1998 Volume 46 Issue 5 Pages 797-806
To investigate the biological selectin-ligand interactions, fourteen sulfated and eight phosphorylated β-D-galaco- and lactopyranosides containing branched fatty-alkyl residues in place of the ceramide have been synthesized. Regioselective sulfation of the parent glycolipids through the dibutylstannylene acetal with a certain amount of sulfur trioxide-trimethylamine complex produced the target sulfated glycolipids, while stepwise phosphorylation by treatment of the properly protected diol with dibenzyloxy(diisopropylamino)phosphine gave the phosphorylated glycolipids. The synthetic glycolipids showed an interesting mode of inhibition of the binding of HL-60 cells to immobilize P-, L- and E-selectins during in vitro experiments. In addition, using computer modeling techniques, we examined the molecular basis for the ligand-selectin complex formation. These glycolipids may be useful as therapeutic agents against selectin-dependent inflammation.