Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate-protein...

Area of Science:

• Carbohydrate Chemistry
• Supramolecular Chemistry
• Bioconjugation Chemistry

Background:

• Cyclodextrins (CDs) are versatile macrocycles amenable to precise functionalization.
• Multivalent carbohydrate ligands (glycotopes) are essential for understanding biological recognition events.
• Developing homogeneous and well-defined glycoconjugates is critical for reliable studies.

Purpose of the Study:

• To explore the covalent attachment of biorecognizable sugar ligands to cyclodextrins.
• To create precisely controlled multivalent glycoconjugates with defined valency and spatial orientation.
• To investigate the utility of these glycoconjugates in deciphering carbohydrate recognition and developing new applications.

Main Methods:

• Utilizing commercially available cyclodextrins (CDs) with varying sizes.
• Employing "click-type" ligation chemistries (e.g., CuAAC, thiol-ene) for homogeneous adduct formation.
• Functionalizing CDs at specific positions and faces to control glycotopes' orientation and valency.

Main Results:

• Successful synthesis of homogeneous multivalent CD conjugates with controlled valency and spatial arrangement of glycotopes.
• Demonstrated ability to incorporate diverse glycotopes for studying heterogeneous interactions.
• Development of nanometric glycoassemblies with adaptable structures and functions.

Conclusions:

• Multivalent CD conjugates are powerful tools for fundamental studies in carbohydrate recognition.
• These advanced glycoconjugates show significant promise for applications in sensors, drug/gene delivery, and protein stabilization.
• The strategy offers a flexible platform for designing sophisticated glycomaterials.