S. Sato, R. Sakai, M. Kodama
Aug 21, 2000
Citations
2
Influential Citations
42
Citations
Journal
Bioorganic & medicinal chemistry letters
Abstract
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.