Supramolecular carbohydrate-based hydrogels from oxidative hydroxylation of amphiphilic β-C-glycosylbarbiturates and α-glucosidase-induced hydrogelation - Archive ouverte HAL Access content directly
Journal Articles Green Chemistry Year : 2022

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

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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.
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hal-03920384 , version 1 (03-01-2023)

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Shun Yao, Robin Brahmi, Anaïs Bouschon, Jing Chen, Sami Halila. Supramolecular carbohydrate-based hydrogels from oxidative hydroxylation of amphiphilic β-C-glycosylbarbiturates and α-glucosidase-induced hydrogelation. Green Chemistry, 2022, 25 (1), pp.330-335. ⟨10.1039/D2GC04180D⟩. ⟨hal-03920384⟩
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