ArticleNature communications2023
C5 methylation confers accessibility, stability and selectivity to picrotoxinin.
Article in Nature communications, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
6 citing papers in PubMed, 13 citations in OpenAlex.
- Article
- Decoding Guaianolide Biosynthesis: Synthetic Insights into Pseudoguaianolides and Seco-Guaianolides.Organic letters · 2025Article
- How to Tell an N from an O: Controlling the Chemoselectivity of Methyltransferases.ACS catalysis · 2025Article
- Computational workflow limits need to 'guess and check' in the synthesis of complex molecules.Nature · 2025Article
- Article
- Natural Product Synthesis in the 21st Century: Beyond the Mountain Top.ACS central science · 2024Review
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Authors and funding
9 authors at 4 institutions in 1 country.
Funding
Abstract
Minor changes to complex structures can exert major influences on synthesis strategy and functional properties. Here we explore two parallel series of picrotoxinin (PXN, 1) analogs and identify leads with selectivity between mammalian and insect ion channels. These are the first SAR studies of PXN despite its >100-year history and are made possible by advances in total synthesis. We observe a remarkable stabilizing effect of a C5 methyl, which completely blocks C15 alcoholysis via destabilization of an intermediate twist-boat conformer; suppression of this secondary hydrolysis pathway increases half-life in plasma. C5 methylation also decreases potency against vertebrate ion channels (γ-Aminobutyric acid type A (GABA
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