A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone
文献类型：期刊论文
| 作者 | Feng,Ke-Na; Zhang,Yue ; Zhang,Mingfang; Yang,Yan-Long; Liu,Ji-Kai; Pan,Lifeng; Zeng,Ying
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| 刊名 | NATURE COMMUNICATIONS
 |
| 出版日期 | 2023 |
| 卷号 | 14期号:1页码:3436 |
| 关键词 | ENZYMATIC TOTAL-SYNTHESIS PHENOL HYDROXYLASE PANCREATIC LIPASE CRYSTAL-STRUCTURE INHIBITOR LACTONE FERMENTATIONS GILVOCARCIN METABOLITES |
| ISSN号 | 2041-1723 |
| DOI | 10.1038/s41467-023-39108-x |
| 英文摘要 | Vibralactone is a strong lipase inhibitor and a bicyclic beta-lactone containing an oxepinone ring, whose biosynthetic construction was unknown. Here the authors identify an oxepinone-building flavin monooxygenase VibO that is involved in the biosynthesis of vibralactone, and determine its X-ray crystal structure. Oxepinone rings represent one of structurally unusual motifs of natural products and the biosynthesis of oxepinones is not fully understood. 1,5-Seco-vibralactone (3) features an oxepinone motif and is a stable metabolite isolated from mycelial cultures of the mushroom Boreostereum vibrans. Cyclization of 3 forms vibralactone (1) whose beta-lactone-fused bicyclic core originates from 4-hydroxybenzoate, yet it remains elusive how 4-hydroxybenzoate is converted to 3 especially for the oxepinone ring construction in the biosynthesis of 1. In this work, using activity-guided fractionation together with proteomic analyses, we identify an NADPH/FAD-dependent monooxygenase VibO as the key enzyme performing a crucial ring-expansive oxygenation on the phenol ring to generate the oxepin-2-one structure of 3. The crystal structure of VibO reveals that it forms a dimeric phenol hydroxylase-like architecture featured with a unique substrate-binding pocket adjacent to the bound FAD. Computational modeling and solution studies provide insight into the likely VibO active site geometry, and suggest possible involvement of a flavin-C4a-OO(H) intermediate. |
| 学科主题 | Science & Technology - Other Topics |
| WOS记录号 | WOS:001003866300026 |
| 源URL | [http://ir.kib.ac.cn/handle/151853/74867]  |
| 专题 | 中国科学院昆明植物研究所 |
| 推荐引用方式 GB/T 7714 | Feng,Ke-Na,Zhang,Yue,Zhang,Mingfang,et al. A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone[J]. NATURE COMMUNICATIONS,2023,14(1):3436. |
| APA | Feng,Ke-Na.,Zhang,Yue.,Zhang,Mingfang.,Yang,Yan-Long.,Liu,Ji-Kai.,...&Zeng,Ying.(2023).A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone.NATURE COMMUNICATIONS,14(1),3436. |
| MLA | Feng,Ke-Na,et al."A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone".NATURE COMMUNICATIONS 14.1(2023):3436. |
入库方式： OAI收割
来源：昆明植物研究所
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