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Chemical synthesis and actions of 11,12-thiirano-hepoxilin A3
P M Demin1, D Reynaud, C R Pace-Asciak
1Research Institute, The Hospital for Sick Children, Toronto, Canada.
Journal of Lipid Mediators and Cell Signalling
|January 1, 1996
Abstract:
A novel analog of hepoxilin A3 has been chemically synthesized in which the 11,12-epoxide group has been altered to a thiirano group. This has been accomplished through allylic rearrangement of unnatural (11 R, 12 R)-hepoxilin B3 under Mitsunobu conditions, first into unnatural (11 R, 12 R)-hepoxilin A3, followed by conversion of this compound with inversion of the epoxide centers into the thiirano-hepoxilin A3 having the natural 11 S, 12 S configuration. We also report herein evidence showing that thiirano-hepoxilin A3 raises intracellular calcium concentrations in intact human neutrophils.