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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
PHT-ILE-OH PHT-ILE-OH 29588-88-3 C14H15NO4
H-GLY-OME.HCL H-GLY-OME.HCL 883886-67-7 C3H8ClNO2
BOC-L-2,4-DIMETHYLPHE BOC-L-2,4-DIMETHYLPHE 849440-31-9 C16H23NO4
ALPHA-METHYL-D-4-FLUOROPHE ALPHA-METHYL-D-4-FLUOROPHE 422568-68-1 C10H12FNO2
H-GLY-ONP HCL H-GLY-ONP HCL 16336-29-1 C8H9ClN2O4
Boc-4-pinicalborane-L-phenylalanine Boc-4-pinicalborane-L-phenylalanine 216439-76-8 C20H30BNO6
N-[(2S)-2-[[(Methylsulfonyl)oxy]methyl]-1-oxo-3-phenylpropyl]-glycine ethyl ester N-[(2S)-2-[[(Methylsulfonyl)oxy]methyl]-1-oxo-3-phenylpropyl]-glycine ethyl ester 1314751-85-3 C15H21NO6S
AMINO(3-BROMOPHENYL)ACETIC ACID AMINO(3-BROMOPHENYL)ACETIC ACID 150174-93-9 C8H8BrNO2
(R)-Ethyl 2-aMino-3-(4-chlorophenyl)propanoate hydrochloride (R)-Ethyl 2-aMino-3-(4-chlorophenyl)propanoate hydrochloride 51366-21-3 C11H15Cl2NO2
H-DL-TYR(ME)-OH H-DL-TYR(ME)-OH 7635-29-2 C10H13NO3
mitochondrial mitochondrial 9028-80-2
L-2-TRIFLUOROMETHYLPHENYLALANINE L-2-TRIFLUOROMETHYLPHENYLALANINE 3832-73-3 C10H10F3NO2
3-TRIFLUOROMETHYL-L-PHENYLALANINE 3-TRIFLUOROMETHYL-L-PHENYLALANINE 14464-68-7 C10H10F3NO2
L-3-NITROPHENYLALANINE L-3-NITROPHENYLALANINE 19883-74-0 C9H10N2O4
Z-DL-PHE(4-CL)-OH Z-DL-PHE(4-CL)-OH 55478-54-1 C17H16ClNO4
Ghk-Cu Ghk-Cu
Betulinic acid gly deriv. Betulinic acid gly deriv. 174740-40-0 C32H51NO4
INDEX NAME NOT YET ASSIGNED INDEX NAME NOT YET ASSIGNED 2278366-87-1 C24H19BrFNO4
N-Acetyl--alanine N-Hydroxysuccinimide Ester N-Acetyl--alanine N-Hydroxysuccinimide Ester 154194-69-1 C9H12N2O5
Fmoc-Gly-Ser[PSI(Me,Me)Pro]-OH Fmoc-Gly-Ser[PSI(Me,Me)Pro]-OH 1095952-22-9 C23H24N2O6
FMoc-D-3-(Methylseleno)-L-alanine FMoc-D-3-(Methylseleno)-L-alanine C19H19NO4Se
FMoc-N-Me-D-Met-OH FMoc-N-Me-D-Met-OH 1932384-22-9 C21H23NO4S
(2S)-2-AMINO-5-HEXENOIC ACID (2S)-2-AMINO-5-HEXENOIC ACID 90989-12-1 C6H11NO2
α-Me-Phe(3-F)-OH α-Me-Phe(3-F)-OH 130855-56-0 C10H12FNO2
4-PHOSPHONOMETHYL-D-PHENYLALANINE 4-PHOSPHONOMETHYL-D-PHENYLALANINE 120667-17-6 C10H14NO5P
Z-PHE-OBZL Z-PHE-OBZL 60379-01-3 C24H23NO4
Fmoc-L-HomoArg(Pbf)-OH Fmoc-L-HomoArg(Pbf)-OH 1159680-21-3 C35H42N4O7S
