Synthesis of spacer-containing di- and tri-saccharides that represent parts of the capsular polysaccharide of Streptococcus pneumoniae type 6B.
In the framework of studies towards oligosaccharide-conjugate-based vaccines against Streptococcus pneumoniae, the synthesis is reported of several spacer-containing oligosaccharides that represent parts of the capsular polysaccharide of S. pneumoniae serotype 6B, namely alpha-L-rhamnopyranosyl-(1-->4)-5-O-(3-aminopropyl hydrogen phosphate)-D-ribitol, 3-aminopropyl D-ribitol-(5-->hydrogen phosphate-->2)-alpha-D-galactopyranoside, 3-aminopropyl alpha-L-rhamnopyranosyl-(1-->4)-D-ribityl-(5-->hydrogen phosphate-->2) -alpha-D-galactopyranoside, and 3-aminopropyl D-ribityl-(5-->hydrogen phosphate-->2) -alpha-D-galactopyranosyl-(1-->3)-alpha-D-glucopyranoside. Phosphorylations were carried out using the H-phosphonate method.
Thijssen
M J
MJ
Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Netherlands.
van Rijswijk
M N
MN
Kamerling
J P
JP
Vliegenthart
J F
JF
D016667:Bacterial Capsules / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D008969:Molecular Sequence Data; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D013296:Streptococcus pneumoniae / Q000737:chemistry*; D014312:Trisaccharides / Q000138:chemical synthesis / Q000737:chemistry*
D004187:Disaccharides; D011135:Polysaccharides, Bacterial; D014312:Trisaccharides