Synthesis of ganglioside analogs containing fluorescently labeled GalNAc for single-molecule imaging

Abstract

Gangliosides, glycosphingolipids containing sialic acid(s) in the glycan moieties, as major constituents of functional membrane domains such as lipid rafts participate in various biological processes. Previously, we developed fluorescent ganglioside analogs useful for single-molecule imaging of lipid raft formations. In this paper, we describe the development of a, 6-N3-GalNTCAc donor and its application to the synthesis of fluorescent gangliosides containing fluorescent GalNAc residue(s) at the glycan terminus, namely, fluorescent analogs of GalNAc-GD1a and asialo-GM2.