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

Carbohydr Res. 2006 Jul 24;341(10):1574-96. doi: 10.1016/j.carres.2006.03.007. Epub 2006 Apr 11.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase / metabolism*
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oxazoles / chemical synthesis*
  • Polysaccharides / chemical synthesis*

Substances

  • Oligosaccharides
  • Oxazoles
  • Polysaccharides
  • Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase