Synthesis of a hexasaccharide fragment of the capsular polysaccharide of Streptococcus pneumoniae type 3

• Published in: Canadian journal of chemistry Vol. 80; no. 1; pp. 76 - 81
• Main Authors: Lefeber, Dirk J, Arévalo, Eneko Aldaba, Kamerling, Johannis P, Vliegenthart, Johannes FG
• Format: Journal Article
• Language: English
• Published: Ottawa, Canada NRC Research Press 01-01-2002; Canadian Science Publishing NRC Research Press
• Subjects: Chemical reactions; Organic chemicals; Oxidation; Pneumonia; Prevention; Streptococcus infections; Streptococcus pneumoniae; Synthesis (chemical); Vaccines
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v01-190

In the framework of the development of a new generation of neoglycoconjugate vaccines against Streptococcus pneumoniae, the synthesis is described of a spacer-containing hexasaccharide fragment related to the capsular polysaccharide of S. pneumoniae type 3. Hexasaccharide -
D
-GlcpA-(1
4)- -
D
-Glcp-(1
3)- -
D
-GlcpA-(1
4)- -
D
- Glcp-(1
3)- -
D
-GlcpA-(1
4)- -
D
-Glcp-(1
O-(CH
2
)
3
NH
2
) (
1
), comprised of three repeating units, was synthesized via a blockwise strategy employing suitably protected disaccharide building blocks. Carboxylic groups were introduced by selective oxidation with TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) in the last reaction steps. Deprotection afforded target hexasaccharide
1
.Key words: oligosaccharide synthesis, Streptococcus pneumoniae type 3, TEMPO oxidation.