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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
N-BSMOC-L-METHIONINE N-BSMOC-L-METHIONINE 197245-29-7 C15H17NO6S2
FMOC-ABU-OH FMOC-ABU-OH 135112-27-5 C19H19NO4
BOC-PHE-GLY-OME BOC-PHE-GLY-OME 7625-57-2 C17H24N2O5
Z-GLY-GLY-SER-OH Z-GLY-GLY-SER-OH 98352-76-2 C15H19N3O7
(2S)-1,2-PYRROLIDINEDICARBOXYLIC ACID-1-ETHYL-2-METHYL ESTER (2S)-1,2-PYRROLIDINEDICARBOXYLIC ACID-1-ETHYL-2-METHYL ESTER 93423-88-2 C9H15NO4
DL-N-BENZOYL-2-METHYLSERINE DL-N-BENZOYL-2-METHYLSERINE 7508-82-9 C11H13NO4
D-Thyroxine D-Thyroxine 51-49-0 C15H11I4NO4
(S)-N-(5-AMINO-1-CARBOXYPENTYL)IMINODIACETIC ACID HYDRATE (S)-N-(5-AMINO-1-CARBOXYPENTYL)IMINODIACETIC ACID HYDRATE 113231-05-3 C10H18N2O6
(4S)-4-hydroxy-L-proline hydrochloride (4S)-4-hydroxy-L-proline hydrochloride 441067-49-8 C5H10ClNO3
METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE METHYL 2-(S)-[N-CARBOBENZYLOXY]AMINO-3-AMINOPROPIONATE, HYDROCHLORIDE 35761-27-4 C12H17ClN2O4
FMOC-D-PEN(TRT)-OH FMOC-D-PEN(TRT)-OH 201532-01-6 C39H35NO4S
N-Boc-cis-4-Fluoro-L-proline methyl ester N-Boc-cis-4-Fluoro-L-proline methyl ester 203866-16-4 C11H18FNO4
N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride 211914-50-0 C27H30ClN7O3
H-ALA-ALA-OME HCL H-ALA-ALA-OME HCL 41036-19-5 C7H15ClN2O3
(R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL (R)-(1,2,3,4-TETRAHYDROISOQUINOLIN-3-YL)-METHANOL 62855-02-1 C10H13NO
ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE ERYTHRO-N-BOC-O-BENZYL-L-TYROSINE EPOXIDE 162536-84-7 C22H27NO4
GLY-DL-LEU-DL-ALA GLY-DL-LEU-DL-ALA 78681-93-3 C11H21N3O4
BOC-(R)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(4-HYDROXY-PHENYL)-PROPIONIC ACID 329013-12-9 C14H19NO5
(S)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID HCL (S)-3-AMINO-4,4-DIPHENYL-BUTYRIC ACID HCL 544455-95-0 C16H17NO2
BOC-P-FLUORO-DL-PHE-OH BOC-P-FLUORO-DL-PHE-OH 79561-25-4 C14H18FNO4
FMOC-ASP(O-2-PHIPR)-OH FMOC-ASP(O-2-PHIPR)-OH 200336-86-3 C28H27NO6
H-PRO-NHET HCL H-PRO-NHET HCL 58107-62-3 C7H15ClN2O
(R)-2-METHYLCYSTEINE HYDROCHLORIDE (R)-2-METHYLCYSTEINE HYDROCHLORIDE 148766-37-4 C4H10ClNO2S
N-EPSILON-BENZOYL-L-LYSINE N-EPSILON-BENZOYL-L-LYSINE 1219-46-1 C13H18N2O3
