ArticleJournal of the American Chemical Society2021
Structure Revision of the Lomaiviticins.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 26 papers.
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Who cites it
26 citing papers in PubMed.
- Total Synthesis and Structural Revision of Rhabdobranin Reveals a Cryptic Gram-Negative Antibiotic.Journal of the American Chemical Society · 2026Article
- Rapid Structural Analysis of Natural Products Using MicroED.Small (Weinheim an der Bergstrasse, Germany) · 2026Article
- Genome Mining-Based Discovery of Pyrano[2,3-Organic letters · 2025Article
- Microcrystal Electron Diffraction-Guided Discovery of Fungal Metabolites.Journal of the American Chemical Society · 2025Article
- Standards for MicroED.Acta crystallographica. Section C, Structural chemistry · 2025Article
- A new heme enzyme family forms hydrazine groups in diverse biosynthetic pathways.bioRxiv : the preprint server for biology · 2025Article
- Comprehensive microcrystal electron diffraction sample preparation for cryo-EM.Nature protocols · 2025Review
- Isolation, Structure Elucidation and Biological Evaluation of Lomaiviticins F-H, Dimeric Benzofluorene Glycosides from Marine-DerivedMarine drugs · 2025Article
- A Stereoselective Oxidative Dimerization En Route to (-)-Lomaiviticin A.Organic letters · 2025Article
- Applying 3D ED/MicroED workflows toward the next frontiers.Acta crystallographica. Section C, Structural chemistry · 2024Article
- Advances and applications of microcrystal electron diffraction (MicroED).Current opinion in structural biology · 2024Review
- High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED.ACS central science · 2024Article
- Unravelling key enzymatic steps in C-ring cleavage during angucycline biosynthesis.Communications chemistry · 2023Article
- Distinct Conformations of Mirabegron Determined by MicroED.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2023Article
- New Insights on Biological Activities, Chemical Compositions, and Classifications of Marine Actinomycetes Antifouling Agents.Microorganisms · 2023Review
- Structure Elucidation of Secondary Metabolites: Current Frontiers and Lingering Pitfalls.Accounts of chemical research · 2023Article
- On the Abundance and Stability of Diazo-Containing Secondary Metabolites: Enantioselective Synthesis of (-)-Nenestatin A.Organic letters · 2023Article
- MicroED in drug discovery.Current opinion in structural biology · 2023Review
- Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications.Chemical reviews · 2023Review
- Electron Diffraction of 3D Molecular Crystals.Chemical reviews · 2022Review
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Authors and funding
8 authors.
Funding
Abstract
The lomaiviticins are dimeric genotoxic metabolites that contain unusual diazocyclopentadiene functional groups and 2-4 deoxyglycoside residues. Because only 6 of 19 carbon atoms in the monomeric aglycon unit are proton-attached, their structure determination by NMR spectroscopic analysis is difficult. Prior structure elucidation efforts established that the two halves of the lomaiviticins are joined by a single carbon-carbon bond appended to an oxidized cyclohexenone ring. This ring was believed to comprise a 4,5-dihydroxycyclohex-2-ene-1-one. The bridging bond was positioned at C6. This structure proposal has not been tested because no lomaiviticin has been prepared by total chemical synthesis or successfully analyzed by X-ray crystallography. Here, we disclose microED studies which establish that (-)-lomaiviticin C contains a 4,6-dihydroxy-cyclohex-2-ene-1-one residue, that the bridging carbon-carbon bond is located at C5, and that the orientation of the cyclohexenone ring and configuration of the secondary glycoside are reversed, relative to their original assignment. High-field (800 MHz) NMR analysis supports the revised assignment and suggests earlier efforts were misled by a combination of a near-zero
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