103067-78-3

Basic information

• Product Name: (R)- 2-(3'-butenyl) glycine
• Synonyms: (R)- 2-(3'-butenyl) glycine;(R)-2-Aminohex-5-enoic acid
• CAS NO: 103067-78-3
• Molecular Formula: C₆H₁₁NO₂
• Molecular Weight: 129.15704
• Mol File: 103067-78-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: (R)- 2-(3'-butenyl) glycine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)- 2-(3'-butenyl) glycine(103067-78-3)
• EPA Substance Registry System: (R)- 2-(3'-butenyl) glycine(103067-78-3)

Safety Data

• Hazardous Substances Data: 103067-78-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
(R)-2-(3'-butenyl) glycine is used as a therapeutic agent for its potential antioxidant and neuroprotective properties, which may contribute to the treatment of various neurological disorders.
Used in Food Industry:
(R)-2-(3'-butenyl) glycine is used as a natural flavoring agent, adding unique taste profiles to food products while maintaining a natural ingredient label.

Upstream product

• 774174-32-2 (R)-2-amino-5-hexenoic acid amide 
• 114486-35-0 Methyl 2-aminohex-5-enoate 
• 16258-05-2 D,L-2-amino-5-hexenoic acid 
• 188194-81-2 2-amino-5-hexenoic acid amide 
• 33574-02-6 cyclopropylmethyl iodide 
• 170115-96-5 2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide 

Downstream Products

• 188195-01-9 (R)-2-(Acryloyl-benzyl-amino)-hex-5-enoic acid methyl ester 
• 188195-02-0 (R)-2-[Allyl-(4-methoxy-benzyl)-amino]-hex-5-enoic acid methyl ester 

Relevant articles and documents

Large scale enantiomeric synthesis, purification, and characterization of ω-unsaturated amino acids via a Gly-Ni(II)-BPB-complex

The enantiomeric syntheses of ω-unsaturated amino acids and β-substituted ω-unsaturated amino acids were accomplished by using Gly-Ni-2[N-(N′-benzylprolyl)amino]benzophenone (BPB) as a chiral auxiliary. The synthesis provides excellent yields and high diastereoselectivities. The product crystallization followed by isomer epimerization strategy makes the reaction practical and useful for large-scale preparations. Dialkylation of the Ni(II)-complex, which was designed for mechanistic considerations, revealed that high diastereoselectivity is obtained due to the thermodynamic conformational stability of the Ni(II)-complex. The assignment of absolute configuration was accomplished by NMR, which is supported by corresponding X-ray structure and optical rotation data. Both enantiomerically pure amino acids can be synthesized in this alkylation-hydrolysis two-step strategy in multi gram scales.

A Biocatalytic Route to Enantiomerically Pure Unsaturated α-H-α-Amino Acids

A set of both enantiomeric forms of non-proteinogenic, unsaturated α-H-α-amino acids was efficiently synthesized using a biocatalytic pathway. This route involved the straightforward synthesis of the required unsaturated amino acid amides, followed by resolution with an aminopeptidase present in Pseudomonas putida ATCC 12633 and/or a genetically modified organism, leading to the (S)-acids and (R)-amides. Undesired amino acid racemase activity was identified in the wild-type strain, which was absent in the newly developed organism. The (R)-amides were hydrolyzed under mild conditions using an amidase present in whole cells from Rhodococcus erythropolis NCIMB 11540 to the (R)-acids. The viability of this procedure was demonstrated with the multi-gram synthesis of a variety of unsaturated amino acids in excellent enantiopurity.

Ruthenium-catalyzed ring closing olefin metathesis of non-natural α-amino acids

The use of various enantiopure amino acid-derived diolefins as substrates for the ring closing olefin metathesis reaction (RCM) has been investigated. This reaction has been shown to be an efficient transformation for providing highly functionalized 6- and 7-membered ring amino acids.