(S)-2-AMINO-3-(2,4,6-TRIMETHYL-PHENYL)-PROPIONIC ACID (S)-2-AMINO-3-(2,4,6-TRIMETHYL-PHENYL)-PROPIONIC ACID 146277-47-6 C12H17NO2
4-Carboxymethylphenylalanine  hydrochloride 4-Carboxymethylphenylalanine hydrochloride 1803572-24-8 C11H14ClNO4
Z-PHE-PHE-PHE-OH Z-PHE-PHE-PHE-OH 57092-52-1 C35H35N3O6
HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE 19179-12-5 C7H10N2O2
3-amino-4,4-dimethylpentanoic acid hydrochloride 3-amino-4,4-dimethylpentanoic acid hydrochloride 1335041-90-1 C7H16ClNO2
3-aminohex-5-enoic acid hydrochloride 3-aminohex-5-enoic acid hydrochloride 1335042-10-8 C6H12ClNO2
N-DODECYL-N,N-DIMETHYLGLYCINE N-DODECYL-N,N-DIMETHYLGLYCINE 66455-29-6 C16H33NO2
L-Glutamic acid dibenzyl ester tosylate L-Glutamic acid dibenzyl ester tosylate 2791-84-6 C26H29NO7S
Alanine-Valine transaminase (Crude Enzyme) Alanine-Valine transaminase (Crude Enzyme)
DL-HOMOPHENYLALANINE METHYL ESTER HYDROCHLORIDE DL-HOMOPHENYLALANINE METHYL ESTER HYDROCHLORIDE 85808-33-9 C11H16ClNO2
Phosphatidylserine synthase 1 Phosphatidylserine synthase 1
N-Fmoc-(R)-3-trifluoromethyl-homophenylalanine N-Fmoc-(R)-3-trifluoromethyl-homophenylalanine 1260609-38-8 C26H22F3NO4
Z-LEU-PHE-OH Z-LEU-PHE-OH 6401-63-4 C23H28N2O5
TYR-PHE-PHE AMIDE ACETATE SALT TYR-PHE-PHE AMIDE ACETATE SALT 108322-09-4 C27H29N3O5.C2H4O2
DL-ALA-DL-LEU-GLY DL-ALA-DL-LEU-GLY 82267-71-8 C11H21N3O4
N-OLEOYLGLYCINE N-OLEOYLGLYCINE 2601-90-3 C20H37NO3
(S)-11-Benzyl-1-(9H-fluoren-9-yl)-3,6,9,12,15-pentaoxo-2,18-dioxa-4,7,10,13,16-pentaazaicosan-20-oic acid (S)-11-Benzyl-1-(9H-fluoren-9-yl)-3,6,9,12,15-pentaoxo-2,18-dioxa-4,7,10,13,16-pentaazaicosan-20-oic acid 2264011-98-3 C33H35N5O9
DL-4-Iodophenylglycine DL-4-Iodophenylglycine 13370-63-3 C8H8INO2
Fmoc-2,3-Dichloro-L-Phenylalanine Fmoc-2,3-Dichloro-L-Phenylalanine 1260615-87-9 C24H19Cl2NO4
(PYRIDINE-3-CARBONYL)-AMINO-ACETIC ACID ETHYL ESTER (PYRIDINE-3-CARBONYL)-AMINO-ACETIC ACID ETHYL ESTER 54466-74-9 C10H12N2O3
H-DL-PHE-NH2 HCL H-DL-PHE-NH2 HCL 108321-83-1 C9H13ClN2O
GHK-Cu, GHK COPPER GHK-Cu, GHK COPPER
1-STERAOYL-2-LINOLEOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE (MONOSODIUM SALT) 1-STERAOYL-2-LINOLEOYL-SN-GLYCERO-3-PHOSPHO-L-SERINE (MONOSODIUM SALT) 322647-11-0 C42H77NO10P.Na
