Synthesis of a new transition-state analog of the sialyl donor. Inhibition of sialyltransferases

摘要

A new class of glycosyltransferase inhibitor has been designed and synthesized. The designed inhibitors 3a/3b provide conformational mimicry of the transition state in sialyltransfer reactions. The key synthetic steps involve a Meinwald rearrangement and a palladium-catalyzed carbonylation reaction. The results of kineticf studies show that 3a/3b exhibit signficant inhibition on both 2,3- and 2,6-sialyltransferases.