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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
L-CANALINE BASE L-CANALINE BASE 496-93-5 C4H10N2O3
5-(CARBOBENZOXYAMINO)VALERIC ACID 5-(CARBOBENZOXYAMINO)VALERIC ACID 23135-50-4 C13H17NO4
GLUTARIC ACID-2-METHYLAMINO-5-NITROMONOANILIDE GLUTARIC ACID-2-METHYLAMINO-5-NITROMONOANILIDE 91644-13-2 C12H15N3O5
Sodium N-palmitoyl-L-serinate Sodium N-palmitoyl-L-serinate 58725-46-5 C19H36NNaO4
N-Myristoyl-L-serine N-Myristoyl-L-serine 21394-57-0 C17H33NO4
3-METHOXY-DL-TYROSINE 3-METHOXY-DL-TYROSINE 4214-13-5 C10H13NO4
BOC-ALPHA-METHYL-D-TYR BOC-ALPHA-METHYL-D-TYR C15H21NO5
BOC-D-PHE(2-I)-OH BOC-D-PHE(2-I)-OH 478183-64-1 C14H18INO4
FMOC-SER(AC)-OH FMOC-SER(AC)-OH 171778-17-9 C20H19NO6
FMOC-[15N]PHE-OH FMOC-[15N]PHE-OH 125700-32-5 C24H21NO4
BOC-D-MEPHE(4-CL)-OH BOC-D-MEPHE(4-CL)-OH 125324-00-7 C15H20ClNO4
GLY-ASP-ASP-ASP-ASP-LYS BETA-NAPHTHYLAMIDE GLY-ASP-ASP-ASP-ASP-LYS BETA-NAPHTHYLAMIDE 70023-02-8 C34H44N8O14
L-BETA-HOMOTHREONINE HCL L-BETA-HOMOTHREONINE HCL 192003-00-2 C5H11NO3
H-THR-OBZL OXALATE (1:1) H-THR-OBZL OXALATE (1:1) 201274-07-9 C13H17NO7
(R)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(2-BROMO-PHENYL)-PROPIONIC ACID C9H10BrNO2
(R)-3-AMINO-4-(2,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(2,4-DICHLOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 331847-13-3 C10H12Cl3NO2
3-[[(1,1-Dimethylethoxy)carbonyl]amino]-L-alanine methyl ester 3-[[(1,1-Dimethylethoxy)carbonyl]amino]-L-alanine methyl ester 77087-60-6 C9H18N2O4
Ethyl 2-(acetylamino)-3-[3,5-diamino-4-(4-methoxyphenoxy)phenyl]propanoate Ethyl 2-(acetylamino)-3-[3,5-diamino-4-(4-methoxyphenoxy)phenyl]propanoate 440667-78-7 C20H25N3O5
(S)-N-BOC-2-AMINO-3-ETHOXY-PROPIONIC ACID (S)-N-BOC-2-AMINO-3-ETHOXY-PROPIONIC ACID 104839-00-1 C10H19NO5
L-Valine hydrochloride L-Valine hydrochloride 17498-50-9 C5H12ClNO2
FMOC-ALA-N-CARBOXYANHYDRIDE FMOC-ALA-N-CARBOXYANHYDRIDE 125814-20-2 C19H15NO5
3-CHLORO-4-FLUORO-DL-PHENYLGLYCINE 3-CHLORO-4-FLUORO-DL-PHENYLGLYCINE 261762-99-6 C8H7ClFNO2
(R)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID CL (R)-3-AMINO-4-(2,4-DICHLORO-PHENYL)-BUTYRIC ACID CL C10H12Cl3NO2
Sodium 1-lauroyl-L-prolinate Sodium 1-lauroyl-L-prolinate 70609-63-1 C17H30NNaO3
N-Dodecanoyl-L-valine N-Dodecanoyl-L-valine 14379-28-3 C17H33NO3
ALPHA-METHYL-DL-HISTIDINE DIHYDROCHLORIDE ALPHA-METHYL-DL-HISTIDINE DIHYDROCHLORIDE 32381-18-3 C7H13Cl2N3O2
(S)-2-(DIBENZYLAMINO)-3-METHYL-1-BUTANOL (S)-2-(DIBENZYLAMINO)-3-METHYL-1-BUTANOL 111060-54-9 C19H25NO
Z-IETD-AFC Z-IETD-AFC 219138-02-0 C37H42F3N5O13
POLY-L-ARGININE HYDROCHLORIDE POLY-L-ARGININE HYDROCHLORIDE 26982-20-7 C6H14N4O2
TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER TRANS-1-BENZOYL-4-HYDROXY-L-PROLINE METHYL ESTER 120806-96-4 C13H15NO4
4-AMINOBUTYLPHOSPHONIC ACID 4-AMINOBUTYLPHOSPHONIC ACID 35622-27-6 C4H12NO3P
BOC-L-TYROSINE ETHYL ESTER BOC-L-TYROSINE ETHYL ESTER 72594-77-5 C16H23NO5
