Asymmetric synthesis of sulfoxides by novel Baeyer-Villiger monooxygenase from Fusarium. (26th January 2023)

• Record Type: Journal Article
• Authors: Le Viet, Lan Huong; Nemoto, Hiroumi; Tamura, Mayumi; Matsuda, Tomoko
• Is Part Of: Tetrahedron. Volume 131(2023)
• Publication Date: 2023-01-26
• Subjects: Asymmetric sulfoxidation -- Whole cell reaction -- Monooxygenase -- Chiral compound -- Aqueous-organic media; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2022.133204
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: In the chemical industry, the oxidation reaction is one of the essential reactions, although some oxidizing reagents are potentially explosive. Hence, the safe reaction catalyzed by monooxygenases, enzymes that can catalyze oxidation reactions using molecular oxygen in the air, becomes an attractive alternative as it promotes green and sustainable chemistry. Herein, sulfoxidation of alkyl aryl sulfides by a novel Baeyer-Villiger monooxygenase from a fungus, Fusarium sp. NBRC 109816 ( F BVMO), was investigated. The effect of organic cosolvents was also examined using purified F BVMO, improving the activity by up to 247%. E. coli whole cell expressing F BVMO was used for the synthetic purpose, and various chiral sulfoxides were obtained successfully in up to 92% isolated yield and up to 99% ee ( R ). Graphical abstract: Image 1 Highlights: An asymmetric oxidation reaction of various sulfides was developed. A Baeyer-Villiger monooxygenase from Fusarium sp. was used as a catalyst. The reaction does not need explosive reagents; the oxidant is oxygen in the air. Adding an organic cosolvent improved the enzyme activity to up to 247%. Chiral sulfoxides were obtained in up to 92% isolated yield and up to ee 99%( R ).