Synthesis of a truncated bi-antennary complex-type N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases Endo A and Endo M

Thomas B. Parsons, James W. B. Moir, Antony J. Fairbanks

Research output: Contribution to journalArticlepeer-review

Abstract

The synthesis of a truncated complex N-glycan hexasaccharide oxazoline was achieved producing a substrate that was assayed as an activated donor for glycosylation catalysed by the endohexosaminidases Endo A and Endo M. For Endo M competitive product hydrolysis was seen to limit synthetic efficiency. In spite of its natural hydrolytic selectivity wild type Endo A was able to process the truncated complex N-glycan oxazoline, albeit with limited synthetic efficiency; notably the product was not a substrate for Endo A catalysed hydrolysis. Two Endo A mutants, E173Q and E173H, were also assayed, but were unable to process this oxazoline.

Original languageEnglish
Pages (from-to)3128-3140
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume7
Issue number15
DOIs
Publication statusPublished - 2009

Keywords

  • STIMULATING PROTEIN NESP
  • CHEMOENZYMATIC SYNTHESIS
  • LINKED OLIGOSACCHARIDES
  • GLYCOPROTEIN-SYNTHESIS
  • ALLYL ETHERS
  • TRANSGLYCOSYLATION ACTIVITY
  • ACETYLGLUCOSAMINE MOIETIES
  • ARTHROBACTER PROTOPHORMIAE
  • HUMAN-ERYTHROPOIETIN
  • MILD CONDITIONS

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