ArticleNature communications2023
A flavin-monooxygenase catalyzing oxepinone formation and the complete biosynthesis of vibralactone.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 15 citations in OpenAlex.
- Dual cytosine modification through hydroxylation and arabinofuranosylation in phages.Nature chemical biology · 2026Article
- Mimicking Extradiol Dioxygenase Reactivity on Iridium.Journal of the American Chemical Society · 2026Article
- Genome mining reveals the unique function of UbiA-type prenyltransferase in Laetiporus sulphureus.Natural products and bioprospecting · 2026Article
- Vibralactone derivatives isolated from co-cultures of the basidiomycetes Stereum hirsutum and Boreostereum vibrans.Natural products and bioprospecting · 2025Article
- Synthetic study toward vibralactone.Beilstein journal of organic chemistry · 2025Article
- Proteomics: An Essential Tool to Study Plant-Specialized Metabolism.Biomolecules · 2024Review
- Baeyer-Villiger oxidation: a promising tool for the synthesis of natural products: a review.RSC advances · 2024Review
- The shikimate pathway: gateway to metabolic diversity.Natural product reports · 2024Review
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Authors and funding
7 authors at 3 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
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 β-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.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the Socratic graph.