Glycosylation of α-amino acids by sugar acetate donors with InBr 3. Minimally competent Lewis acids

Mark R. Lefever, Lajos Z. Szab, Bobbi Anglin, Michael Ferracane, Joanna Hogan, Lauren Cooney, Robin Polt

Research output: Contribution to journalArticle

16 Scopus citations

Abstract

A simplified method for the preparation of Fmoc-serine and Fmoc-threonine glycosides for use in O-linked glycopeptide synthesis is described. Lewis acids promote glycoside formation, but also promote undesired reactions of the glycoside products. Use of 'minimally competent' Lewis acids such as InBr 3 promotes the desired activation catalytically, and with greatly reduced side products from sugar peracetates.

Original languageEnglish (US)
Pages (from-to)121-125
Number of pages5
JournalCarbohydrate Research
Volume351
DOIs
StatePublished - Apr 1 2012

Keywords

  • Glycosylation
  • Indium tribromide
  • O-linked glycopeptides
  • Serine
  • Threonine

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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