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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
FMOC-(S)-3-AMINO-4-(2-METHYL-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(2-METHYL-PHENYL)-BUTYRIC ACID 270062-91-4 C26H25NO4
H-VAL-ALA-OH H-VAL-ALA-OH 27493-61-4 C8H16N2O3
FMOC-(R)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID 269396-73-8 C25H22INO4
FMOC-(R)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID FMOC-(R)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID 479064-95-4 C24H20FNO4
H-ALA-AMC TFA H-ALA-AMC TFA 96594-10-4 C15H15F3N2O5
trans-(1R,2R)-2-Aminocyclopentanol hydrochloride trans-(1R,2R)-2-Aminocyclopentanol hydrochloride 31775-67-4 C5H12ClNO
D-Aspartic acid 4-tert-butyl ester D-Aspartic acid 4-tert-butyl ester 64960-75-4 C8H15NO4
H-MET-NH2 H-MET-NH2 4510-08-1 C5H12N2OS
PHTHALOYL-L-GLUTAMIC ANHYDRIDE PHTHALOYL-L-GLUTAMIC ANHYDRIDE 25830-77-7 C13H9NO5
BOC-(S)-3-AMINO-4-(2-THIENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(2-THIENYL)-BUTYRIC ACID 190190-47-7 C13H19NO4S
(S)-3-AMINO-3-(3-NITRO-PHENYL)-PROPIONIC ACID (S)-3-AMINO-3-(3-NITRO-PHENYL)-PROPIONIC ACID 734529-57-8 C9H10N2O4
GLYCYL-DL-TRYPTOPHAN GLYCYL-DL-TRYPTOPHAN 2189-26-6 C13H15N3O3
BOC-(S)-3-AMINO-4-(3-BENZOTHIENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-BENZOTHIENYL)-BUTYRIC ACID 270063-45-1 C17H21NO4S
BOC-(S)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(1-NAPHTHYL)-BUTYRIC ACID 219297-09-3 C19H23NO4
trans-4-Phenyl-L-proline hydrochloride trans-4-Phenyl-L-proline hydrochloride 90657-53-7 C11H14ClNO2
DL-PROPARGYLGLYCINE DL-PROPARGYLGLYCINE 64165-64-6 C5H7NO2
BOC-(R)-3-AMINO-5-HEXENOIC ACID BOC-(R)-3-AMINO-5-HEXENOIC ACID 269726-94-5 C11H19NO4
4-DIMETHYLAMINO-1-BUTANOL 4-DIMETHYLAMINO-1-BUTANOL 13330-96-6 C6H15NO
FMOC-(R)-3-AMINO-4-(3-METHYL-PHENYL)-BUTYRIC ACID FMOC-(R)-3-AMINO-4-(3-METHYL-PHENYL)-BUTYRIC ACID 269398-84-7 C26H25NO4
3-(4-Nitrophenyl)-beta-alanine 3-(4-Nitrophenyl)-beta-alanine 102308-62-3 C9H10N2O4
DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE DL-PHENYLALANINE METHYL ESTER HYDROCHLORIDE 5619-07-8 C10H14ClNO2
H-D-PHE-OTBU HCL H-D-PHE-OTBU HCL 3403-25-6 C13H20ClNO2
D-CYSTEINE HYDROCHLORIDE D-CYSTEINE HYDROCHLORIDE 207121-46-8 C3H10ClNO3S
4-FLUORO-DL-TRYPTOPHAN 4-FLUORO-DL-TRYPTOPHAN 25631-05-4 C11H11FN2O2
Boc-(S)-3-Amino-3-(4-methylphenyl)propionic acid Boc-(S)-3-Amino-3-(4-methylphenyl)propionic acid 479064-96-5 C15H21NO4
3-AMINOBENZOIC ACID HYDROCHLORIDE 3-AMINOBENZOIC ACID HYDROCHLORIDE 15151-51-6 C7H8ClNO2
(-)-(1R,3S)-N-Boc-3-Aminocyclopentanecarboxylic acid (-)-(1R,3S)-N-Boc-3-Aminocyclopentanecarboxylic acid 161660-94-2 C11H19NO4
ETHYL 2-AMINO-3-HYDROXYPROPANOATE HYDROCHLORIDE ETHYL 2-AMINO-3-HYDROXYPROPANOATE HYDROCHLORIDE 3940-27-0 C5H12ClNO3
4-(tert-ButoxycarbonylaMino)-1-butanol 4-(tert-ButoxycarbonylaMino)-1-butanol 75178-87-9 C9H19NO3
BOC-L-BETA-HOMOSERINE(OBZL) BOC-L-BETA-HOMOSERINE(OBZL) 218943-31-8 C16H23NO5
3-Pyridylalanine 3-Pyridylalanine 17470-24-5 C8H10N2O2
H-PHG-OME HCL H-PHG-OME HCL 13226-98-7 C9H12ClNO2
