EnantioselectiveReduction of α,β-Dehydro-α-amidoCarboxylic Acid Derivatives by Ene-Reductases

Abstract Enantioselective reduction of α,β-dehydro-α-amido carboxylic acid derivatives to optically active amido carboxylic acid derivatives has been carried out using whole-cell overexpressing ene-reductases (EREDs). The reduced products were obtained with good yields and excellent enantiomeric excesses of >99%. Among the enzymes tested, Seqenzym ene-reductase E4671 proved to be the most effective, accommodating methyl ester, free amide, and diverse N-protecting groups, as well as β-unsubstituted, β-methyl, and β-ethyl substituted substrates. Notably, the reaction is readily scalable.

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Publication Details

Journal
Organic Letters
Published
2026-08-03
DOI
https://doi.org/10.1021/acs.orglett.6c02939
Primary Topic
Enzyme Catalysis and Immobilization
Type
article
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article

EnantioselectiveReduction of α,β-Dehydro-α-amidoCarboxylic Acid Derivatives by Ene-Reductases

Dominique Cahard, Janine Cossy, Julien Boutet, Pierre Gilles et al.
Organic Letters
Enzyme Catalysis and Immobilization
article

EnantioselectiveReduction of α,β-Dehydro-α-amidoCarboxylic Acid Derivatives by Ene-Reductases

Dominique Cahard, Janine Cossy, Julien Boutet, Pierre Gilles, Nicolas Marie
article en

Abstract

Abstract Enantioselective reduction of α,β-dehydro-α-amido carboxylic acid derivatives to optically active amido carboxylic acid derivatives has been carried out using whole-cell overexpressing ene-reductases (EREDs). The reduced products were obtained with good yields and excellent enantiomeric excesses of >99%. Among the enzymes tested, Seqenzym ene-reductase E4671 proved to be the most effective, accommodating methyl ester, free amide, and diverse N-protecting groups, as well as β-unsubstituted, β-methyl, and β-ethyl substituted substrates. Notably, the reaction is readily scalable.

Organic Letters
Centre National de la Recherche Scientifique (FR), George Washington University (US), Normandie Université (FR), Université de Rouen Normandie (FR), Institut National des Sciences Appliquées Rouen Normandie (FR), ESPCI Paris (FR)
Openalex Percentile: Top 15%
Enzyme Catalysis and Immobilization
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