(+)-N-BENZOYLGLUTAMIC ACID (+)-N-BENZOYLGLUTAMIC ACID 58094-18-1 C12H13NO5
Alanosine Alanosine 5854-93-3 C3H7N3O4
Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate Methyl (R)-3-acetamido-3-(4-chlorophenyl)propanoate 810670-03-2 C12H14ClNO3
Ethylenediamine-N,N'-bis((2-hydroxyphenyl)acetic acid) Ethylenediamine-N,N'-bis((2-hydroxyphenyl)acetic acid) 1170-02-1 C18H20N2O6
Boc-L-3-Bromophenylalanine Boc-L-3-Bromophenylalanine 82278-95-3 C14H18BrNO4
S-Butyl-D-cysteine S-Butyl-D-cysteine 4134-56-9 C7H15NO2S
3-(N,N-Diethylamino)-L-alanine 3-(N,N-Diethylamino)-L-alanine 754167-24-3 C7H16N2O2
H-D-ALA-PNA HCL H-D-ALA-PNA HCL C9H12ClN3O3
DL-Glutamine DL-Glutamine 6899-04-3 C5H10N2O3
3-hydroxyglutamic acid 3-hydroxyglutamic acid 533-62-0 C5H9NO5
3-(N,N-Diethanolamino)-L-alanine 3-(N,N-Diethanolamino)-L-alanine 700801-50-9 C7H16N2O4
Boc-L-glutamic acid γ-allyl ester Boc-L-glutamic acid γ-allyl ester 132286-79-4 C13H21NO6
Fmoc-L-allo-isoleucine Fmoc-L-allo-isoleucine 251316-98-0 C21H23NO4
N-BOC-(S)-2-AMINO-1-BUTANOL, 96% N-BOC-(S)-2-AMINO-1-BUTANOL, 96% 150736-72-4 C9H19NO3
3-Imidazolyl-L-alanine 3-Imidazolyl-L-alanine 114717-14-5 C6H9N3O2
3-(N,N-Dimethylamino)-D-alanine 3-(N,N-Dimethylamino)-D-alanine 206559-98-0 C5H12N2O2
BETA-(1,2,4-TRIAZOL-3-YL)-DL-ALANINE BETA-(1,2,4-TRIAZOL-3-YL)-DL-ALANINE 3184-54-1 C5H8N4O2
FMOC-(S)-3-AMINO-3-(4-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID FMOC-(S)-3-AMINO-3-(4-TRIFLUOROMETHYL-PHENYL)-PROPIONIC ACID 507472-21-1 C25H20F3NO4
3-(4-Pyridyl)-DL-alanine 3-(4-Pyridyl)-DL-alanine 1956-21-4 C8H10N2O2
S-Trityl-D-cysteine S-Trityl-D-cysteine 25840-82-8 C22H21NO2S
(S)-3-TERT-BUTYL-BETA-ALANINE
(S)-3-TERT-BUTYL-BETA-ALANINE 367278-48-6 C7H15NO2
3-CHLORO-DL-PHENYLALANINE 3-CHLORO-DL-PHENYLALANINE 1956-15-6 C9H10ClNO2
FMOC-2-AMINOBENZOIC ACID FMOC-2-AMINOBENZOIC ACID 150256-42-1 C22H17NO4
L-VINYLGLYCINE L-VINYLGLYCINE 70982-53-5 C4H7NO2
L-TYROSINOL L-TYROSINOL 5034-68-4 C9H13NO2
Z-ABU-OH Z-ABU-OH 42918-86-5 C12H15NO4
POLY-L-ASPARTIC ACID SODIUM SALT POLY-L-ASPARTIC ACID SODIUM SALT 31871-95-1 (C4H5NO3)n.Na
DIRHODIUM TETRAKIS[N-PHTHALOYL-(S)-TERT-LEUCINATE] BIS(ETHYL ACETATE) ADDUCT DIRHODIUM TETRAKIS[N-PHTHALOYL-(S)-TERT-LEUCINATE] BIS(ETHYL ACETATE) ADDUCT 154090-43-4 C64H72N4O20Rh2
DIRHODIUM TETRAKIS[N-PHTHALOYL-(R)-TERT-LEUCINATE] BIS(ETHYL ACETATE) ADDUCT DIRHODIUM TETRAKIS[N-PHTHALOYL-(R)-TERT-LEUCINATE] BIS(ETHYL ACETATE) ADDUCT 380375-05-3 C64H72N4O20Rh2
N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER N-(METHOXYCARBONYL)-L-TRYPTOPHAN METHYL ESTER 58635-46-4 C14H16N2O4
Z-GLN(XAN)-OH Z-GLN(XAN)-OH 327981-01-1 C26H24N2O6
H-ALA-ONP HCL H-ALA-ONP HCL 17463-53-5 C9H11ClN2O4
Z-TYR(TBU)-OSU Z-TYR(TBU)-OSU 10068-67-4 C25H28N2O7
BOC-VAL-LEU-LYS-AMC ACETATE BOC-VAL-LEU-LYS-AMC ACETATE 73554-84-4 C32H49N5O7
DL-PHENYLALANINE-OBZL P-TOSYLATE DL-PHENYLALANINE-OBZL P-TOSYLATE 119290-61-8 C23H25NO5S