(S)-3-AMINO-4-(2-NAPHTHYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(2-NAPHTHYL)BUTANOIC ACID HYDROCHLORIDE 270063-39-3 C14H15NO2
CHLOROACETYL-DL-VALINE CHLOROACETYL-DL-VALINE 4090-17-9 C7H12ClNO3
BOC-(S)-3-AMINO-4-(3,4-DIFLUORO-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3,4-DIFLUORO-PHENYL)-BUTYRIC ACID 270063-54-2 C15H19F2NO4
(S)-3-AMINO-4-(3-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-FLUOROPHENYL)BUTANOIC ACID HYDROCHLORIDE 270596-50-4 C10H12FNO2
FMOC-L-ALANINOL FMOC-L-ALANINOL 161529-13-1 C18H19NO3
BOC-HOMO-L-TYROSINE BOC-HOMO-L-TYROSINE 198473-94-8 C15H21NO5
N-CARBOBENZOXY-L-PHENYLALANYL-L-PHENYLALANINE N-CARBOBENZOXY-L-PHENYLALANYL-L-PHENYLALANINE 13122-91-3 C26H26N2O5
(+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID 151907-80-1 C11H17NO4
AMINO-(3-FLUORO-PHENYL)-ACETIC ACID AMINO-(3-FLUORO-PHENYL)-ACETIC ACID 7292-74-2 C8H8FNO2
FMOC-(S)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID FMOC-(S)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID 270065-72-0 C25H22INO4
N-CBZ-DL-TRYPTOPHAN N-CBZ-DL-TRYPTOPHAN 13058-16-7 C19H18N2O4
FMOC-L-BETA-HOMOLYSINE(BOC) FMOC-L-BETA-HOMOLYSINE(BOC) 203854-47-1 C27H34N2O6
Sodium L-aspartate Sodium L-aspartate 5598-53-8 C4H5MgNO4
(R)-N-Boc-glutamic acid-1,5-dimethyl ester (R)-N-Boc-glutamic acid-1,5-dimethyl ester 59279-60-6 C12H21NO6
tert-butyl 5-oxo-L-prolinate tert-butyl 5-oxo-L-prolinate 35418-16-7 C9H15NO3
(S)-4-Boc-Piperazine-3-carboxylic acid (S)-4-Boc-Piperazine-3-carboxylic acid 159532-59-9 C10H18N2O4
N-CBZ-L-PROLINE TERT-BUTYL ESTER N-CBZ-L-PROLINE TERT-BUTYL ESTER 16881-39-3 C17H23NO4
BOC-THR(BZL)-OL BOC-THR(BZL)-OL 133565-43-2 C16H25NO4
5-hydroxy-l-tryptophan 5-hydroxy-l-tryptophan 314062-44-7 C11H12N2O3
DL-ALANYL-DL-VALINE DL-ALANYL-DL-VALINE 1999-46-8 C8H16N2O3
BOC-ARG(MTS)-OH BOC-ARG(MTS)-OH 102185-38-6 C21H34N4O7S
3-CHLORO-L-ALANINE HYDROCHLORIDE 3-CHLORO-L-ALANINE HYDROCHLORIDE 51887-89-9 C3H7Cl2NO2
4-BORONO-L-PHENYLALANINE 4-BORONO-L-PHENYLALANINE 76410-58-7 C9H12BNO4
BOC-(S)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 270065-77-5 C16H20F3NO4
P-AMINO-DL-PHENYLALANINE P-AMINO-DL-PHENYLALANINE 2922-41-0 C9H12N2O2
DL-2'-METHYLPHENYLALANINE HYDROCHLORIDE DL-2'-METHYLPHENYLALANINE HYDROCHLORIDE 22888-51-3 C10H13NO2
(2-FLUOROPHENYL)GLYCINE (2-FLUOROPHENYL)GLYCINE 2343-27-3 C8H8FNO2
N-CARBOBENZOXY-DL-NORVALINE N-CARBOBENZOXY-DL-NORVALINE 21691-43-0 C13H17NO4
H-ASP(OBZL)-OBZL HCL H-ASP(OBZL)-OBZL HCL 6327-59-9 C18H20ClNO4
N-2-NITROPHENYLSULFENYL-L-VALINE DICYCLOHEXYLAMMONIUM SALT N-2-NITROPHENYLSULFENYL-L-VALINE DICYCLOHEXYLAMMONIUM SALT 7675-57-2 C23H37N3O4S
BOC-TYR(ET)-OH BOC-TYR(ET)-OH 76757-91-0 C16H23NO5
H-D-LEU-NH2 HCL H-D-LEU-NH2 HCL 80970-09-8 C6H15ClN2O
FMOC-(R)-3-AMINO-5-PHENYLPENTANOIC ACID FMOC-(R)-3-AMINO-5-PHENYLPENTANOIC ACID 269398-87-0 C26H25NO4
BOC-(R)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(4-IODO-PHENYL)-BUTYRIC ACID 269396-71-6 C15H20INO4
(S)-3-AMINO-5-PHENYLPENTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-5-PHENYLPENTANOIC ACID HYDROCHLORIDE 218278-62-7 C11H15NO2
(R)-3-AMINO-4-(4-IODOPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-IODOPHENYL)BUTANOIC ACID HYDROCHLORIDE 269396-70-5 C10H12INO2
