Chemical Synthesis of the O-Antigen Repeating Unit of Escherichia coli O86 by an N-Formylmorpholine-Modulated One-Pot Glycosylation Strategy

Arun B. Ingle, Chin Sheng Chao, Wei Cheng Hung, Kwok-Kong Mong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The synthesis of the O-antigen pentasaccharide repeating unit of the cell wall of Gram-negative bacteria Escherichia coli O86 is reported. The synthesis features the use of an N-formylmorpholine (NFM)-modulated glycosylation method for the construction of 1,2-cis α-glycosidic linkages and an [1+1+2] iterative one-pot α-glycosylation strategy to accelerate the assembly of the tetrasaccharide backbone.

Original languageEnglish
Pages (from-to)870-876
Number of pages7
JournalAsian Journal of Organic Chemistry
Volume3
Issue number8
DOIs
StatePublished - 1 Aug 2014

Keywords

  • Escherichia coli O86
  • Glycosylation
  • O-antigen
  • Oligosaccharides
  • Total synthesis

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