ArticleNature communications2020
Oxepinamide F biosynthesis involves enzymatic D-aminoacyl epimerization, 3H-oxepin formation, and hydroxylation induced double bond migration.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed, 28 citations in OpenAlex.
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- A FungalJournal of agricultural and food chemistry · 2026Article
- Expression of a strain-specific non-ribosomal peptide synthetase from Aspergillus lentulus lead to the discovery of a new fungal alkaloid lentoquinazoline.The Journal of antibiotics · 2026Article
- Integrated Metabolomic and Genomic Insights into Amino Acid Incorporation Within the Hybrid Polyketide-Alkaloid Antibiotic TLN-05220.ACS chemical biology · 2026Article
- Integrated metabolomic and genomic insights into amino acid incorporation within the hybrid polyketide-alkaloid antibiotic TLN-05220.bioRxiv : the preprint server for biology · 2025Article
- Biosynthesis of Circumdatins Employs an Anthranilate Tailoring Pathway for NRPS Substrate Supplies.Organic letters · 2025Article
- Reimagining Dearomatization: Arenophile-Mediated Single-Atom Insertions and π-Extensions.Accounts of chemical research · 2025Article
- Expression of a Colletotrichum polyketide synthase gene in Aspergillus nidulans leads to unexpected conjugates with a host metabolite.Archives of microbiology · 2025Article
- A basidomycetous hydroxynaphthalene-prenylating enzyme exhibits promiscuity toward prenyl donors.Applied microbiology and biotechnology · 2023Article
- Diketopiperazine Alkaloids and Bisabolene Sesquiterpenoids fromMarine drugs · 2023Article
- Application of Gene Knockout and Heterologous Expression Strategy in Fungal Secondary Metabolites Biosynthesis.Marine drugs · 2022Review
- A terpene cyclase fromRSC advances · 2022Article
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Authors and funding
4 authors at 2 institutions in 2 countries.
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No grant is acknowledged in the PubMed record.
Abstract
Oxepinamides are derivatives of anthranilyl-containing tripeptides and share an oxepin ring and a fused pyrimidinone moiety. To the best of our knowledge, no studies have been reported on the elucidation of an oxepinamide biosynthetic pathway and conversion of a quinazolinone to a pyrimidinone-fused 1H-oxepin framework by a cytochrome P450 enzyme in fungal natural product biosynthesis. Here we report the isolation of oxepinamide F from Aspergillus ustus and identification of its biosynthetic pathway by gene deletion, heterologous expression, feeding experiments, and enzyme assays. The nonribosomal peptide synthase (NRPS) OpaA assembles the quinazolinone core with D-Phe incorporation. The cytochrome P450 enzyme OpaB catalyzes alone the oxepin ring formation. The flavoenzyme OpaC installs subsequently one hydroxyl group at the oxepin ring, accompanied by double bond migration. The epimerase OpaE changes the D-Phe residue back to L-form, which is essential for the final methylation by OpaF.
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