SYNTHESIS OF ENANTIOMERICALLY PURE LYSOPHOSPHATIDYLINOSITOLS AND ALKYLPHOSPHOINOSITOLS

A convenient synthesis for enantiomeric pure 1-O-(1'-O-alkyl-sn-glycero-3'-phospho)-D (or L)-myo-inositol, 1-O-(1'-O-acyl-sn-glycero-3'-phospho)-D (or L)-Myo-inositol and alkylphospho-1-D (or L)-myo-inositol has been described. Starting from myo-inositol, penta-O-acetyl-myo-inositol was made in five steps. Then enantiomeric purification was done by a diastereomeric salts separation method, and the purity of each enantiomer was spectroscopically measured (F-19-NMR). The phosphodiester was made via phosphoramidites. The enantiomeric products (> 99% optical purity) of all compounds were easily obtained in large quantities (5-10 g). Synthetic phosphatidylinositol analogues of precisely defined structure and configuration are interesting tools for studying signal transduction mechanism and cell activity modulation.