ArticleChemistry, an Asian journal2024
Synthesis of Saxitoxin Biosynthetic Intermediates: Reveal the Mechanism for Formation of its Tricyclic Skeleton in Biosynthesis.
Article in Chemistry, an Asian journal, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- Total Syntheses of Agelamadin F and (±)-Tauroacidin A, Enabled by NaClOChemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Hemolymph-Mediated Dynamics of Paralytic Shellfish Toxins and Tetrodotoxin in Scallops.Marine drugs · 2026Article
- Total Synthesis and Structural Revision of (±)-Mauritamide B.Journal of natural products · 2025Article
- Synthesis of Saxitoxin Biosynthetic Intermediates: Reveal the Mechanism for Formation of its Tricyclic Skeleton in Biosynthesis.Chemistry, an Asian journal · 2024Article
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Authors and funding
9 authors.
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Abstract
The synthesis and biosynthesis of the complex saxitoxin (STX) structure have garnered significant interest. Previously, we hypothesized that the tricyclic skeleton of STX originates from the monocyclic precursor 11-hydroxy-IntC'2 during biosynthesis, although direct evidence has been lacking. In this study, we identified conditions to synthesize a proposed tricyclic biosynthetic intermediate, 12,12-dideoxy-decarbamoyloxySTX (dd-doSTX), along with its 6-epimer (6-epi-dd-doSTX) and a bicyclic compound, in a single step from di-Boc protected 11-hydroxy-IntC'2. The reaction mechanism involves successive aza-Michael addition of a guanidino amine to the conjugated olefin. Notably, both dd-doSTX and 6-epi-dd-doSTX were detected in a toxin-producing cyanobacterium, suggesting that the biosynthetic enzymes may generate these compounds via similar mechanisms.
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