A highly efficient chemoenzymatic approach toward glycoprotein synthesis

Org Lett. 2006 Jul 6;8(14):3081-4. doi: 10.1021/ol061056m.

Abstract

[reaction: see text] A highly efficient endoglycosidase-catalyzed synthesis of homogeneous glycoproteins is described. By using ribonuclease B as a model system, it was demonstrated that Endo-A could efficiently attach a preassembled oligosaccharide to a GlcNAc-containing protein in a regio- and stereospecific manner, when the corresponding sugar oxazoline was used as the donor substrate. The method allows the synthesis of both natural and tailor-made N-linked glycoproteins in excellent yield.

MeSH terms

  • Carbohydrate Sequence
  • Glycoproteins / biosynthesis*
  • Glycoside Hydrolases / metabolism*
  • Models, Biological
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry

Substances

  • Glycoproteins
  • Oligosaccharides
  • Glycoside Hydrolases