ArticleAngewandte Chemie (International ed. in English)2015
Elucidation of the concise biosynthetic pathway of the communesin indole alkaloids.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 30 papers.
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Who cites it
30 citing papers in PubMed, 114 citations in OpenAlex.
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- Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers.Natural product reports · 2023Review
- Biosynthesis of pleuromutilin congeners using anChemical science · 2023Article
- Derivation of the multiply-branched ergot alkaloid pathway of fungi.Microbial biotechnology · 2023Review
- Genome Mining Discovery of a New Benzazepine Alkaloid Pseudofisnin A from the Marine FungusAntibiotics (Basel, Switzerland) · 2022Article
- Design, Synthesis, and Bioactivity Study of Novel Tryptophan Derivatives Containing Azepine and Acylhydrazone Moieties.Molecules (Basel, Switzerland) · 2022Article
- Branching and converging pathways in fungal natural product biosynthesis.Fungal biology and biotechnology · 2022Review
- Antibiotic Biosynthesis Pathways from EndophyticAntibiotics (Basel, Switzerland) · 2021Article
- Molecular insights into the endoperoxide formation by Fe(II)/α-KG-dependent oxygenase NvfI.Nature communications · 2021Article
- Biosynthesis and synthetic biology of psychoactive natural products.Chemical Society reviews · 2021Review
- Regulation of Secondary Metabolism in theInternational journal of molecular sciences · 2020Review
- TheInternational journal of molecular sciences · 2020Article
- Enzyme-Catalyzed Azepinoindole Formation in Clavine Alkaloid Biosynthesis.Organic letters · 2020Article
- Brocaeloid D, a novel compound isolated from a wheat pathogenic fungus,Synthetic and systems biotechnology · 2019Article
- Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.Journal of the American Chemical Society · 2019Article
- Synthesis of the ABCDG ring skeleton of communesin F based on carboborylation of 1,3-diene and Bi(OTf)The Journal of antibiotics · 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
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
The communesins are a prominent class of indole alkaloids isolated from Penicillium species. Owing to their daunting structural framework and potential as pharmaceuticals, communesins have inspired numerous synthetic studies. However, the genetic and biochemical basis of communesin biosynthesis has remained unexplored. Herein, we report the identification and characterization of the communesin (cns) biosynthetic gene cluster from Penicillium expansum. We confirmed that communesin is biosynthesized by the coupling of tryptamine and aurantioclavine, two building blocks derived from L-tryptophan. The postmodification steps were mapped by targeted-gene-deletion experiments and the structural elucidation of intermediates and new analogues. Our studies set the stage for the biochemical characterization of communesin biosynthesis. This knowledge will aid our understanding of how nature generates remarkable structural complexity from simple precursors.
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