ArticleJournal of the American Chemical Society2016
Detailed Mechanistic Study of the Non-enzymatic Formation of the Discoipyrrole Family of Natural Products.
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 11 papers.
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Who cites it
11 citing papers in PubMed, 25 citations in OpenAlex.
- Discovery and Theoretical Studies of Nonenzymatic Polyketide Dimerizations of Chaetophenols.Organic letters · 2025Article
- Biomimetic Total Synthesis and Investigation of the Non-Enzymatic Chemistry of Oxazinin A.Angewandte Chemie (International ed. in English) · 2022Article
- Chimeric natural products derived from medermycin and the nature-inspired construction of their polycyclic skeletons.Nature communications · 2022Article
- Boron NMR as a Method to Screen Natural Product Libraries for B-Containing Compounds.Organic letters · 2022Article
- Structure and Biosynthesis of Myxofacyclines: Unique Myxobacterial Polyketides Featuring Varing and Rare HeterocyclesChemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Elucidation and Regulation of Polyphenols in the Smoking Process of Shanxi Aged Vinegar.Foods (Basel, Switzerland) · 2021Article
- Synthesis and Investigation of the Abiotic Formation of Pyonitrins A-D.Organic letters · 2020Article
- Circumdatin-Aspyrone Conjugates from the Coral-AssociatedMarine drugs · 2019Article
- Dual phenazine gene clusters enable diversification during biosynthesis.Nature chemical biology · 2019Article
- Carpatizine, a novel bridged oxazine derivative generated by non-enzymatic reactions.Organic & biomolecular chemistry · 2017Article
- Non-enzymatic pyridine ring formation in the biosynthesis of the rubrolone tropolone alkaloids.Nature communications · 2016Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Discoipyrroles A-D (DPA-DPD) are recently discovered natural products produced by the marine bacterium Bacillus hunanensis that exhibit anticancer properties in vitro. Initial biosynthetic studies demonstrated that DPA is formed in the liquid fermentation medium of B. hunanensis from three secreted metabolites through an unknown but protein-independent mechanism. The increased identification of natural products that depend on non-enzymatic steps creates a significant need to understand how these different reactions can occur. In this work, we utilized (15)N-labeled starting materials and continuous high-sensitivity (1)H-(15)N HMBC NMR spectroscopy to resolve scarce reaction intermediates of the non-enzymatic discoipyrrole reaction as they formed in real time. This information guided supplemental experiments using (13)C- and (18)O-labeled materials to elucidate the details of DPA's non-enzymatic biosynthesis, which features a highly concerted pyrrole formation and necessary O2-mediated oxidation. We have illustrated a novel way of using isotopically enhanced two-dimensional NMR spectroscopy to interrogate reaction mechanisms as they occur. In addition, these findings add to our growing knowledge of how multicomponent non-enzymatic reactions can occur through inherently reactive bacterial metabolites.
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