AN EFFICIENT AND STRAIGHTFORWARD SYNTHESIS OF SIALYL Le ^X GLYCOLIPID AS A POTENT SELECTIN BLOCKER[[1]]

Abstract

An efficient synthesis of sialyl Lewis X (sLe^x) glycolipid as a potent selectin blocker is described. 2-(Tetradecyl)hexadecanol which functions as an artificial ceramide, was glycosylated with phenyl 4-O-acetyl-6-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-2-phthalimido-1-thio-β-d-glucopyranoside at the first step of the synthetic scheme. The N-acetylglucosamine acceptor carrying the hydrophobic aglycon was then coupled with sialyl-α-(2→3)galactose donor to afford the trisaccharide which upon successive α-l-fucosylation and deprotections, resulted in sLe^x glycolipid in quite straightforward steps.

Keywords:

• Sialyl Lewis X
• Selectin
• Glycolipid

ACKNOWLEDGMENTS

This work was supported in part by Grants-in-Aid (No. 12306007) for Scientific Research from the Ministry of Education, Science, and Culture of Japan, and Japan Society for Promotion of Science. We are grateful to Sanwa Kagaku Kenkyusho for FABMS analysis.