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-galactopy ranoside 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.
Streptococcus pneumoniae, H-phosphonate, phosphoramidite, Phosphoglycan
NCBI PubMed ID: 20810102Publication DOI: 10.1016/j.carres.2010.08.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: M. Nitz
Institutions: Department of Chemistry, 80 St. George Str. Toronto, ON, Canada
Methods: NMR, chemical synthesis
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