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

Yongru Li, Yunjian Ma, Peilin Li, Xizhen Zhang, Doris Ribitsch, Miguel Alcalde, Frank Hollmann, Yonghua Wang

2020ChemPlusChem29 citationsDOIOpen Access PDF

Abstract

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 H 2 O 2 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.

Topics & Concepts

ThioanisoleChemistryEnantioselective synthesisCholine chlorideSulfoxideCholine oxidaseBiocatalysisThioetherOrganic chemistryCatalysisCombinatorial chemistryIonic liquidEnzymeAcetylcholinesteraseChemical Synthesis and ReactionsOxidative Organic Chemistry ReactionsEnzyme Catalysis and Immobilization
Enantioselective Sulfoxidation of Thioanisole by Cascading a Choline Oxidase and a Peroxygenase in the Presence of Natural Deep Eutectic Solvents | Litcius