TYRPHOSTIN AG 1288 TYRPHOSTIN AG 1288 116313-73-6 C10H5N3O4
3-HYDROXY-4-METHOXYBENZYLAMINE HYDROCHLORIDE 3-HYDROXY-4-METHOXYBENZYLAMINE HYDROCHLORIDE 42365-68-4 C8H12ClNO2
(R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(3-FLUORO-PHENYL)-PROPIONIC ACID C9H10FNO2
Z-GLN-GLY-OH Z-GLN-GLY-OH 6610-42-0 C15H19N3O6
Z-D-DAP(FMOC)-OH Z-D-DAP(FMOC)-OH 185968-90-5 C26H24N2O6
FMOC-N-OMEGA-NITRO-D-ARGININE FMOC-N-OMEGA-NITRO-D-ARGININE 160347-94-4 C21H23N5O6
BOC-BETA-(2-QUINOLYL)-D-ALA-OH BOC-BETA-(2-QUINOLYL)-D-ALA-OH 170157-64-9 C17H20N2O4
FMOC-D-ALLO-THR-OH FMOC-D-ALLO-THR-OH 130674-54-3 C19H19NO5
(S)-(+)-2-TERT-BUTYLAMINO-1-PHENYLETHAN& (S)-(+)-2-TERT-BUTYLAMINO-1-PHENYLETHAN& 14467-32-4 C12H19NO
DL-Aspartic acid magnesium salt tetrahydrate DL-Aspartic acid magnesium salt tetrahydrate 215528-79-3 C4H13MgNO8
N-Hexadecanoyl-L-phenlyalanine N-Hexadecanoyl-L-phenlyalanine 37571-96-3 C25H41NO3
FMOC-D-HYP(TBU)-OH FMOC-D-HYP(TBU)-OH 464193-92-8 C24H27NO5
N-CARBOBENZOXY-L-LEUCYL-L-ALANINE BENZYL ESTER N-CARBOBENZOXY-L-LEUCYL-L-ALANINE BENZYL ESTER 17664-94-7 C24H30N2O5
1-[(BENZYLOXY)CARBONYL]PYRROLIDINE-2-CARBOXYLIC ACID 1-[(BENZYLOXY)CARBONYL]PYRROLIDINE-2-CARBOXYLIC ACID 5618-96-2 C13H15NO4
Boc-L-Cyclobutylglycine Boc-L-Cyclobutylglycine 155905-77-4 C11H19NO4
N-(9-FLUORENYLMETHOXYCARBONYL)GLYCINE-1-13C-15N N-(9-FLUORENYLMETHOXYCARBONYL)GLYCINE-1-13C-15N 125700-33-6 C17H15NO4
L-ASPARATIC ACID-15N L-ASPARATIC ACID-15N 3715-16-0 C4H7NO4
FMOC-ORN(DDE)-OH FMOC-ORN(DDE)-OH 269062-80-8 C30H34N2O6
(S)-(+)-2-(DIBENZYLAMINO)-1-PROPANOL (S)-(+)-2-(DIBENZYLAMINO)-1-PROPANOL 60479-65-4 C17H21NO
L-ORNITHINE DIHYDROCHLORIDE L-ORNITHINE DIHYDROCHLORIDE 6211-16-1 C5H14Cl2N2O2
POLY-L-SERINE POLY-L-SERINE (C3H5NO2)n+H2O
FMOC-TYR(TBU)-OPFP FMOC-TYR(TBU)-OPFP 125043-03-0 C34H28F5NO5
N,N-BIS[2-(P-TOLYLSULFONYLOXY)ETHYL]-P-TOLUENESULFONAMIDE N,N-BIS[2-(P-TOLYLSULFONYLOXY)ETHYL]-P-TOLUENESULFONAMIDE 16695-22-0 C25H29NO8S3
D-ASPARAGINE METHYL ESTER HYDROCHLORIDE D-ASPARAGINE METHYL ESTER HYDROCHLORIDE 129902-07-4 C5H11ClN2O3
FMOC-D-CIS-HYP-OH FMOC-D-CIS-HYP-OH 214852-45-6 C20H19NO5
Fmoc-D-Asp-OtBu Fmoc-D-Asp-OtBu 34098-70-7 C23H25NO6
H-Thr(tBu)-OtBu.AcOH H-Thr(tBu)-OtBu.AcOH 5854-77-3 C12H25NO3.C2H4O2
