Synthesis of inositol phosphoglycans and analogues thereof

Abstract: This thesis describes the synthesis of inositol phosphoglycans (IPG) corresponding to glycosyl-phosphatidylinositol (GPI) anchors found on the cell surface of the parasite Leishmania. Synthesis of an IPG which is a putative second messenger for insulin, and of analogues thereof is also discussed.The IPG structures synthesized contain mono-, tri-, and hexasaccharides linked to an inositol phosphate. Analogues of the putative second messenger contain glucosamine, instead of myo-inositol phosphate, coupled to either phosphorylated D-mannose or phosphorylated L-fucose. The synthetic work involved the development of procedures for obtaining optically pure myo-inositol-glucosamine derivatives, the formation of phosphomono- and diesters (both cyclic and acyclic) and oligosaccharide synthesis.