ArticleJournal of the American Chemical Society2015
Tandem prenyltransferases catalyze isoprenoid elongation and complexity generation in biosynthesis of quinolone alkaloids.
Article in Journal of the American Chemical Society, 2015. 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, 68 citations in OpenAlex.
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- Two types of coumarins-specific enzymes complete the last missing steps in pyran- and furanocoumarins biosynthesis.Acta pharmaceutica Sinica. B · 2024Article
- Genome mining and biosynthetic pathways of marine-derived fungal bioactive natural products.Frontiers in microbiology · 2024Review
- Regioselective Biocatalytic C4-Prenylation of Unprotected Tryptophan Derivatives.Chembiochem : a European journal of chemical biology · 2022Article
- Scalable total synthesis of (+)-aniduquinolone A and its acid-catalyzed rearrangement to aflaquinolones.Communications chemistry · 2022Article
- Synthetic and biosynthetic methods for selective cyclisations of 4,5-epoxy alcohols to tetrahydropyrans.Organic & biomolecular chemistry · 2022Review
- Berberine bridge enzyme-like oxidase-catalysed double bond isomerization acts as the pathway switch in cytochalasin synthesis.Nature communications · 2022Article
- FAD-dependent enzyme-catalysed intermolecular [4+2] cycloaddition in natural product biosynthesis.Nature chemistry · 2020Article
- Alkaloids from Marine Fungi: Promising Antimicrobials.Antibiotics (Basel, Switzerland) · 2020Review
- Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases.Natural product reports · 2020Review
- Immunosuppressant mycophenolic acid biosynthesis employs a new globin-like enzyme for prenyl side chain cleavage.Acta pharmaceutica Sinica. B · 2019Article
- Identification of the Pyranonigrin A Biosynthetic Gene Cluster by Genome Mining inAIChE journal. American Institute of Chemical Engineers · 2018Article
- Prenyl Praxis: A Method for Direct Photocatalytic Defluoroprenylation.Journal of the American Chemical Society · 2018Article
- Enzymatic one-step ring contraction for quinolone biosynthesis.Nature communications · 2018Article
- Oxidative Cyclization in Natural Product Biosynthesis.Chemical reviews · 2017Review
- Enzyme-catalyzed cationic epoxide rearrangements in quinolone alkaloid biosynthesis.Nature chemical biology · 2017Article
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Authors and funding
7 authors at 3 institutions in 2 countries.
Funding
Abstract
Modification of natural products with prenyl groups and the ensuing oxidative transformations are important for introducing structural complexity and biological activities. Penigequinolones (1) are potent insecticidal alkaloids that contain a highly modified 10-carbon prenyl group. Here we reveal an iterative prenylation mechanism for installing the 10-carbon unit using two aromatic prenyltransferases (PenI and PenG) present in the gene cluster of 1 from Penicillium thymicola. The initial Friedel-Crafts alkylation is catalyzed by PenI to yield dimethylallyl quinolone 6. The five-carbon side chain is then dehydrogenated by a flavin-dependent monooxygenase to give aryl diene 9, which serves as the electron-rich substrate for a second alkylation with dimethylallyl diphosphate to yield stryrenyl product 10. The completed, oxidized 10-carbon prenyl group then undergoes further structural morphing to yield yaequinolone C (12), the immediate precursor of 1. Our studies have therefore uncovered an unprecedented prenyl chain extension mechanism in natural product biosynthesis.
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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.