SYNTHESIS AND CHARACTERIZATION OF A C-13-LABELED ALPHA-MANNOSYL GLYCOLIPID ANALOG FROM [C-13]GLUCOSE

A method is described for the synthesis of a [C-13]alpha-mannosyl glyc olipid analog from [C-13]glucose. After acetylation and reduction of g lucose (U-C-13(6), 30%) to tri-O-acetyl-D-glucal (U-C-13(6), 30%), add ition of the nucleophile [2-[2-(tetradecyloxy)ethoxy]ethoxy]ethoxy]-et hanol (tetra-decyltetraglycol) yields the rearrangement product alpha- tetradecyl-tetraglycol 2,3-dideoxy-4,6-di-O-acetyl-D-gluco- pyranoside (U-C-13(6), 30%). The rearrangement product is oxidized with osmium t etroxide to produce tetradecyltetraglycol alpha-mannoside (U- C-13(6), 30%). The interaction of the glycolipid with the plant lectin concana valin A is characterized by a vesicle agglutination assay.