ABSTRACT: An original synthetic route based on multi-glycosylation and selective protection–deprotection steps has been developed which
allows a fast access to complex oligomannosides with both α-(1,3),α-(1,6) and α-(1,3),α-(1,4) cores. The later have been linked
to modified β-cyclodextrins bearing spacing arms of varying chemical structure and length through peptidic-like coupling,
leading to the formation of a range of oligomannosyl cyclodextrin conjugates. Complexation studies with sodium anthraquinone-2-sulfonate
(ASANa) and sodium adamantane 1-carboxylate (ACNa) as guest molecules demonstrated that the β-cyclodextrin inclusion properties
are preserved. Binding affinity studies using the mannose specific lectin Concanavalin A (Con A) demonstrated the key role
of the density and tridimensional structure of the sugar ligand in recognition events.
Journal of Inclusion Phenomena 03/2007; 57(1):9-14. · 1.89 Impact Factor