ArticleAngewandte Chemie (International ed. in English)2018
Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products.
Article in Angewandte Chemie (International ed. in English), 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed, 55 citations in OpenAlex.
- Chlorination of Amines by a Vanadium-Dependent Chloroperoxidase.ACS catalysis · 2026Article
- Oxidative Rearrangement of Indoles Enabled by Promiscuous Cryptic Halogenation with Vanadium-Dependent Haloperoxidases.ACS catalysis · 2026Article
- Insights for napyradiomycin family: structures, bioactivities and biosynthetic pathways.Archives of microbiology · 2025Review
- Vanadium-dependent haloperoxidases from diverse microbes halogenate exogenous alkyl quinolone quorum sensing signals.bioRxiv : the preprint server for biology · 2024Article
- MAR4Journal of natural products · 2024Review
- 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
- Bioinspired Total Synthesis of Pyritide A2 through Pyridine Ring Synthesis.Angewandte Chemie (International ed. in English) · 2022Article
- Structural Basis of Stereospecific Vanadium-Dependent Haloperoxidase Family Enzymes in Napyradiomycin Biosynthesis.Biochemistry · 2022Article
- Biosynthesis of Largimycins inACS chemical biology · 2022Article
- Synthesis of (±)-Setigerumine I: Biosynthetic Origins of the Elusive Racemic Papaveraceae Isoxazolidine Alkaloids*.Angewandte Chemie (International ed. in English) · 2021Article
- Cryptic halogenation reactions in natural product biosynthesis.Natural product reports · 2021Review
- Investigating the Role of Vanadium-Dependent Haloperoxidase Enzymology in Microbial Secondary Metabolism and Chemical Ecology.mSystems · 2021Article
- Microbial soluble aromatic prenyltransferases for engineered biosynthesis.Synthetic and systems biotechnology · 2021Article
- Bacterial terpenome.Natural product reports · 2021Review
- Meroterpenoid natural products from Streptomyces bacteria - the evolution of chemoenzymatic syntheses.Natural product reports · 2020Review
- Acceptor substrate determines donor specificity of an aromatic prenyltransferase: expanding the biocatalytic potential of NphB.Applied microbiology and biotechnology · 2020Article
- Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases.Natural product reports · 2020Review
- Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion.Journal of the American Chemical Society · 2019Article
- Total Enzyme Syntheses of Napyradiomycins A1 and B1.Journal of the American Chemical Society · 2018Article
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Authors and funding
9 authors at 2 institutions in 2 countries.
Funding
Abstract
The naphterpins and marinones are naphthoquinone meroterpenoids with an unusual aromatic oxidation pattern that is biosynthesized from 1,3,6,8-tetrahydroxynaphthalene (THN). We propose that cryptic halogenation of THN derivatives by vanadium-dependent chloroperoxidase (VCPO) enzymes is key to this biosynthetic pathway, despite the absence of chlorine in these natural products. This speculation inspired a total synthesis to mimic the naphterpin/marinone biosynthetic pathway. In validation of this biogenetic hypothesis, two VCPOs were discovered that interconvert several of the proposed biosynthetic intermediates.
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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 OpenQuestion graph.