N-ISOBUTYRYL-D-CYSTEINE N-ISOBUTYRYL-D-CYSTEINE 124529-07-3 C7H13NO3S
(R)-3-(3-HYDROXY-4-METHOXYPHENYL)-BETA-ALANINE
(R)-3-(3-HYDROXY-4-METHOXYPHENYL)-BETA-ALANINE 925221-88-1 C10H13NO4
METHYL N-BUTYLSULFONYL-L-P-HYDROXYPHENYLALANINE METHYL N-BUTYLSULFONYL-L-P-HYDROXYPHENYLALANINE 142374-01-4 C14H21NO5S
(±)-amino(2-fluorophenyl)acetic acid (±)-amino(2-fluorophenyl)acetic acid 84145-28-8 C8H8FNO2
trans-4-Phenyl-L-proline trans-4-Phenyl-L-proline 96314-26-0 C11H13NO2
(S)-3-(Fmoc-amino)-4-(3-chlorophenyl)butyric acid (S)-3-(Fmoc-amino)-4-(3-chlorophenyl)butyric acid C25H22ClNO4
(2r,3s)-3-Phenylpyrrolidine-2-Carboxylic Acid (2r,3s)-3-Phenylpyrrolidine-2-Carboxylic Acid 118758-50-2 C11H13NO2
DL-4-Cyanophenylalanine DL-4-Cyanophenylalanine 22888-47-7 C10H10N2O2
Blend amino acids powder Blend amino acids powder
D-Cyclohexylalanine hydrochloride D-Cyclohexylalanine hydrochloride 99065-30-2 C9H17NO2.HCl
Trityl-L-Alanine diethylammonium salt Trityl-L-Alanine diethylammonium salt 80514-65-4 C26H32N2O2
D-S-Isoamylcysteine D-S-Isoamylcysteine 312746-71-7 C8H17NO2S
5-Methyl-D-norleucine 5-Methyl-D-norleucine 138751-02-7 C7H15NO2
Furo[2,3-b]pyrazine-6-carboxylic acid, 7-amino-, ethyl ester (9CI) Furo[2,3-b]pyrazine-6-carboxylic acid, 7-amino-, ethyl ester (9CI) 187732-95-2 C9H9N3O3
(S)-(+)-2-AMINO-3-CYCLOHEXYL-1-PROPANOL HYDROCHLORIDE (S)-(+)-2-AMINO-3-CYCLOHEXYL-1-PROPANOL HYDROCHLORIDE 117160-99-3 C9H20ClNO
(R)-2-Amino-3-(diethylamino)propanoic acid (R)-2-Amino-3-(diethylamino)propanoic acid 739363-49-6 C7H16N2O2
Methyl-1-aminocyclohexane carboxylate (free base) Methyl-1-aminocyclohexane carboxylate (free base) 4507-57-7 C8H15NO2
(S)-3-Amino-3-(3-methyl-phenyl)-propionic acid (S)-3-Amino-3-(3-methyl-phenyl)-propionic acid 701907-44-0 C10H13NO2
(R)-3-Amino-3-(2-chloro-phenyl)-propionic acid (R)-3-Amino-3-(2-chloro-phenyl)-propionic acid 740794-79-0 C9H10ClNO2
(S)-3-Amino-3-(2-chloro-phenyl)-propionic acid (S)-3-Amino-3-(2-chloro-phenyl)-propionic acid 763922-37-8 C9H10ClNO2
N'-Laruoyl-L-lysine N'-Laruoyl-L-lysine 52315-75-0 C18H36N2O3
O-CRESOLSULFONPHTHALEIN-3',3''-BIS(METHYLAMINOACETIC ACID SODIUM SALT) O-CRESOLSULFONPHTHALEIN-3',3''-BIS(METHYLAMINOACETIC ACID SODIUM SALT) 4079-10-1 C27H28N2O9S
