Expanding the toolbox of Baeyer-Villiger and flavin monooxygenase biocatalysts for the enantiodivergent green synthesis of sulfoxides

Jingyue Wu; Silvia Anselmi; Alexandra T P Carvalho; Jill Caswell; Derek J Quinn; Thomas S Moody; Daniele Castagnolo

doi:10.1039/d4gc02657h

Expanding the toolbox of Baeyer-Villiger and flavin monooxygenase biocatalysts for the enantiodivergent green synthesis of sulfoxides

Green Chem. 2024 Jul 5;26(15):8685-8693. doi: 10.1039/d4gc02657h. eCollection 2024 Jul 29.

Authors

Jingyue Wu¹, Silvia Anselmi¹, Alexandra T P Carvalho², Jill Caswell², Derek J Quinn², Thomas S Moody^{2

3}, Daniele Castagnolo¹

Affiliations

¹ Department of Chemistry, University College London 20 Gordon Street WC1H 0AJ London UK d.castagnolo@ucl.ac.uk.
² Department of Biocatalysis & Isotope Chemistry Almac 20 Seagoe Industrial Estate Craigavon BT63 5QD UK tom.moody@almacgroup.com.
³ Arran Chemical Company Limited, Unit 1 Monksland Industrial Estate Athlone Co. Roscommon Ireland.

Abstract

Two new monooxygenase biocatalysts, the Baeyer-Villiger monooxygenase BVMO145 and the flavin monooxygenase FMO401 from Almac library, have been found to catalyse the enantiodivergent oxidation of sulfides bearing N-heterocyclic substituents into sulfoxides under mild and green conditions. The biocatalyst BVMO145 provides (S)-sulfoxides while the flavin monooxygenase FMO401 affords (R)-sulfoxides with good conversions and high ee.