ArticleJournal of the American Chemical Society2018
Total Enzyme Syntheses of Napyradiomycins A1 and B1.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed.
- MALDI Tandem Mass Spectrometry for Colony-Based Dereplication of Natural Products.bioRxiv : the preprint server for biology · 2026Article
- Chemoenzymatic Diazo Synthesis Enabled by Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases.Journal of the American Chemical Society · 2026Article
- In Vitro Characterization of the Aromatic SAM-Dependent C-Methyltransferase NapB5.Journal of natural products · 2025Article
- Separation of halide oxidation and substrate halogenation chemistries rationalizes site-selective vanadium dependent haloperoxidase catalysis.bioRxiv : the preprint server for biology · 2025Article
- Machine learning-led semi-automated medium optimization reveals salt as key for flaviolin production in Pseudomonas putida.Communications biology · 2025Article
- Intermolecular 1,2,4-Thiadiazole Synthesis Enabled by Enzymatic Halide Recycling with Vanadium-Dependent Haloperoxidases.Journal of the American Chemical Society · 2025Article
- Insights for napyradiomycin family: structures, bioactivities and biosynthetic pathways.Archives of microbiology · 2025Review
- Unraveling the molecular basis of substrate specificity and halogen activation in vanadium-dependent haloperoxidases.Nature communications · 2025Article
- In Silico Screening ofBiologics : targets & therapy · 2025Article
- Vanadium-dependent haloperoxidases from diverse microbes halogenate exogenous alkyl quinolone quorum sensing signals.bioRxiv : the preprint server for biology · 2024Article
- Regioselective Halogenation of Lavanducyanin by a Site-Selective Vanadium-Dependent Chloroperoxidase.Organic letters · 2024Article
- Review
- Vanadium haloperoxidases as noncanonical terpene synthases.Methods in enzymology · 2024Article
- Ru(phen)ChemistryOpen · 2023Article
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Endowing homodimeric carbamoyltransferase GdmN with iterative functions through structural characterization and mechanistic studies.Nature communications · 2022Article
- Structural Basis of Stereospecific Vanadium-Dependent Haloperoxidase Family Enzymes in Napyradiomycin Biosynthesis.Biochemistry · 2022Article
- Halogenation in Fungi: What Do We Know and What Remains to Be Discovered?Molecules (Basel, Switzerland) · 2022Review
- A Diazo-Hooker Reaction, Inspired by the Biosynthesis of Azamerone.Organic letters · 2022Article
- Halogenases: a palette of emerging opportunities for synthetic biology-synthetic chemistry and C-H functionalisation.Chemical Society reviews · 2021Review
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8 authors.
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Abstract
The biosynthetic route to the napyradiomycin family of bacterial meroterpenoids has been fully described 32 years following their original isolation and 11 years after their gene cluster discovery. The antimicrobial and cytotoxic natural products napyradiomycins A1 and B1 are produced using three organic substrates (1,3,6,8-tetrahydroxynaphthalene, dimethylallyl pyrophosphate, and geranyl pyrophosphate), and catalysis via five enzymes: two aromatic prenyltransferases (NapT8 and T9); and three vanadium dependent haloperoxidase (VHPO) homologues (NapH1, H3, and H4). Building upon the previous characterization of NapH1, H3, and T8, we herein describe the initial (NapT9, H1) and final (NapH4) steps required for napyradiomycin construction. This remarkably streamlined biosynthesis highlights the utility of VHPO enzymology in complex natural product generation, as NapH4 efficiently performs a unique chloronium-induced terpenoid cyclization to establish two stereocenters and a new carbon-carbon bond, and dual-acting NapH1 catalyzes chlorination and etherification reactions at two distinct stages of the pathway. Moreover, we employed recombinant napyradiomycin biosynthetic enzymes to chemoenzymatically synthesize milligram quantities in one pot in 1 day. This method represents a viable enantioselective approach to produce complex halogenated metabolites, like napyradiomycin B1, that have yet to be chemically synthesized.
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