FMOC-L-3-NITROPHENYLALANINE FMOC-L-3-NITROPHENYLALANINE 206060-42-6 C24H20N2O6
(S)-N-Fmoc-2-(7'-octenyl)glycine (S)-N-Fmoc-2-(7'-octenyl)glycine 1262886-64-5 C25H29NO4
AC-PHE-NHME AC-PHE-NHME 17186-60-6 C12H16N2O2
α-Me-Phe(2-Br)-OH·H<sub>2<sub>O α-Me-Phe(2-Br)-OH·H2O 1212180-27-2 C10H12BrNO2
Boc-3,5-difluoro-D-homophenylalanine Boc-3,5-difluoro-D-homophenylalanine 1260606-36-7 C15H19F2NO4
trans-4-Hydroxy-D-proline trans-4-Hydroxy-D-proline 3398-22-9 C5H9NO3
Z-VAL-GLY-OH Z-VAL-GLY-OH 2790-84-3 C15H20N2O5
1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT 1,2-DISTEAROYL-SN-GLYCERO-3-PHOSPHO-L-SERINE SODIUM SALT 321595-13-5 C42H81NNaO10P
Z-PHE-ILE-OH Z-PHE-ILE-OH 13123-01-8 C23H28N2O5
Fmoc-N-Me-Lys(Boc)-OH Fmoc-N-Me-Lys(Boc)-OH 197632-76-1 C27H34N2O6
L-2-NITROPHENYLALANINE L-2-NITROPHENYLALANINE 19883-75-1 C9H10N2O4
N-O-NITROPHENYLSULFENYL-L-ISOLEUCINE*DCH A N-O-NITROPHENYLSULFENYL-L-ISOLEUCINE*DCH A 10382-52-2 C48H76N6O8S2
N-[1-Oxo-2-(phenylmethyl)-2-propenyl]glycine Ethyl Ester N-[1-Oxo-2-(phenylmethyl)-2-propenyl]glycine Ethyl Ester 660848-81-7 C14H17NO3
Fmoc-2,4-dichloro-D-homophenylalanine Fmoc-2,4-dichloro-D-homophenylalanine 1260613-97-5 C25H21Cl2NO4
FMOC-D-4-TERT-BUTYL-PHE FMOC-D-4-TERT-BUTYL-PHE 252049-14-2 C28H29NO4
AC-P-BROMO-DL-PHE-OH AC-P-BROMO-DL-PHE-OH 273730-59-9 C11H12BrNO3
4,4,4-TRIFLUORO-ALPHA-HOMOALANINE METHYL ESTER HYDROCHLORIDE 4,4,4-TRIFLUORO-ALPHA-HOMOALANINE METHYL ESTER HYDROCHLORIDE 1007583-54-1 C5H9ClF3NO2
((S)-4-cyclohexyl-2-(2-morpholinoacetamido)butanoyl)-L-leucyl-L-phenylalanine ((S)-4-cyclohexyl-2-(2-morpholinoacetamido)butanoyl)-L-leucyl-L-phenylalanine
(R)- 2-(3'-butenyl) alanine (R)- 2-(3'-butenyl) alanine 1932326-29-8 C7H13NO2
2-FLUORO-BETA-ALANINE HYDROCHLORIDE 2-FLUORO-BETA-ALANINE HYDROCHLORIDE 867-84-5 C3H7ClFNO2
(R)-3-AMINOBUTYRIC ACID (R)-3-AMINOBUTYRIC ACID 3775-73-3 C4H9NO2
Fmoc-Ser(tBu)-Gly-OH Fmoc-Ser(tBu)-Gly-OH 81672-17-5 C24H28N2O6
4-amino- L-Phenylalanine, dihydrochloride 4-amino- L-Phenylalanine, dihydrochloride 139879-21-3 C9H13ClN2O2
H-PRO-LEU-GLY-GLY-OH H-PRO-LEU-GLY-GLY-OH 75188-89-5 C15H26N4O5
2-Fluoro-D-homophenylalanine 2-Fluoro-D-homophenylalanine 1260606-28-7 C10H12FNO2
