) 98953-21-0 C9H10N2O3
5-Isoxazolealanine,3-methyl-(6CI) 5-Isoxazolealanine,3-methyl-(6CI) 100959-34-0 C7H10N2O3
carbobenzoxyhomoserine carbobenzoxyhomoserine 41088-85-1 C12H15NO5
H-His(Trt)-OMe · HCl H-His(Trt)-OMe · HCl 32946-56-8 C26H25N3O2.ClH
Fmoc-D-Threoninol Fmoc-D-Threoninol 252049-02-8 C19H21NO4
FMOC-LYS(PALMITOYL)-OH FMOC-LYS(PALMITOYL)-OH 201004-46-8 C37H54N2O5
N-(TRIPHENYLMETHYL)-DL-SERINE METHYL ESTER N-(TRIPHENYLMETHYL)-DL-SERINE METHYL ESTER 13515-76-9 C23H23NO3
3-(1-NAPHTHYL)-L-ALANINE HYDROCHLORIDE 3-(1-NAPHTHYL)-L-ALANINE HYDROCHLORIDE 122745-10-2 C13H13NO2.HCl
FMOC-BETA-(2-QUINOLYL)-ALA-OH FMOC-BETA-(2-QUINOLYL)-ALA-OH 214852-56-9 C27H22N2O4
L-PHENYL-D5-ALANINE-2,3,3-D3 L-PHENYL-D5-ALANINE-2,3,3-D3 17942-32-4 C9H3D8NO2
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