ArticleJournal of the American Chemical Society2016
OxaD: A Versatile Indolic Nitrone Synthase from the Marine-Derived Fungus Penicillium oxalicum F30.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Investigating Opioid Receptor Activity through Biocatalytic Halogenation and Oxidation of Mitragynine.ACS chemical biology · 2026Article
- Biosynthesis of the 5-Isoxazolidinone-Containing Hexacyclic Structure of Parnafungin.Journal of the American Chemical Society · 2025Article
- Advanced Technologies for Large Scale Supply of Marine Drugs.Marine drugs · 2025Review
- Mechanism of Nitrone Formation by a Flavin-Dependent Monooxygenase.Biochemistry · 2024Article
- Improvement of Targeted Fungi Secondary Metabolite Production Using a Systematic Experimental Design and Chemometrics Analysis.Methods and protocols · 2023Article
- Molecular Dynamics Simulations Guide Chimeragenesis and Engineered Control of Chemoselectivity in Diketopiperazine Dimerases.Angewandte Chemie (International ed. in English) · 2023Article
- Recent Advances in the Synthesis of Marine-Derived Alkaloids via Enzymatic Reactions.Marine drugs · 2022Review
- Biosynthesis of Terpenoid-Pyrrolobenzoxazine Hybrid Natural Product CJ-12662.Angewandte Chemie (International ed. in English) · 2022Article
- Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with HThe Journal of organic chemistry · 2021Article
- A Homeodomain-Containing Transcriptional FactorFrontiers in microbiology · 2021Article
- Bifunctional Nitrone-Conjugated Secondary Metabolite Targeting the Ribosome.Journal of the American Chemical Society · 2020Article
- Flavin-Dependent Monooxygenases NotI and NotI' Mediate Spiro-Oxindole Formation in Biosynthesis of the Notoamides.Chembiochem : a European journal of chemical biology · 2020Article
- Applications of Marine-Derived Microorganisms and Their Enzymes in Biocatalysis and Biotransformation, the Underexplored Potentials.Frontiers in microbiology · 2019Review
- Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosynthetic pathway.Organic & biomolecular chemistry · 2018Article
- Structural and stereochemical diversity in prenylated indole alkaloids containing the bicyclo[2.2.2]diazaoctane ring system from marine and terrestrial fungi.Natural product reports · 2018Review
- Bioinspired chemical synthesis of monomeric and dimeric stephacidin A congeners.Nature chemistry · 2018Article
- Characterization of the flavoenzyme XiaK as anChemical science · 2017Article
- Heteroatom-Heteroatom Bond Formation in Natural Product Biosynthesis.Chemical reviews · 2017Review
- Joining Forces: Fermentation and Organic Synthesis for the Production of Complex Heterocycles.The Journal of organic chemistry · 2016Review
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10 authors.
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Abstract
Indole alkaloids are a diverse class of natural products known for their wide range of biological activities and complex chemical structures. Rarely observed in this class are indolic nitrones, such as avrainvillamide and waikialoid, which possess potent bioactivities. Herein the oxa gene cluster from the marine-derived fungus Penicillium oxalicum F30 is described along with the characterization of OxaD, a flavin-dependent oxidase that generates roquefortine L, a nitrone-bearing intermediate in the biosynthesis of oxaline. Nitrone functionality in roquefortine L was confirmed by spectroscopic methods and 1,3-dipolar cycloaddition with methyl acrylate. OxaD is a versatile biocatalyst that converts an array of semisynthetic roquefortine C derivatives bearing indoline systems to their respective nitrones. This work describes the first implementation of a nitrone synthase as a biocatalyst and establishes a novel platform for late-stage diversification of a range of complex natural products.
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