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Carbohydr Res. 2010 Oct 13;345(15):2282-6. doi: 10.1016/j.carres.2010.08.002. Epub 2010 Aug 10.

Synthesis of a core disaccharide from the Streptococcus pneumoniae type 23F capsular polysaccharide antigen.

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1
Department of Chemistry, 80 St. George Str. Toronto, ON, Canada.

Abstract

The synthesis of methyl α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranoside and methyl α-l-rhamnopyranosyl-(1→2)-3-(glycer-2-yl-phosphate)-β-d-galactopyranoside disaccharides from the Streptococcuspneumoniae type 23F capsular polysaccharide is reported. A simple protecting group strategy was followed using commercially available monosaccharides and phosphorylating reagents. H-Phosphonate and phosphoramidite coupling chemistries were explored for introducing the phosphodiester. Hydrazine hydrate was found to be a mild and efficient deacetylating agent, which was required to avoid phosphate migration during the deprotection of the phosphodiester functionalized disaccharide.

PMID:
20810102
DOI:
10.1016/j.carres.2010.08.002
[Indexed for MEDLINE]

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