ArticleNature chemical biology2018
Structural basis of the Cope rearrangement and cyclization in hapalindole biogenesis.
Article in Nature chemical biology, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 45 citations in OpenAlex.
- 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
- Total synthesis, biological evaluation and biosynthetic re-evaluation ofChemical science · 2024Article
- Designing solvent systems using self-evolving solubility databases and graph neural networks.Chemical science · 2024Article
- Biosynthesis of Polycyclic Natural Products from Conjugated Polyenes via Tandem Isomerization and Pericyclic Reactions.Journal of the American Chemical Society · 2023Article
- Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.Natural product reports · 2021Review
- Microbial soluble aromatic prenyltransferases for engineered biosynthesis.Synthetic and systems biotechnology · 2021Article
- Structural diversification of hapalindole and fischerindole natural products via cascade biocatalysis.ACS catalysis · 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
- Structural basis for stereoselective dehydration and hydrogen-bonding catalysis by the SAM-dependent pericyclase LepI.Nature chemistry · 2019Article
- Engineered Production of Hapalindole Alkaloids in the CyanobacteriumACS synthetic biology · 2019Article
- The hidden enzymology of bacterial natural product biosynthesis.Nature reviews. Chemistry · 2019Article
- Enzymatic Cascade Reactions in Biosynthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Structural insights into the calcium dependence of Stig cyclases.RSC advances · 2019Article
- Molecular basis for the plasticity of aromatic prenyltransferases in hapalindole biosynthesis.Beilstein journal of organic chemistry · 2019Review
- The Energetic Viability of Δ¹-Piperideine Dimerization in Lysine-derived Alkaloid Biosynthesis.Metabolites · 2018Article
- PKS-NRPS Enzymology and Structural Biology: Considerations in Protein Production.Methods in enzymology · 2018Article
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Authors and funding
11 authors at 3 institutions in 1 country.
Funding
Abstract
Hapalindole alkaloids are a structurally diverse class of cyanobacterial natural products defined by their varied polycyclic ring systems and diverse biological activities. These complex metabolites are generated from a common biosynthetic intermediate by the Stig cyclases in three mechanistic steps: a rare Cope rearrangement, 6-exo-trig cyclization, and electrophilic aromatic substitution. Here we report the structure of HpiC1, a Stig cyclase that catalyzes the formation of 12-epi-hapalindole U in vitro. The 1.5-Å structure revealed a dimeric assembly with two calcium ions per monomer and with the active sites located at the distal ends of the protein dimer. Mutational analysis and computational methods uncovered key residues for an acid-catalyzed [3,3]-sigmatropic rearrangement, as well as specific determinants that control the position of terminal electrophilic aromatic substitution, leading to a switch from hapalindole to fischerindole alkaloids.
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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.