ArticleJournal of the American Chemical Society2016
P450-Mediated Coupling of Indole Fragments To Forge Communesin and Unnatural Isomers.
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 22 papers.
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Who cites it
22 citing papers in PubMed, 66 citations in OpenAlex.
- Review
- Biosynthesis of the 5-Isoxazolidinone-Containing Hexacyclic Structure of Parnafungin.Journal of the American Chemical Society · 2025Article
- Mechanistic Perspective on C-N and C-S Bond Construction Catalyzed by Cytochrome P450 Enzymes.ACS bio & med chem Au · 2025Review
- Enantioselective Cobaltaphotoredox-Catalyzed C-H Activation.Journal of the American Chemical Society · 2024Article
- Exploring the Diverse Landscape of Fungal Cytochrome P450-Catalyzed Regio- and Stereoselective Dimerization of Diketopiperazines.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Article
- Enzymatic Benzofuranoindoline Formation in the Biosynthesis of the Strained Bridgehead Bicyclic Dipeptide (+)-Azonazine A.Angewandte Chemie (International ed. in English) · 2023Article
- Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers.Natural product reports · 2023Review
- Brønsted acid-catalyzed asymmetric dearomatization for synthesis of chiral fused polycyclic enone and indoline scaffolds.Science advances · 2023Article
- The Transformative Power of Biocatalysis in Convergent Synthesis.Journal of the American Chemical Society · 2022Review
- Branching and converging pathways in fungal natural product biosynthesis.Fungal biology and biotechnology · 2022Review
- Computational-Based Mechanistic Study and Engineering of Cytochrome P450 MycG for Selective Oxidation of 16-Membered Macrolide Antibiotics.Journal of the American Chemical Society · 2020Article
- Discovery and Total Synthesis of a Bis(cyclotryptamine) Alkaloid Bearing the Elusive Piperidinoindoline Scaffold.Journal of the American Chemical Society · 2020Article
- Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.Organic letters · 2020Article
- Molecular basis for the P450-catalyzed C-N bond formation in indolactam biosynthesis.Nature chemical biology · 2019Article
- Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.Journal of the American Chemical Society · 2019Article
- Enzymatic Cascade Reactions in Biosynthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Detecting and prioritizing biosynthetic gene clusters for bioactive compounds in bacteria and fungi.Applied microbiology and biotechnology · 2019Review
- Efficient biosynthesis of heterodimeric CNature communications · 2018Article
- Biosynthesis of Heptacyclic Duclauxins Requires Extensive Redox Modifications of the Phenalenone Aromatic Polyketide.Journal of the American Chemical Society · 2018Article
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
Dimeric indole alkaloids are structurally diverse natural products that have attracted significant attention from the synthetic and biosynthetic communities. Here, we describe the characterization of a P450 monooxygenase CnsC from Penicillium that catalyzes the heterodimeric coupling between two different indole moieties, tryptamine and aurantioclavine, to construct vicinal quaternary stereocenters and yield the heptacyclic communesin scaffold. We show, via biochemical characterization, substrate analogues, and computational methods that CnsC catalyzes the C3-C3' carbon-carbon bond formation and controls the regioselectivities of the pair of subsequent aminal bond formations to yield the communesin core. Use of ω-N-methyltryptamine and tryptophol in place of tryptamine led to the enzymatic synthesis of isocommunesin compounds, which have not been isolated to date.
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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.