In:
Canadian Journal of Chemistry, Canadian Science Publishing, Vol. 80, No. 1 ( 2002-01-01), p. 76-81
Abstract:
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 β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text] 3)-β-D-GlcpA-(1[Formula: see text]4)-β-D- Glcp-(1[Formula: see text] 3)-β-D-GlcpA-(1[Formula: see text]4)-β-D-Glcp-(1[Formula: see text] 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.
Type of Medium:
Online Resource
ISSN:
0008-4042
,
1480-3291
Language:
English
Publisher:
Canadian Science Publishing
Publication Date:
2002
detail.hit.zdb_id:
1482256-8
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