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- Title
Hierarchical Self‐Assembly of Amphiphilic β‐C‐Glycosylbarbiturates into Multiresponsive Alginate‐Like Supramolecular Hydrogel Fibers and Vesicle Hydrogel.
- Authors
Yao, Shun; Brahmi, Robin; Portier, François; Putaux, Jean‐Luc; Chen, Jing; Halila, Sami
- Abstract
Ordered molecular self‐assembly of glycoamphiphiles has been regarded as an attractive, practical and bottom‐up approach to obtain stable, structurally well‐defined, and functional mimics of natural polysaccharides. This study describes a versatile and rational design of carbohydrate‐based hydrogelators through N,N'‐substituted barbituric acid‐mediated Knoevenagel condensation onto unprotected carbohydrates in water. Amphiphilic N‐substituted β‐C‐maltosylbarbiturates self‐assembled into pH‐ and calcium‐triggered alginate‐like supramolecular hydrogel fibers with a multistimuli responsiveness to temperature, pH and competitive metal chelating agent. In addition, amphiphilic N,N'‐disubstituted β‐C‐maltosylbarbiturates formed vesicle gels in pure water that were scarcely observed for glyco‐hydrogelators. Finally, barbituric acid worked as a multitasking group allowing chemoselective ligation onto reducing‐end carbohydrates, structural diversity, stimuli‐sensitiveness, and supramolecular interactions by hydrogen bonding.
- Subjects
MOLECULAR self-assembly; FIBERS; HYDROGEN bonding interactions; CHELATING agents; BIOMIMETIC materials
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 67, p16716
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202102950