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- Title
Elucidation of a Dearomatization Route in the Biosynthesis of Oxysporidinone Involving a TenA‐like Cytochrome P450 Enzyme.
- Authors
Li, Dan; Wang, Wenxuan; Xu, Kangping; Li, Jing; Long, Bi; Li, Zhansheng; Tan, Guishan; Yu, Xia
- Abstract
Oxidative dearomatization of phenols is an important transformation for synthesis of complex molecules. Oxysporidinone and related 2‐pyridones feature a hydroxy‐substituted cyclohexanone ring, which has been proposed to form by phenol dearomatization, although the details of the biochemical process are still unknown. In this study, we identified the oxysporidinone biosynthetic gene cluster in Fusarium oxysporum by regulator activation and gene knockout studies. Through in vivo and in vitro studies, we confirmed that the phenol dearomatization process involves two enzymes. OsdM, a TenA‐like cytochrome P450 with expected ring‐expansion activity, converts the phenol ring and the 4‐hydroxy‐2‐pyridone core into an unexpected fused [6‐5‐6] ring system. OsdN, on the other hand, catalyzes two successive ene reduction reactions, followed by hydroxylation by OsdM. This new route enriches current knowledge on enzymatic phenol dearomatization and the mechanism of TenA‐like P450s.
- Subjects
CYTOCHROME P-450; BIOSYNTHESIS; ENE reactions; GENETIC regulation; GENE knockout
- Publication
Angewandte Chemie, 2023, Vol 135, Issue 25, p1
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.202301976