Enantioselective Sulfoxidation of Thioanisole by Cascading a Choline Oxidase and a Peroxygenase in the Presence of Natural Deep Eutectic Solvents

Chempluschem. 2020 Jan;85(1):254-257. doi: 10.1002/cplu.201900751.

Abstract

A bienzymatic cascade for selective sulfoxidation is presented. The evolved recombinant peroxygenase from Agrocybe aegeritra catalyses the enantioselective sulfoxidation of thioanisole whereas the choline oxidase from Arthrobacter nicotianae provides the H2 O2 necessary via reductive activation of ambient oxygen. The reactions are performed in choline chloride-based deep eutectic solvents serving as co-solvent and stoichiometric reductant at the same time. Very promising product concentrations (up to 15 mM enantiopure sulfoxide) and catalyst performances (turnover numbers of 150,000 and 2100 for the peroxygenase and oxidase, respectively) have been achieved.

Keywords: biocatalysis; enantioselectivity; natural deep eutectic solvents; peroxygenases; sulfoxidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agrocybe / chemistry
  • Agrocybe / enzymology*
  • Alcohol Oxidoreductases / metabolism*
  • Biocatalysis
  • Biological Products / chemistry*
  • Choline / chemistry
  • Hydrogen / chemistry
  • Hydrogen Peroxide / chemistry
  • Micrococcaceae / chemistry
  • Micrococcaceae / enzymology*
  • Mixed Function Oxygenases / metabolism*
  • Oxidation-Reduction
  • Oxygen / chemistry
  • Photochemical Processes
  • Safrole / analogs & derivatives*
  • Safrole / chemistry
  • Solvents / chemistry
  • Stereoisomerism
  • Sulfides / chemistry*

Substances

  • Biological Products
  • Solvents
  • Sulfides
  • Hydrogen
  • methylphenylsulfide
  • Hydrogen Peroxide
  • Mixed Function Oxygenases
  • Alcohol Oxidoreductases
  • choline oxidase
  • peroxygenase
  • Choline
  • Safrole
  • Oxygen
  • sulfoxide

Supplementary concepts

  • Agrocybe aegerita
  • Glutamicibacter nicotianae