Direct glycosylation of protected O-tritylserine esters and oligopeptides

Andrzej Rajca, Manfred Wiessler

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

N-Fmoc-3-O-Tr-l-serine methyl and benzyl esters, as well as a tripeptide FmocAlaSer(Tr)GlyOBn were directly glycosylated by 3,4,6-tri-O-acetyl-1,2-O-(1-cyanoethylidene)-α-d-galactopyranose in the presence of TrClO4 in dichloromethane, yielding 32-57% of N-Fmoc-3-O-(2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-l-serine esters and the corresponding tripeptide.

Original languageEnglish (US)
Pages (from-to)123-136
Number of pages14
JournalCarbohydrate Research
Volume274
Issue numberC
DOIs
StatePublished - Sep 8 1995

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Keywords

  • Cyanoethylidene condensation
  • Glycosylation
  • N-9-Fluorenylmethoxycarbonyl-O-tritylserine esters
  • Serine glycopeptides
  • Serine glycosides

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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