Referenced in: none

Automatically associated channels: Kir2.3

Title: Synthesis of 1L-chiro-inositol 2,3,5-trisphosphorothioate, the first partial agonist at the platelet myo-inositol 1,4,5-trisphosphate receptor.

Authors: C Liu, J al-Hafidh, J Westwick, B V Potter

Journal, date & volume: Bioorg. Med. Chem., 1994 Apr , 2, 253-7

PubMed link: http://www.ncbi.nlm.nih.gov/pubmed/7922136

Abstract
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.