Boc-3,4-difluoro-D-homophenylalanine Boc-3,4-difluoro-D-homophenylalanine 1260588-78-0 C15H19F2NO4
FMOC-N-(N-BETA-BOC-AMINOETHYL)-GLY-OH FMOC-N-(N-BETA-BOC-AMINOETHYL)-GLY-OH 141743-15-9 C24H28N2O6
Phenylalanine Agar Phenylalanine Agar
(S)-2-Amino-4-(3-trifluoromethylphenyl)butanoic acid (S)-2-Amino-4-(3-trifluoromethylphenyl)butanoic acid 1260614-67-2 C11H12F3NO2
Fmoc-3,4-dichloro-D-homophenylalanine Fmoc-3,4-dichloro-D-homophenylalanine 1260618-71-0 C25H21Cl2NO4
Fmoc-N-Me-D-Phe(2-F)-OH Fmoc-N-Me-D-Phe(2-F)-OH
FMOC-ALA-GLY-OH FMOC-ALA-GLY-OH 116747-54-7 C20H20N2O5
L-4-CYANOPHENYLALANINE L-4-CYANOPHENYLALANINE 104531-20-6 C10H11ClN2O2
Z-ALA-PHE-OH Z-ALA-PHE-OH 2768-53-8 C20H22N2O5
Fomc-Gly-Gly-Phe-Gly-OH Fomc-Gly-Gly-Phe-Gly-OH 1817857-75-2 C30H30N4O7
2,4-dinitro-3-phenyl-L-alanine 2,4-dinitro-3-phenyl-L-alanine 49607-21-8 C9H9N3O6
trisodium [N,N-bis[2-[bis(carboxylatomethyl)amino]ethyl]glycinato(5-)]zincate(3-) trisodium [N,N-bis[2-[bis(carboxylatomethyl)amino]ethyl]glycinato(5-)]zincate(3-) 11082-38-5 C14H18N3O10Zn.3Na
3-Amino-DL-Phenylalanine 3-Amino-DL-Phenylalanine 28101-74-8 C9H12N2O2
Glycine, N,N'-[1-(4,5-dimethoxy-2-nitrophenyl)-1,2-ethanediyl]bis[N-(carboxymethyl)-, tetrasodium salt (9CI) Glycine, N,N'-[1-(4,5-dimethoxy-2-nitrophenyl)-1,2-ethanediyl]bis[N-(carboxymethyl)-, tetrasodium salt (9CI) 291517-40-3 C18H24N3NaO12
2-IODO-DL-PHENYLALANINE 2-IODO-DL-PHENYLALANINE 1986-86-3 C9H10INO2
NGR Asn-Gly-Arg NGR Asn-Gly-Arg
Z-ALA-PHE-OME Z-ALA-PHE-OME 3235-14-1 C21H24N2O5
Z-D-ALA-GLY-OH Z-D-ALA-GLY-OH 34286-66-3 C13H16N2O5
Z-GLY-GLY-GLY-GLY-OH Z-GLY-GLY-GLY-GLY-OH 7770-50-5 C16H20N4O7
FOR-ILE-OH FOR-ILE-OH C7H13NO3
DL-2,6-DIFLUOROPHENYLALANINE DL-2,6-DIFLUOROPHENYLALANINE 33787-05-2 C9H9F2NO2
H-LEU-GLY-BETANA H-LEU-GLY-BETANA 100930-00-5 C18H23N3O2
POLY(LYS, PHE) HYDROBROMIDE POLY(LYS, PHE) HYDROBROMIDE 26700-39-0 C15H25N3O4
Ethyl (S)-2-aMino-3-(4-broMophenyl) propanoate hydrochloride Ethyl (S)-2-aMino-3-(4-broMophenyl) propanoate hydrochloride 232276-00-5 C11H15BrClNO2
(S)-1-Amino-2-hydroxymethylindoline (S)-1-Amino-2-hydroxymethylindoline 27719-98-8 C9H12N2O
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