[Show abstract][Hide abstract] ABSTRACT: Cyclodextrins (CDs) are cyclic oligosaccharides with a hydrophobic, sizeselective toroidal cavity able to incorporate a large range of hydrophobic molecules. When combined with carbohydrates, they are expected to be exploited as carrier in targeting drug-delivery systems. High-mannose type oligosaccharides (oligomannoses) cover the surface of many pathogenic microorganisms and are implicated in many cell-cell recognition processes such as adhesion and infection. This paper focuses on the synthesis of monosubstituted high-mannosyl b-cyclodextrins. It reports their ability to form complexes with guest molecules and their binding affinity for lectins. Evidence that the use of branched oligomannoses as the recognition motifs is more effective than increasing the valency of the synthetic ligands will be given. To start, the main synthetic strategies available to prepare oligomannose fragments as well as our own work in the field will be described. Finally, we will see that the supramolecular control of oligosaccharide-lectin interactions using logically designed glyco-cyclodextrins is conceivable.
[Show abstract][Hide abstract] 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.
[Show abstract][Hide abstract] ABSTRACT: Bindung oder Nichtbindung: Kohlenhydrat-Protein-Wechselwirkungen lassen sich mithilfe eines gezielt entworfenen β-Cyclodextrin(βCD)-Konjugats, dessen Konformation von einem reversiblen intramolekularen Einschlussprozess abhängt, supramolekular steuern. Der Zugang für Glycoliganden zur Lectin-Bindungsstelle wird dann durch allosterischen Einschluss von Effektoren/Antagonisten im βCD-Hohlraum geregelt (siehe Schema).
[Show abstract][Hide abstract] ABSTRACT: The synthesis of branched beta-cyclodextrins substituted with mannosyl mimetic derivatives at one primary hydroxy group is described. It was shown that the self-inclusion phenomenon observed for the target compounds in water did not preclude the inclusion properties of the cyclodextrin moiety.