One-Pot Multicomponent Synthesis of Glycopolymers through a Combination of Host–Guest Interaction, Thiol-ene, and Copper-Catalyzed Click Reaction in Water

5 years ago

One-Pot Multicomponent Synthesis of Glycopolymers through a Combination of Host–Guest Interaction, Thiol-ene, and Copper-Catalyzed Click Reaction in Water

Gaojian Chen, Yishi Dong, Ting Wei, Xiang Hu, Jinbo Gao, Hong Chen, Yan Luo

There is a common phenomenon that the heterogeneity of natural oligosaccharides contains various sugar units, which can be used to enhance affinity and selectivity toward a specific receptor, so the synthesis of heterogeneous glycopolymers is always an important issue in the glycopolymer field. Herein, this study conducts a one-pot method to prepare polyrotaxane-based heteroglycopolymers anchored with different sugar units and fluorescent moieties via the combination of host–guest interaction, thiol-ene, and copper-catalyzed click chemistry in water. Fourier transform infrared spectroscopy, nuclear magnetic resonance spectroscopy, gel permeation chromatography, X-ray diffraction, and Ellman's assay test are used in the paper to characterize the compounds. Quartz crystal microbalance-dissipation (QCD-D) experiments and bacterial adhesion assay are utilized to study the interactions of polyrotaxane-based heteroglycopolymers with Con A and Escherichia coli. The results reveal that polyrotaxanes (PRs) with mannose and glucose present better specificity toward Con A and E. coli than PRs with glucose due to synergistic effects. Polyrotaxane (PR)-based heteroglycopolymers, armored with different sugar and fluorescent moieties, is prepared through a one-pot method with the combination of host–guest interaction, thiol-ene, and copper-catalyzed click chemistry in water, and the glycopolymers present good lectin and bacteria binding abilities.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/marc.201700434