Rapid chemo-enzymatic synthesis of peracetylated glcnacβ3galβ- aglycones

N. Merbouh, J. R. Brown, F. K. Wallner, M. Morton, J. D. Esko, P. H. Seeberger

Research output: Contribution to journalArticlepeer-review

Abstract

The inhibition of sialyl Lewis X can prevent unwanted cellular extravasation that is associated with inflammatory diseases and tumor metastasis. Described is an efficient methodology to prepare peracetylated GlcNAcβ3Gal-aglycone disaccharides subsequently used as metabolic decoys to inhibit sialyl Lewis X expression. Four glycosides were synthesized from one single parent disaccharide that in turn was prepared by large-scale enzymatic synthesis. The procedure avoids lengthy and inefficient synthetic steps to afford the desired disaccharides quickly with good overall yields.

Original languageEnglish (US)
Pages (from-to)373-390
Number of pages18
JournalJournal of Carbohydrate Chemistry
Volume30
Issue number4-6
DOIs
StatePublished - 2011

Keywords

  • Decoy
  • Disaccharides
  • Glycosyltransferase
  • Sialyl Lewis X

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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