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Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation

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Published copy (DOI)

Author(s)

  • Thomas W. D. F. Rising
  • Timothy D. W. Claridge
  • Nicola Davies
  • David P. Gamblin
  • James W. B. Moir
  • Antony J. Fairbanks

Department/unit(s)

Publication details

JournalCARBOHYDRATE RESEARCH
DatePublished - 24 Jul 2006
Issue number10
Volume341
Number of pages23
Pages (from-to)1574-1596
Original languageEnglish

Abstract

Oxazoline mono-, di-, tri- and hexasaccharides, corresponding to the core components of N-linked glycoprotein high mannose glycans, are synthesised as potential glycosyl donors for endohexosaminidase catalysed glycosylation of glycopeptides and glycoprotein remodelling. The crucial beta-D-Manp-(1 -> 4)-D-GlcpNAc linkage is synthesised via epimerisation of gluco disaccharide substrates by sequential triflation and nucleophilic substitution. Oxazolines are formed directly from the anomeric OPMP protected N-acetyl glucosamine derivatives. Efficient endohexosaminidase catalysed glycosylation of a synthetic beta-D-GlcpNAcAsn glycosyl amino acid is demonstrated with the trisaccharide oxazoline donor. (c) 2006 Elsevier Ltd. All rights reserved.

    Research areas

  • endoglycosidase, endohexosaminidase, oxazoline, N-glycan, transglycosylation, protein remodelling, SUBSTRATE-ASSISTED CATALYSIS, LINKED SUGAR CHAINS, CHEMOENZYMATIC SYNTHESIS, ACETYLGLUCOSAMINE MOIETIES, COMPLEX-TYPE, OLIGOSACCHARIDES, GLYCOPEPTIDES, TRANSGLYCOSYLATION, MANNOPYRANOSIDES, GLYCOPROTEINS

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