Synthesis of spacer-containing di- and tri-saccharides that represent parts of the capsular polysaccharide of Streptococcus pneumoniae type 6B

M J Thijssen; M N van Rijswijk; J P Kamerling; J F Vliegenthart

doi:10.1016/s0008-6215(97)00271-1

Synthesis of spacer-containing di- and tri-saccharides that represent parts of the capsular polysaccharide of Streptococcus pneumoniae type 6B

Carbohydr Res. 1998 Jan;306(1-2):93-109. doi: 10.1016/s0008-6215(97)00271-1.

Authors

M J Thijssen¹, M N van Rijswijk, J P Kamerling, J F Vliegenthart

Affiliation

¹ Bijvoet Center, Department of Bio-Organic Chemistry, Utrecht University, Netherlands.

PMID: 9691442
DOI: 10.1016/s0008-6215(97)00271-1

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bacterial Capsules / chemistry*
Carbohydrate Conformation
Carbohydrate Sequence
Disaccharides / chemical synthesis
Disaccharides / chemistry*
Molecular Sequence Data
Polysaccharides, Bacterial / chemistry*
Streptococcus pneumoniae / chemistry*
Trisaccharides / chemical synthesis
Trisaccharides / chemistry*

Substances

Disaccharides
Polysaccharides, Bacterial
Trisaccharides