Intramolecular Stereoselective Stetter Reaction Catalyzed by Benzaldehyde Lyase

Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9326-9329. doi: 10.1002/anie.202100534. Epub 2021 Mar 12.

Abstract

The reliable design and prediction of enzyme promiscuity to access transformations not observed in nature remains a long-standing challenge. Herein, we present the first example of an intramolecular stereoselective Stetter reaction catalyzed by benzaldehyde lyase, guided by the rational structure screening of various ThDP-dependent enzymes using molecular dynamics (MD) simulations. After optimization, high productivity (up to 99 %) and stereoselectivity (up to 99:1 e.r.) for this novel enzyme function was achieved.

Keywords: Stetter reaction; benzaldehyde lyase; enantioselectivity; enzyme catalysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetic Acid
  • Aldehyde-Lyases / metabolism*
  • Biocatalysis
  • Esters / chemistry
  • Esters / metabolism*
  • Molecular Dynamics Simulation
  • Molecular Structure
  • Pseudomonas fluorescens / enzymology
  • Stereoisomerism
  • Thiamine Pyrophosphate / metabolism

Substances

  • Esters
  • Aldehyde-Lyases
  • benzaldehyde lyase
  • Acetic Acid
  • Thiamine Pyrophosphate