Epsilon-polylysine Epsilon-polylysine 28211-04-3 C8H18N2O
Ethyl 1-Boc-4-ethyl-4-piperidine carboxylate Ethyl 1-Boc-4-ethyl-4-piperidine carboxylate 188792-70-3 C15H27NO4
Fmoc-Phenylalanyl-glycine Fmoc-Phenylalanyl-glycine 169624-67-3 C26H24N2O5
tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate 145166-06-9 C11H21NO3
(S)-3-(Pyridine-3-yl)propyl-1-(3,3-dimethyl-2-oxo-pentanoyl)pyrrolidine-2-carboxylate (S)-3-(Pyridine-3-yl)propyl-1-(3,3-dimethyl-2-oxo-pentanoyl)pyrrolidine-2-carboxylate 186452-09-5 C20H28N2O4
BOC-ARG(BOC)2-OH BOC-ARG(BOC)2-OH 97745-69-2 C21H38N4O8
PHENYLAC-GLN-OH PHENYLAC-GLN-OH 28047-15-6 C13H16N2O4
L-NORVALINOL L-NORVALINOL 22724-81-8 C5H13NO
GAMMA-METHYL-L-LEUCINE GAMMA-METHYL-L-LEUCINE 106247-35-2 C7H15NO2
BOC-D-DAB(ALOC)-OH DCHA BOC-D-DAB(ALOC)-OH DCHA 350820-59-6 C25H45N3O6
N-BENZYL-L-PROLINE ETHYL ESTER N-BENZYL-L-PROLINE ETHYL ESTER 955-40-8 C14H19NO2
10-Propargyl-10-deazaaminopterin 10-Propargyl-10-deazaaminopterin 146464-95-1 C23H23N7O5
H-DL-PRO-OME HCL H-DL-PRO-OME HCL 79397-50-5 C6H12ClNO2
(R)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID (R)-3-AMINO-3-(3-METHYL-PHENYL)-PROPIONIC ACID C10H13NO2
AC-GLU-OME AC-GLU-OME 17015-15-5 C8H13NO5
2,6-DIISOCYANATOHEXANOIC ACID 2-ISOCYANATOETHYL ESTER 2,6-DIISOCYANATOHEXANOIC ACID 2-ISOCYANATOETHYL ESTER 69878-18-8 C11H13N3O5
N-ME-PHG-OH N-ME-PHG-OH 2611-88-3 C9H11NO2
BOC-(S)-3-AMINO-3-(2-METHYL-PHENYL)-PROPIONIC ACID BOC-(S)-3-AMINO-3-(2-METHYL-PHENYL)-PROPIONIC ACID C15H21NO4
FMOC-NLE-OSU FMOC-NLE-OSU 201026-08-6 C25H26N2O6
tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate tert-Butyl (2S)-2-(hydroxymethyl)-5-oxopyrrolidine-1-carboxylate 81658-25-5 C10H17NO4
H-HYP(BZL)-OME HCL H-HYP(BZL)-OME HCL 66831-17-2 C13H18ClNO3
H-D-PHE-OET HCL H-D-PHE-OET HCL 63060-94-6 C11H16ClNO2
(S)-N-FMOC-OCTYLGLYCINE (S)-N-FMOC-OCTYLGLYCINE 193885-59-5 C25H31NO4
S-(4-NITROPHENYL)-L-CYSTEINE S-(4-NITROPHENYL)-L-CYSTEINE 55288-30-7 C9H10N2O4S
BOC-4-ABZ-OH BOC-4-ABZ-OH 66493-39-8 C12H15NO4
L-Homoserine hydrochloride L-Homoserine hydrochloride 196950-52-4 C4H10ClNO3
METHYL 6-AMINO-1H-INDOLE-2-CARBOXYLATE METHYL 6-AMINO-1H-INDOLE-2-CARBOXYLATE 167027-30-7 C10H10N2O2
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