Efficient synthesis of β-(1,6)-linked oligosaccharides through microwave-assisted glycosylation

Lingyao Li, Emily A. Franckowiak, Yi Xu, Evan McClain, Wenjun Du

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

A microwave-assisted glycosylation method was developed for efficient synthesis of oligosaccharides. Di-functional AB monomers, 2,3,4-tri-O-acetyl- α-d-galactopyranosyl bromide (3a) and 2,3,4-tri-O-acetyl-α-d- glucopyranosyl bromide (3b) were designed and synthesized as weakly reactive monomers to avoid unwanted glycosylation or degradation during preparation and storage. The glycosylations of these monomers gave low conversions and low molecular weight oligosaccharides at rt, reflux, and under low microwave energy irradiation. However, the glycosylation became very effective when high microwave energy was applied, giving 100% conversion and producing oligosaccharides with Mn = 4.76 kDa for 3a and Mn = 4.05 kDa for 3b. The acetylated oligosaccharides were further subjected to deprotection for structural analysis, which indicated the oligosaccharides contain predominantly linear β-(1,6)-glycosyl linkages.

Original languageEnglish
Pages (from-to)3693-3699
Number of pages7
JournalJournal of Polymer Science, Part A: Polymer Chemistry
Volume51
Issue number17
DOIs
StatePublished - Sep 1 2013

Keywords

  • NMR
  • glycosyl bromide
  • glycosylation
  • microwave
  • oligosaccharides
  • polysaccharides
  • synthesis

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