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

Description

L-Allylglycine is a white to off-white crystalline powder that serves as a glutamic acid decarboxylase inhibitor. L-Allylglycine plays a significant role in various applications across different industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
L-Allylglycine is used as a pharmaceutical compound for its inhibitory effects on glutamic acid decarboxylase. This inhibition can be beneficial in the development of treatments for various neurological disorders and conditions related to the excitatory neurotransmission of glutamate.
Used in Chemical Synthesis:
L-Allylglycine, with its unique chemical structure, is used as a building block in the synthesis of various organic compounds. Its ability to inhibit glutamic acid decarboxylase makes it a valuable starting material for the development of new drugs and pharmaceutical agents.
Used in Research and Development:
In the field of research and development, L-Allylglycine is utilized as a research tool to study the role of glutamic acid decarboxylase in various biological processes. This understanding can lead to the discovery of novel therapeutic approaches and the development of new drugs targeting this enzyme.
Used in Neurological Applications:
L-Allylglycine is used as a therapeutic agent for neurological applications, particularly in the treatment of conditions involving excessive glutamate activity, such as epilepsy, neuropathic pain, and certain neurodegenerative diseases. Its inhibitory action on glutamic acid decarboxylase can help regulate glutamate levels and provide relief from these conditions.

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

• 144073-06-3 α-allylglycine amide 
• 100-52-7 benzaldehyde 
• 145275-96-3 2-Amino-N-methoxy-4-pentenamide 
• 100516-55-0 (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 145275-97-4 2-Amino-N-methoxy-4-pentenamide formate 
• 125443-73-4 2-[(1R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-pent-4-enoic acid cyclohexyl ester 
• 125424-03-5 2-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pent-4-enoic acid cyclohexyl ester 
• 125424-01-3 2-[(1R,4R)-1,7,7-Trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-pent-4-enoic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 125424-02-4 2-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pent-4-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 125424-02-4 2-[(1S,2S,5S)-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 
• 125424-02-4 2-[(1R,2R,5R)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pent-4-enoic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 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 
• 135263-84-2 (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (2S)-2-<(tert-butoxycarbonyl)amino>pent-4-enoate 
• 307304-61-6 (2R,4'R,5'S)-2-amino-1-(3',4'-dimethyl-2'-oxo-5'-phenyl-1'-imidazolydinyl)-4-penten-1-one 

Downstream Products

• 50299-15-5 methyl (S)-allylglycinate 
• 78553-51-2 (S)-2-(benzyloxycarbonylamino)pent-4-enoic acid 
• 89985-87-5 methyl (2S)-2-tert-butoxycarbonylamino-4-pentenoate 
• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 141044-54-4 Boc-Alg-D-Val-ONb 
• 124593-83-5 L-phenoxyacetyl allylglycine 
• 110579-31-2 (2S)-N-para-toluenesulfonylvinylglycine 
• 323196-01-6 N-phenylfluorenyl-(S)-2-amino-4-pentenoic acid 
• 146549-21-5 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid 
• 874384-01-7 benzyl (S)-2-(dibenzylamino)pent-4-enoate 
• 916049-29-1 5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester 
• 868754-29-4 2-tert-butoxycarbonylamino-hexanedioic acid 6-cyclohexyl ester 
• 868754-92-1 (E)-(S)-5-tert-Butoxycarbonylamino-hex-2-enedioic acid 6-benzyl ester 1-cyclohexyl ester 
• 124097-05-8 benzyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-pentenoate 

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.