L-ISOLEUCINOL HCL L-ISOLEUCINOL HCL 133736-94-4 C6H16ClNO
N-ALPHA-ACETYL-L-ARGININE N-ALPHA-ACETYL-L-ARGININE 155-84-0 C8H16N4O3
(R)-2-Amino-2-methyl-4-pentenoic acid (R)-2-Amino-2-methyl-4-pentenoic acid 96886-55-4 C6H11NO2
BOC-MET-OH DCHA BOC-MET-OH DCHA 22823-50-3 C22H42N2O4S
(S)-3-AMINO-4-(3-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE (S)-3-AMINO-4-(3-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE 270065-76-4 C11H12F3NO2
L-HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE L-HISTIDINE MONOHYDROCHLORIDE MONOHYDRATE 7048-02-4 C6H12ClN3O3
BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(2-TRIFLUOROMETHYL-PHENYL)-BUTYRIC ACID 269396-77-2 C16H20F3NO4
FMOC-ASP-OME FMOC-ASP-OME 145038-52-4 C20H19NO6
4-CHLORO-D-PHENYLALANINE HYDROCHLORIDE 4-CHLORO-D-PHENYLALANINE HYDROCHLORIDE 147065-05-2 C9H11Cl2NO2
O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER 1872-59-9 C16H23NO5
N-Cbz-L-homoserine lactone N-Cbz-L-homoserine lactone 35677-89-5 C12H13NO4
N-Butylsulfonyl-O-(4-(4-pyridinyl)butyl)-L-tyrosine N-Butylsulfonyl-O-(4-(4-pyridinyl)butyl)-L-tyrosine 149490-61-9 C22H30N2O5S
D-4-TERT-BUTYL-PHE D-4-TERT-BUTYL-PHE 274262-82-7 C13H19NO2
BOC-(R)-3-AMINO-4-(4-METHYL-PHENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(4-METHYL-PHENYL)-BUTYRIC ACID 269398-85-8 C16H23NO4
TERT-BUTOXYCARBONYLAMINO-PHENYL-ACETIC ACID TERT-BUTOXYCARBONYLAMINO-PHENYL-ACETIC ACID 3601-66-9 C13H17NO4
3-DIETHYLAMINO-1-PROPANOL 3-DIETHYLAMINO-1-PROPANOL 622-93-5 C7H17NO
(R)-3-AMINO-4-(4-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE (R)-3-AMINO-4-(4-TRIFLUOROMETHYLPHENYL)BUTANOIC ACID HYDROCHLORIDE 269726-76-3 C11H12F3NO2
BOC-(S)-3-AMINO-4-(3-METHYL-PHENYL)-BUTYRIC ACID BOC-(S)-3-AMINO-4-(3-METHYL-PHENYL)-BUTYRIC ACID 270062-93-6 C16H23NO4
S-CARBOXYMETHYL-L-CYSTEINE S-CARBOXYMETHYL-L-CYSTEINE 186537-58-6 C22H24N2O8S2
BOC-(S)-3-AMINO-5-HEXENOIC ACID BOC-(S)-3-AMINO-5-HEXENOIC ACID 270263-03-1 C11H19NO4
4-DIETHYLAMINO-2-BUTYN-1-OL 4-DIETHYLAMINO-2-BUTYN-1-OL 10575-25-4 C8H15NO
BOC-(4-AMINOMETHYL)-CYCLOHEXANE-CARBOXYLIC ACID BOC-(4-AMINOMETHYL)-CYCLOHEXANE-CARBOXYLIC ACID 162046-58-4 C13H23NO4
(S)-3-Amino-4-(2-chlorophenyl)butyric acid hydrochloride (S)-3-Amino-4-(2-chlorophenyl)butyric acid hydrochloride 270596-36-6 C10H12ClNO2
(1R,2R)-(-)-TRANS-1-AMINO-2-INDANOL (1R,2R)-(-)-TRANS-1-AMINO-2-INDANOL 163061-73-2 C9H11NO
BOC-(R)-3-AMINO-4-(3-BENZOTHIENYL)-BUTYRIC ACID BOC-(R)-3-AMINO-4-(3-BENZOTHIENYL)-BUTYRIC ACID 190190-48-8 C17H21NO4S
FMOC-CHG-OH FMOC-CHG-OH 161321-36-4 C23H25NO4
BOC-D-3,4,5-TRIFLUOROPHENYLALANINE BOC-D-3,4,5-TRIFLUOROPHENYLALANINE 205445-55-2 C14H16F3NO4
BOC-D-LYS(Z)-OH BOC-D-LYS(Z)-OH 76477-42-4 C31H51N3O6
BOC-(R)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID BOC-(R)-3-AMINO-3-(4-FLUORO-PHENYL)-PROPIONIC ACID 479064-94-3 C14H18FNO4
PTH-LEUCINE PTH-LEUCINE 4399-40-0 C13H16N2OS
BOC-D-CYCLOPROPYLALANINE-DCHA BOC-D-CYCLOPROPYLALANINE-DCHA 89483-09-0 C23H42N2O4
FMOC-D-CHG-OH FMOC-D-CHG-OH 198543-96-3 C23H25NO4
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