The chemo-enzymatic synthesis is described of β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→O(CH(2))(6)NH(2) (1), β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp-(1→O(CH(2))(6)NH(2) (2), β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp-(1→O(CH(2))(6)NH(2) (3), and β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp -(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc-(1→O(CH(2))(6)NH(2) (4), representing fragments of the repeating unit of the Streptococcus pneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk β-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models.
carbohydrates, Streptococcus pneumoniae, oligosaccharide synthesis
NCBI PubMed ID: 14670722Publication DOI: 10.1016/s0008-6215(03)00292-1Journal 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