Synthesis and characterization of a 13C-labeled alpha-mannosyl glycolipid analog from [13C]glucose

A method is described for the synthesis of a [13C]alpha-mannosyl glycolipid analog from [13C]glucose. After acetylation and reduction of glucose (U-13C6, 30%) to tri-O-acetyl-D-glucal (U-13C6, 30%), addition of the nucleophile 2-[2-[2-[2-(tetradecyloxy)ethoxy]ethoxy]ethoxy]- ethanol (tetra-decyltetraglycol) yields the rearrangement product alpha-tetradecyltetraglycol 2,3-dideoxyl-4,6-di-O-acetyl-D-gluco- pyranoside (U-13C6, 30%). The rearrangement product is oxidized with osmium tetroxide to produce tetradecyltetraglycol alpha-mannoside (U-13C6, 30%). The interaction of the glycolipid with the plant lectin concanavalin A is characterized by a vesicle agglutination assay.