Synthesis of Inositol Polyphosphates

Abstract

Synthesis of optically active D-myo-inositol 1, 4, 5-trisphosphate (Ins (1, 4, 5) P3), and its metabolites, Ins (1, 3, 4) P3, Ins (1, 2-cyclic, 4, 5) P3, and Ins (1, 3, 4, 5) P4 which are involved in an intracellular signal transduction system were accomplished starting from myo-inositol. In the process of these synthesis, two phosphorylation methods of vicinal diols and sterically hindered alcohols were devised. That is, combination of tetrabenzyl pyrophosphate and butyllithium was found to be an efficient phosphorylation reagent. The other is the stepwise phosphorylation which employs phosphorus trichloride, benzyl alcohol, and t-butyl hydroperoxide successively. For the optical resolution, diastereomeric menthoxyacetic esters and chiral column were effectively employed. © 1989, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.