Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers

Article abstract of DOI:10.1039/b007267m

The chemical synthesis of naturally occurring phosphatidylinositol 3,4,5-triphosphate [PtdIns(3,4,5)P₃] and its diastereoisomers was discussed. In the first stage, the preparation of the required enantiomeric 1,2-di-O-acylglycerol derivatives was done. The second stage involved the preparation of suitably protected enantiomeric myo-inositol 1-phosphates. The glycerol and inositol building blocks were coupled together and the 3-, 4- and 5-hydroxy functions of the inositol residues in the coupled products were phosphorylated. Finally, the protecting groups were removed to give PtdIns(3,4,5)P₃ and its diastereoisomers.