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

Hongbin Sun, Jingsong Yang, Katie E. Amaral, Benjamin A. Horenstein

29 Scopus citations

Abstract

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 kinetic studies show that 3a/3b exhibit significant inhibition on both 2,3- and 2,6-sialytransferases.

Original languageEnglish (US)
Pages (from-to)2451-2453
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number13
DOIs
Publication statusPublished - Mar 26 2001

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this