ArticleJournal of the American Chemical Society2015
Hapalindole/Ambiguine Biogenesis Is Mediated by a Cope Rearrangement, C-C Bond-Forming Cascade.
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 27 papers.
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Who cites it
27 citing papers in PubMed.
- Hapalindole Q suppresses autophagosome-lysosome fusion by promoting YAP1 degradation via chaperon-mediated autophagy.Proceedings of the National Academy of Sciences of the United States of America · 2024Article
- Biosynthesis of Isonitrile- and Alkyne-Containing Natural Products.Annual review of chemical and biomolecular engineering · 2022Review
- Cyanobacterial secondary metabolites towards improved commercial significance through multiomics approaches.World journal of microbiology & biotechnology · 2022Review
- Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.Natural product reports · 2021Review
- Bacterial terpenome.Natural product reports · 2021Review
- Structural diversification of hapalindole and fischerindole natural products via cascade biocatalysis.ACS catalysis · 2021Article
- Biocatalysts from cyanobacterial hapalindole pathway afford antivirulent isonitriles against MRSA.Journal of biosciences · 2021Article
- Multicomponent Microscale Biosynthesis of Unnatural Cyanobacterial Indole Alkaloids.ACS synthetic biology · 2020Article
- Control of Stereoselectivity in Diverse Hapalindole Metabolites is Mediated by Cofactor-Induced Combinatorial Pairing of Stig Cyclases.Angewandte Chemie (International ed. in English) · 2020Article
- Terpene synthases in disguise: enzymology, structure, and opportunities of non-canonical terpene synthases.Natural product reports · 2020Review
- EvoMining reveals the origin and fate of natural product biosynthetic enzymes.Microbial genomics · 2019Article
- Engineered Production of Hapalindole Alkaloids in the CyanobacteriumACS synthetic biology · 2019Article
- The hidden enzymology of bacterial natural product biosynthesis.Nature reviews. Chemistry · 2019Article
- The expanding world of biosynthetic pericyclases: cooperation of experiment and theory for discovery.Natural product reports · 2019Review
- Enzymatic Cascade Reactions in Biosynthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Structural insights into the calcium dependence of Stig cyclases.RSC advances · 2019Article
- Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.Journal of the American Chemical Society · 2019Article
- Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis.Beilstein journal of organic chemistry · 2019Review
- Recent Advances in Enzymatic Complexity Generation: Cyclization Reactions.Biochemistry · 2018Review
- Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis.Nature chemical biology · 2018Article
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Authors and funding
9 authors.
Funding
Abstract
Hapalindoles are bioactive indole alkaloids with fascinating polycyclic ring systems whose biosynthetic assembly mechanism has remained unknown since their initial discovery in the 1980s. In this study, we describe the fam gene cluster from the cyanobacterium Fischerella ambigua UTEX 1903 encoding hapalindole and ambiguine biosynthesis along with the characterization of two aromatic prenyltransferases, FamD1 and FamD2, and a previously undescribed cyclase, FamC1. These studies demonstrate that FamD2 and FamC1 act in concert to form the tetracyclic core ring system of the hapalindoles from cis-indole isonitrile and geranyl pyrophosphate through a presumed biosynthetic Cope rearrangement and subsequent 6-exo-trig cyclization/electrophilic aromatic substitution reaction.
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