Identification of thioether intermediates in the reductive transformation of gonyautoxins into saxitoxins by thiols

O-Sulfate group of gonyautoxin I and IV is transformed into methylene to form neosaxitoxin by thiols such as glutathione, a common cellular scavenger, in mild conditions. We isolated the intermediate of this conversion and propose that this reaction proceeds through formation of thiohemiketal, 1,2 s...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2000-08, Vol.10 (16), p.1787-1789
Main Authors: Sato, Shigeru, Sakai, Ryuichi, Kodama, Masaaki
Format: Article
Language:English
Subjects:
Animals
Chemistry
Exact sciences and technology
Glutathione - chemistry
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Humans
Hydrogen-Ion Concentration
Marine Toxins - biosynthesis
Marine Toxins - chemistry
Mercaptoethanol - chemistry
Molecular Structure
Organic chemistry
Oxidation-Reduction
Preparations and properties
Saxitoxin - analogs & derivatives
Saxitoxin - biosynthesis
Saxitoxin - chemistry
Sulfides - chemistry
Sulfides - metabolism
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Summary:O-Sulfate group of gonyautoxin I and IV is transformed into methylene to form neosaxitoxin by thiols such as glutathione, a common cellular scavenger, in mild conditions. We isolated the intermediate of this conversion and propose that this reaction proceeds through formation of thiohemiketal, 1,2 shift to form stable thioether intermediate, and then redox exchange at sulfur atom to form the final product.
ISSN:0960-894X
1464-3405
DOI:10.1016/S0960-894X(00)00332-2