Design and Synthesis of a Doubly Functionalized Core Structure of a Glycosylphosphatidylinositol Anchor Containing Photoreactive and Clickable Functional Groups

A bifunctional derivative of the core structure of glycosylphosphatidylinositol (GPI) anchors having a clickable alkynyl group and a photoreactive diazirine group attached to the GPI glucosamine and lipid moieties, respectively, was synthesized from myo-inositol, d-glucosamine, and (R)-1,2-O-acetonized glycerol. The target molecule should be useful for the investigation of GPI-interacting components in the cell membrane that play a key role in the signal transduction and other biological functions of GPI-anchored proteins.