Chemo-enzymatic synthesis of a tetra- and octasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 14

Carbohydr Res. 2003 Nov 14;338(23):2611-27. doi: 10.1016/s0008-6215(03)00313-6.

Abstract

The chemo-enzymatic synthesis is described of tetrasaccharide beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-GlcpNAc-(1-->O(CH(2))(6)NH(2) (1) and octasaccharide beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-GlcpNAc-(1-->O(CH(2))(6)NH(2) (2), representing one and two tetrasaccharide repeating units of Streptococcus pneumoniae serotype 14 capsular polysaccharide. In a chemical approach, the intermediate linear trisaccharide 3 and hexasaccharide 4 were synthesized. Galactose residues were beta-(1-->4)-connected to the internal N-acetyl-beta-D-glucosamine residues by using bovine milk beta-1,4-galactosyltransferase. Both title oligosaccharides will be conjugated to carrier proteins to be tested as potential vaccines in animal models.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Carbohydrate Sequence
  • Carbohydrates / chemistry
  • Cattle
  • Glucosamine / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • N-Acetyllactosamine Synthase / metabolism
  • Polysaccharides / chemical synthesis
  • Polysaccharides, Bacterial / chemistry*
  • Streptococcus pneumoniae / metabolism*
  • Temperature

Substances

  • Carbohydrates
  • Polysaccharides
  • Polysaccharides, Bacterial
  • N-Acetyllactosamine Synthase
  • Glucosamine