Sustainable approach for highly-enantioselective synthesis of lactones by a Baeyer-Villiger monooxygenase from Fusarium

Baeyer-Villiger monooxygenases (BVMOs), flavin-dependent enzymes that use atmospheric oxygen to catalyze oxidation reactions, are valuable for various applications. In this study, we employed a novel BVMO from the fungus, Fusarium sp. NBRC 109816, (FBVMO) to synthesize diverse chiral lactones. The e...

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Veröffentlicht in:Tetrahedron 2024-03, Vol.154, p.133875, Article 133875
Hauptverfasser: Le Viet, Lan Huong, Tamura, Mayumi, Matsuda, Tomoko
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Sprache:eng
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Zusammenfassung:Baeyer-Villiger monooxygenases (BVMOs), flavin-dependent enzymes that use atmospheric oxygen to catalyze oxidation reactions, are valuable for various applications. In this study, we employed a novel BVMO from the fungus, Fusarium sp. NBRC 109816, (FBVMO) to synthesize diverse chiral lactones. The enzyme demonstrated a broad substrate compatibility with a variety of cyclic ketones. In addition, the preparative-scale reactions were successfully conducted, and the chiral lactones were obtained with yields of up to 91 % and enantiomeric excess (ee) values of up to 99 % (S). [Display omitted] •A green asymmetric synthetic method of chiral lactones 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.•Chiral lactones were obtained in up to 91 % isolated yield and up to ee 99 %(S).
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2024.133875