FMOC-6-AMINOHEXANOIC ACID FMOC-6-AMINOHEXANOIC ACID 88574-06-5 C21H23NO4
AMINO-(3,4-DIHYDROXY-PHENYL)-ACETIC ACID AMINO-(3,4-DIHYDROXY-PHENYL)-ACETIC ACID 138-62-5 C8H9NO4
(RS)-3,5-DHPG (RS)-3,5-DHPG 19641-83-9 C8H9NO4
BOC-(R)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID C15H21NO4
BOC-D-PYR-OH BOC-D-PYR-OH 160347-90-0 C10H15NO5
N-(2,4-DINITROPHENYL)-L-METHIONINE DICYCLOHEXYLAMMONIUM SALT N-(2,4-DINITROPHENYL)-L-METHIONINE DICYCLOHEXYLAMMONIUM SALT C23H36N4O6S
N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID N-BOC-(+/-)-2-AMINO-3-HYDROXY-3-METHYLBUTANOIC ACID 105504-72-1 C10H19NO5
(R)-N-BOC-(5-BROMO-2-METHOXYPHENYL)ALANINE (R)-N-BOC-(5-BROMO-2-METHOXYPHENYL)ALANINE 261380-17-0 C15H20BrNO5
AMINOPYRALID AMINOPYRALID 150114-71-9 C6H4Cl2N2O2
FMOC-DAP(Z)-OH FMOC-DAP(Z)-OH 204316-36-9 C26H24N2O6
H-ILE-ILE-GLY-LEU-MET-OH H-ILE-ILE-GLY-LEU-MET-OH 149385-65-9 C25H47N5O6S
FMOC-4-AMINO-D-PHENYLALANINE FMOC-4-AMINO-D-PHENYLALANINE 324017-21-2 C24H22N2O4
BOC-3-CHLORO-L-TYROSINE BOC-3-CHLORO-L-TYROSINE 192315-36-9 C14H18ClNO5
(2S)-2,6-DIAMINO-N-[(1S)-1-METHYL-2-PHENYLETHYL]HEXANAMIDE DIMETHANESULFONATE (2S)-2,6-DIAMINO-N-[(1S)-1-METHYL-2-PHENYLETHYL]HEXANAMIDE DIMETHANESULFONATE 608137-33-3 C16H29N3O4S
D-Proline, 1-glycyl- (9CI) D-Proline, 1-glycyl- (9CI) 71884-56-5 C7H12N2O3
Benzoic acid, 3-acetyl-4-amino-, methyl ester (9CI) Benzoic acid, 3-acetyl-4-amino-, methyl ester (9CI) 111714-47-7 C10H11NO3
Pyrazinecarboxylic acid, 6-amino- (9CI) Pyrazinecarboxylic acid, 6-amino- (9CI) 61442-38-4 C5H5N3O2
3-(Dimethylamino)propanoicacid 3-(Dimethylamino)propanoicacid 6300-04-5 C5H11NO2
N-Boc-1-phenylmethyl-D-histidine N-Boc-1-phenylmethyl-D-histidine 65717-64-8 C18H23N3O4
(R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL
(R)-N-BOC-3-AMINO-3-PHENYL-PROPAN-1-OL 158807-47-7 C14H21NO3
1-N-CBZ-4-HYDROXY-BETA-PROLINE
1-N-CBZ-4-HYDROXY-BETA-PROLINE 886362-64-7 C13H15NO5
H-DL-GLA-OH H-DL-GLA-OH 56271-99-9 C6H9NO6
2-NITRO-DL-PHENYLALANINE 2-NITRO-DL-PHENYLALANINE 35378-63-3 C9H10N2O4
BENZYL 5-AMINO-4-[(TERT-BUTOXYCARBONYL)AMINO]-5-OXOPENTANOATE BENZYL 5-AMINO-4-[(TERT-BUTOXYCARBONYL)AMINO]-5-OXOPENTANOATE 292870-04-3 C17H24N2O5
N-tert-Butyloxycarbonyl-S-(4-methylbenzyl)-D-penicillamine dicyclohexylamine N-tert-Butyloxycarbonyl-S-(4-methylbenzyl)-D-penicillamine dicyclohexylamine 198474-61-2 C30H50N2O4S
1H-Benzimidazole-5-carboxylicacid,2-amino-,methylester(9CI) 1H-Benzimidazole-5-carboxylicacid,2-amino-,methylester(9CI) 106429-38-3 C9H9N3O2
3-Thiophenecarboxylicacid,2-amino-(9CI) 3-Thiophenecarboxylicacid,2-amino-(9CI) 56387-08-7 C5H5NO2S
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
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
5-HYDROXY-L-TRYPTOPHAN HYDRATE 5-HYDROXY-L-TRYPTOPHAN HYDRATE 145224-90-4 C11H14N2O4
POLY-L-PHENYLALANINE POLY-L-PHENYLALANINE 25191-15-5 (C9H11NO2)x
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