346707-82-2

Usage

Chirality

Chiral compound, with the (2R)-enantiomer being the naturally occurring form

Derivative of

Amino acid alanine

Structure

Contains a six-carbon chain with a triple bond at the fourth carbon and an amino group attached to the second carbon

Applications

Used in organic synthesis and pharmaceutical research as a building block for the creation of various compounds and drugs

Field of interest

Chemical and pharmaceutical sciences

Upstream product

• 771466-51-4 (R)-2-amino-4-hexynoic acid amide 
• 859842-16-3 2-(benzhydrylidene-amino)-hex-4-ynoic acid methyl ester 
• 346707-79-7 rac-2-amino-4-hexynoic acid amide 

Downstream Products

• 346707-86-6 (S)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 2-hydroxymethylbenzyl ester 
• 441018-79-7 (S)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 3-hydroxymethylbenzyl ester 
• 346707-74-2 (R)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 3-hydroxymethylbenzyl ester 
• 346707-62-8 (S)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 3-((S)-2-tert-butoxycarbonylamino-hex-4-ynoyloxy)benzyl ester 
• 346707-65-1 (R)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 3-((R)-2-tert-butoxycarbonylamino-hex-4-ynoyloxy)benzyl ester 
• 346707-61-7 (S)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 2-((S)-2-tert-butoxycarbonylamino-hex-4-ynoyloxy)benzyl ester 
• 346707-64-0 (R)-2-tert-butoxycarbonylamino-hex-4-ynoic acid 2-((R)-2-tert-butoxycarbonylamino-hex-4-ynoyloxy)benzyl ester 

Relevant academic research and scientific papers

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.