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...
Gespeichert in:
Veröffentlicht in: | Tetrahedron 2024-03, Vol.154, p.133875, Article 133875 |
---|---|
Hauptverfasser: | , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
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 |