ArticleNature chemistry2017
A unifying paradigm for naphthoquinone-based meroterpenoid (bio)synthesis.
Article in Nature chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 32 papers.
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Who cites it
32 citing papers in PubMed, 85 citations in OpenAlex.
- MALDI Tandem Mass Spectrometry for Colony-Based Dereplication of Natural Products.bioRxiv : the preprint server for biology · 2026Article
- Overriding the radical polarity matching principle: selective chlorohydroxylation of electron-deficient alkenes enabled by Ce photocatalysis.Chemical science · 2026Article
- In Vitro Characterization of the Aromatic SAM-Dependent C-Methyltransferase NapB5.Journal of natural products · 2025Article
- Insights for napyradiomycin family: structures, bioactivities and biosynthetic pathways.Archives of microbiology · 2025Review
- Halogenase-Assisted Biocatalytic Derivatization of Aminothiazoles and Cephalosporin Antibiotics.The Journal of organic chemistry · 2025Article
- Unraveling the molecular basis of substrate specificity and halogen activation in vanadium-dependent haloperoxidases.Nature communications · 2025Article
- Chemoenzymatic C,C-Bond Forming Cascades by Cryptic Vanadium Haloperoxidase Catalyzed Bromination.Organic letters · 2025Article
- Regioselective Halogenation of Lavanducyanin by a Site-Selective Vanadium-Dependent Chloroperoxidase.Organic letters · 2024Article
- Vanadium haloperoxidases as noncanonical terpene synthases.Methods in enzymology · 2024Article
- Charting the Evolution of Chemoenzymatic Strategies in the Syntheses of Complex Natural Products.Journal of the American Chemical Society · 2023Review
- Natural Products from Singapore Soil-DerivedMolecules (Basel, Switzerland) · 2023Article
- Structural Basis of Stereospecific Vanadium-Dependent Haloperoxidase Family Enzymes in Napyradiomycin Biosynthesis.Biochemistry · 2022Article
- A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone.Organic letters · 2022Article
- Biological activities of meroterpenoids isolated from different sources.Frontiers in pharmacology · 2022Review
- Antibacterial Meroterpenoids, Merochlorins G-J from the Marine BacteriumMarine drugs · 2021Article
- Cryptic halogenation reactions in natural product biosynthesis.Natural product reports · 2021Review
- Halogenases: a palette of emerging opportunities for synthetic biology-synthetic chemistry and C-H functionalisation.Chemical Society reviews · 2021Review
- Recent trends in biocatalysis.Chemical Society reviews · 2021Review
- Microbial soluble aromatic prenyltransferases for engineered biosynthesis.Synthetic and systems biotechnology · 2021Article
- Bacterial terpenome.Natural product reports · 2021Review
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 2 countries.
Funding
Abstract
Bacterial meroterpenoids constitute an important class of natural products with diverse biological properties and therapeutic potential. The biosynthetic logic for their production is unknown and defies explanation via classical biochemical paradigms. A large subgroup of naphthoquinone-based meroterpenoids exhibits a substitution pattern of the polyketide-derived aromatic core that seemingly contradicts the established reactivity pattern of polyketide phenol nucleophiles and terpene diphosphate electrophiles. We report the discovery of a hitherto unprecedented enzyme-promoted α-hydroxyketone rearrangement catalysed by vanadium-dependent haloperoxidases to account for these discrepancies in the merochlorin and napyradiomycin class of meroterpenoid antibiotics, and we demonstrate that the α-hydroxyketone rearrangement is potentially a conserved biosynthetic reaction in this molecular class. The biosynthetic α-hydroxyketone rearrangement was applied in a concise total synthesis of naphthomevalin, a prominent member of the napyradiomycin meroterpenes, and sheds further light on the mechanism of this unifying enzymatic transformation.
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Registered trials
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 OpenQuestion graph.