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The synthesis of L-chiro-inositol 2,3,5-trisphosphorothioate, a novel analogue of the second messenger D-myo-inositol 1,4,5-trisphosphate has been accomplished from the natural product L-quebrachitol. Phosphitylation of (-)-1L-1,4,6-tri-O-benzoyl-chiro-inositol obtained from L-quebrachitol followed by sulfoxidation of the products gave (-)-1L-1,4,6-tri-O-benzoyl-chiro-inositol 2,3,5-tris[di(2-cyanoethyl) phosphorothioate], which was deblocked using sodium in liquid ammonia to give 1L-(-)-chiro-inositol 2,3,5-trisphosphorothioate. 1L-chiro-Inositol 2,3,5-trisphosphorothioate is a partial agonist in the release of intracellular Ca2+ from saponin-permeabilised platelets and is both a key tool for pharmacological dissection of the polyphosphoinositide pathway of cellular signalling and a lead compound for the design of small molecule Ins(1,4,5)P3 receptor antagonists.

Type

Journal article

Journal

Bioorg Med Chem

Publication Date

04/1994

Volume

2

Pages

253 - 257

Keywords

Animals, Blood Platelets, Calcium, Calcium Channels, In Vitro Techniques, Inositol 1,4,5-Trisphosphate, Inositol 1,4,5-Trisphosphate Receptors, Organothiophosphorus Compounds, Rabbits, Receptors, Cytoplasmic and Nuclear, Second Messenger Systems, Stereoisomerism