Synthèse et caractérisation de cyclodextrines mannosylées

AMIENS-BU Sciences (800212103) / SudocSudocFranceF

Oligosaccharide tagged β-cyclodextrins: synthesis and biological affinity towards Concanavalin A

6 páginas, 2 figuras, 5 esquemas.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.This work was supported by the Conseil Régional de Picardie under the scientific IBFBio program.Peer reviewe

Oligosaccharide tagged β-cyclodextrins: synthesis and biological affinity towards Concanavalin A

6 páginas, 2 figuras, 5 esquemas.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.This work was supported by the Conseil Régional de Picardie under the scientific IBFBio program.Peer reviewe

Supramolecular Control of Oligosaccharide–Protein Interactions: Switchable and Tunable Ligands for Concanavalin A Based on β-Cyclodextrin

4 páginas, figurasThe ins and outs of binding: Supramolecular control of carbohydrate–protein interactions has been achieved through the design of β-cyclodextrin (βCD) based conjugates whose conformation is dependent on a reversible self-inclusion process. The accessibility of glycoligands to the lectin binding site is then regulated by allosteric inclusion of effector/antagonist-like molecules in the βCD cavity (see scheme).This work was supported by the Conseil Régional de Picardie under the scientific IBFBio program and by the Spanish Ministerio de Educación y Ciencia (contract number BQU2003-00937). D.Y. is grateful to the Ministère Gabonais des Finances et des Bourses et Stages for a doctoral fellowship. N.S. is grateful to the Conseil Régional de Picardie for a doctoral fellowship.Peer reviewe