Issue 82, 2023

Hydroxynitrile lyase engineering for promiscuous asymmetric Henry reaction with enhanced conversion, enantioselectivity and catalytic efficiency

Abstract

Arabidopsis thaliana hydroxynitrile lyase (AtHNL) engineering has uncovered variants that showed up to 12-fold improved catalytic efficiency than the wild-type towards asymmetric Henry reaction. The AtHNL variants have displayed excellent enantioselectivity, up to >99%, and higher conversion in the synthesis of 13 different (R)-β-nitroalcohols from their corresponding aldehydes. Using cell lysates of Y14M/F179W, we demonstrated a preparative scale synthesis of (R)-1-(4-methoxyphenyl)-2-nitroethanol, a tembamide chiral intermediate, in >99% ee and 52% yield.

Graphical abstract: Hydroxynitrile lyase engineering for promiscuous asymmetric Henry reaction with enhanced conversion, enantioselectivity and catalytic efficiency

Supplementary files

Article information

Article type
Communication
Submitted
13 Jun 2023
Accepted
15 Sep 2023
First published
20 Sep 2023

Chem. Commun., 2023,59, 12274-12277

Hydroxynitrile lyase engineering for promiscuous asymmetric Henry reaction with enhanced conversion, enantioselectivity and catalytic efficiency

B. V. Priya, D. H. S. Rao, A. Chatterjee and S. K. Padhi, Chem. Commun., 2023, 59, 12274 DOI: 10.1039/D3CC02837B

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