Asymmetric synthesis of sulfoxides by novel Baeyer-Villiger monooxygenase from Fusarium

• Published in: Tetrahedron Vol. 131; pp. 133204 - 133210
• Main Authors: Le Viet, Lan Huong, Nemoto, Hiroumi, Tamura, Mayumi, Matsuda, Tomoko
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 26.01.2023; Elsevier
• Subjects: Aqueous-organic media; Asymmetric sulfoxidation; Chemistry; Chemistry, Organic; Chiral compound; Monooxygenase; Physical Sciences; Science & Technology; Whole cell reaction; Whole cell reaction; Chiral compound; Aqueous-organic media; Asymmetric sulfoxidation; Monooxygenase; SELECTIVE OXIDATION; BIOCATALYTIC PROPERTIES; SULFIDES; PHENYLACETONE-MONOOXYGENASE
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2022.133204

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 (FBVMO), was investigated. The effect of organic cosolvents was also examined using purified FBVMO, improving the activity by up to 247%. E. coli whole cell expressing FBVMO 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). [Display omitted] •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).