16338-48-0

Basic information

• Product Name: L-Allylglycine
• Synonyms: (S)-(-)-2-AMINO-4-PENTENOIC ACID;(S)-2-AMINO-4-PENTENOIC ACID;RARECHEM BK PT 0249;3-VINYL-L-ALANINE;L-C-ALLYLGLYCINE;L-ALPHA-ALLYL-GLY;L-ALPHA-ALLYL-GLYCINE;H-(ALLYL)GLY-OH
• CAS NO: 16338-48-0
• Molecular Formula: C₅H₉NO₂
• Molecular Weight: 115.13
• Product Categories: Pharmaceutical Raw Materials;Amino Acids;Unusual amino acids;Chiral Reagent;Chiral Compound;a-amino;unnatural amino acids
• Mol File: 16338-48-0.mol
• Article Data: 19

Chemical Properties

• Melting Point: 283 °C (dec.)(lit.)
• Boiling Point: 215.41°C (rough estimate)
• Flash Point: 93.5 °C
• Appearance: white/powder
• Density: 1.1808 (rough estimate)
• Vapor Pressure: 0.0226mmHg at 25°C
• Refractive Index: 1.4538 (estimate)
• Storage Temp.: 2-8°C
• Solubility: H2O: 100 mg/mL
• PKA: 2.22±0.10(Predicted)
• Water Solubility: soluble
• BRN: 1721512
• CAS DataBase Reference: L-Allylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: L-Allylglycine(16338-48-0)
• EPA Substance Registry System: L-Allylglycine(16338-48-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• Hazardous Substances Data: 16338-48-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white crystalline powder

Uses

L-Allylglycine is a glutamic acid decarboxylase inhibitor.

InChI:InChI=1/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)/t4-/m0/s1

Upstream product

• 145275-96-3 2-Amino-N-methoxy-4-pentenamide 
• 556-56-9 allyl iodid 
• 340039-87-4 C₁₅H₂₂N₂O₂S₂ 
• 106-95-6 allyl bromide 
• 500137-55-3 (1S,2R,8R)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]-undec-6-en-4-one 
• 124302-98-3 (N-{phenyl[2-(pyridine-2-carboxamido)phenyl]methylidene}glycinato-N,N',N'',O)nickel(II) 
• 133773-64-5 (RS)-N-(benzyloxycarbonyl)-2-amino-4-pentenoic acid 
• 1069-48-3 rac-allylglycine 
• 225938-47-6 <1R(S),2R>-N-(2-hydroxy-1-methyl-2-phenethyl)-2-amino-N-methyl-4-pentenamide 
• 565237-60-7 (3R,6S)-3-allyl-6-tert-butyl-5-methoxy-6-methyl-3,6-dihydro-2H-1,4-oxazin-2-one 
• 56-40-6 glycine 
• 307304-61-6 (2R,4'R,5'S)-2-amino-1-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-4-penten-1-one 
• 135263-84-2 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2S)-2-<(tert-butoxycarbonyl)amino>pent-4-enoate 
• 125424-02-4 2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pent-4-enoic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 

Downstream Products

• 110579-31-2 (2S)-N-para-toluenesulfonylvinylglycine 
• 146549-21-5 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid 
• 364784-17-8 N-tert-butoxycarbonyl-L-allylglycyl-L-prolyl-α-aminoisobutyryl-C^α-methyl-L-allylglycine benzylamide 
• 178859-60-4 (S)-2-Oxo-6-[(E)-(3-phenyl-acryloyl)amino]-heptanedioic acid dimethyl ester 
• 178859-61-5 (S)-2-Oxo-6-(3-phenyl-propionylamino)-heptanedioic acid dimethyl ester 
• 178859-58-0 (S)-2-Benzyloxycarbonylamino-6-oxo-heptanedioic acid dimethyl ester 
• 824394-11-8 (2S,5'S)-2-amino-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid 
• 824394-11-8 (2S,5'R)-2-amino-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid 
• 156426-54-9 (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid 
• 156426-53-8 (2S,5'R)-2-(N-(benzyloxycarbonyl)amino)-3-(3-carboxy-2-isoxazolin-5-yl)propanoic acid 
• 156426-52-7 methyl (2S,5'S)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate 
• 156426-51-6 methyl (2S,5'R)-2-(N-(benzyloxycarbonyl)amino)-3-(3-(methoxycarbonyl)-2-isoxazolidin-5-yl)propanoate 

Relevant articles and documents

Phase-transfer enantioselective monoalkylation of prochiral nickel(ii) complexes catalyzed by 3,3′-bis[hydroxy(diphenyl)methyl]-1,1′- binaphthyl-2,23′-diol (BIMBOL) as a route to α-amino acids

An achiral nickel complex with a Schiff base derived from glycine was alkylated with alkyl halides under conditions of asymmetric phase-transfer catalysis. The chiral tetraol (R)-BIMBOL was employed as a catalyst. The enantiomeric purity of the alkylation products was up to 88%. Subsequent decomposition of the complexes afforded the corresponding a-amino acids.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Microbial enantioselective removal of the N-benzyloxycarbonyl amino protecting group

In order to deprotect N-carbobenzoxy-l-aminoacids (Cbz-AA) and related compounds, a series of microorganisms was selected from soil by enrichment cultures with Cbz-l-Glu as sole nitrogen source. A lyophilized whole-cell preparation of two Arthrobacter sp. strains grown on Cbz-Glu or Cbz-Gly exhibited a high cleavage activity. The conditions of hydrolysis have been optimized and a quantitative enantioselective deprotection of several Cbz-dl-amino acids was obtained, as well as the deprotection of N-carbamoylester derivatives of several synthetic amino compounds. The preparation of Cbz-d-allylglycine and l-allylglycine in high yield and high optical purity is described as an application of this method.