Synthesis of a Structural Analogue of the Repeating
Unit from <i>Streptococcus pneumoniae</i> 19F Capsular Polysaccharide
Based on the Cross-Metathesis–Selenocyclization Reaction Sequence
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Abstract
Pseudo-oligosaccharides
have attracted much interest as scaffolds
for the synthesis of sugar mimics endowed with very similar biological
properties but structurally and synthetically simpler than their natural
counterparts. Herein, the synthesis of pseudo-oligosaccharides using
the cross-metathesis reaction between distinct sugar-olefins followed
by intramolecular selenocyclization of the obtained heterodimer as
key steps is first investigated. This methodology has been then applied
to the preparation of structural analogues of the trisaccharide repeating
unit from <i>Streptococcus pneumoniae</i> 19F. The inhibition
abilities of the synthetic molecules were evaluated by a competitive
ELISA assay using a rabbit polyclonal anti-19F serum