Synthetic Studies on Selectin Ligands/Inhibitors: Synthesis and Inhibitory Activity of 2-O-Fucosyl Sulfatides Containing 2-Branched Fatty Alkyl Residues in Place of Ceramide

To investigate the biological selectin-ligand interactions, four sulfated 2-O-α-L-fucopyranosyl β-D-galactopyranosides containing 2-branched fatty-alkyl residues in place of ceramide have been systematically synthesized. The target glycolipids were assayed for their ability to block the adhesion of HL-60 cells to immobilized P-, L- and E-selectin. Among them, 2-O-α-L-fucopyranosyl sulfatide, which is anchored with 2-(tetradecyl) hexadecyl residue showed significantly more potency of the blocking adhesion to P- and L-selectins.