In the framework of studies towards oligosaccharide-conjugate based vaccines against Streptococcus pneumoniae, the synthesis is reported of four spacer-containing tetrasaccharides that each can be conceived as representing a repeating unit of the capsular polysaccharide of S. pneumoniae serotype 6B, namely, 3-aminopropyl D-ribityl-(5→hydrogen phosphate→2)-α-D-galactopyranosyl-(1→3)-α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranoside, 3-aminopropyl α-L-rhamnopyranosyl-(1→4)-D-ribityl-5(→hydrogen phosphate→2)-α-D-galactopyranosyl-(1→3)-α-D-glucopyranoside, 3-aminopropyl α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-D-ribityl-(5→hydrogen phosphate→2)-α-D-galactopyranoside, and α-D-galactopyranosyl-(1→3)-α-D-glucopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→4)-5-O-(3-aminopropyl hydrogen phosphate)-D-ribitol. Phosphorylations were carried out using the H-phosphonate method.
synthesis, tetrasaccharide, capsular, polysaccharide, Streptococcus, Streptococcus pneumoniae, repeating unit, capsular polysaccharide, type, phosphorylated oligosaccharide, Streptococcus pneumoniae 6B, vaccines
NCBI PubMed ID: 9691443Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Bijuoet Center, Department of Bio-Organic Chemistry, Utrecht University, Utrecht, The Netherlands
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