The chemo-enzymatic synthesis is described of tetrasaccharide β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpN Ac-(1→O(CH(2))(6)NH(2) (1) and octasaccharide β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpN Ac-(1→3)-β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-βD-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 β-(1→4)-connected to the internal N-acetyl-β-D-glucosamine residues by using bovine milk β-1,4-galactosyltransferase. Both title oligosaccharides will be conjugated to carrier proteins to be tested as potential vaccines in animal models.
carbohydrates, Streptococcus pneumoniae, oligosaccharide synthesis
NCBI PubMed ID: 14670721Publication DOI: 10.1016/s0008-6215(03)00313-6Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: j.p.kamerling@chem.uu.nl
Institutions: Bijvoet Center, Department of Bio-Organic Chemistry, Section of Glycoscience and Biocatalysis, Utrecht University, Utrecht, the Netherlands
Found