Supramolecular carbohydrate-based hydrogels from oxidative hydroxylation of amphiphilic β-C-glycosylbarbiturates and α-glucosidaseinduced hydrogelation

20 January 2023
The team "Self-assembly of Glycopolymers" of CERMAV has developed a new family of sugar derivatives through an eco-responsible process which is able to self-assemble into hierarchical glyconanostructures to ultimately gel water and the gelation can be triggered by the action of a glycosidase. Click on the title for more information.

Abstract:

“We describe an ecofriendly two-step synthesis of glycoamphiphiles, capable of hierarchical self-assembly into supramolecular hydrogels, consisting of Knoevenagel condensation of barbituric acid derivatives with biobased carbohydrates (glucose and maltose) and selective H2O2-mediated oxidative hydroxylation of barbiturates in water. By modifying the molecular design of glycostructures and the hydrophilic/hydrophobic balance, various glyco-nanostructures (ribbons, tapes, vesicles, helices, fibers) have been created via supramolecular self-assembly. In addition, we found that a water-soluble glycoamphiphile underwent sol-to-gel phase transition upon the addition of α-glucosidase as a result of the hydrolysis of the non-reducing-end glucose in the maltose moiety”

The article is available on the Editor’s website over here and in HAL (open access) over here.