Synthesis of phosphonate derivatives of myo-inositol for use in biochemical studies of inositol-binding proteins

Abstract Phospholipids containing the inositol headgroup (phosphoinositides) serve as membrane storage forms of a family of messenger molecules that transmit signals in cells. In this study a general synthesis of myo -inositol phosphate derivatives in which the posphorus oxygen bond is replaced with a phosphorus carbon bond (i.e. phosphonates) is presented. Four specific examples of phosphonate analogs of phosphatidylinositol (PI) are prepared which have a single alkyl chain in place of the diacylglycerol. These derivatives are stable in neutral and alkaline solutions and are designed for use in biochemical studies of PI-specific phospholipases C and other enzymes involved in the phosphoinositide signal transduction pathway.