6-Deoxy-6-hydroxymethyl scyllo-inositol 1,2,4-trisphosphate: A potent agonist at the inositol 1,4,5-trisphosphate receptor

The synthesis of racemic 6-deoxy-6-hydroxymethyl scyllo-inositol 1,2,4-trisphosphate is described. This compound is a highly potent agonist at the platelet -myo-inositol 1,4,5-trisphosphate receptor, and it binds to the rat cerebellar receptor with an affinity equal to that of the natural ligand. These results suggest that the 5″-hydroxymethyl group of adenophostin A may contribute to its unusual potency.