Synthesis and Molecular Recognition of Phosphatidylinositol-3-methylenephosphate

Abstract

[reaction: see text] Phosphatidylinositol-3-phosphate (PtdIns(3)P) is a spatial regulator of vesicular trafficking and other vital cellular processes. We describe the asymmetric total synthesis of a metabolically stabilized analogue, phosphatidylinositol-3-methylenephosphate (PtdIns(3)MP) from a differentially protected myo-inositol. NMR studies of PtdIns(3)MP bound to the (15)N-labeled FYVE domain showed significant (1)H and (15)N chemical shift changes relative to the unliganded protein.