Department of Chemistry, University of South Florida, 4202 E. Fowler Ave, Tampa, FL, 33620, USA.
Chemistry. 2023 Jun 7;29(32):e202300524. doi: 10.1002/chem.202300524. Epub 2023 Apr 25.
A biomimetic receptor for glucose has been developed with high affinity and selectivity. The receptor was efficiently synthesized in three steps through dynamic imine chemistry followed by imine-to-amide oxidation. The receptor features two parallel durene panels, forming a hydrophobic pocket for [CH⋅⋅⋅π] interactions, and two pyridinium residues directing four amide bonds towards the pocket. These pyridinium residues not only improve solubility but also provide polarized C-H bonds for hydrogen bonding. Experimental data and DFT calculations show that these polarized C-H bonds significantly enhance substrate binding. These findings demonstrate the power of dynamic covalent chemistry for creating molecular receptors and using polarized C-H bonds for boosted carbohydrate recognition in water, providing a foundation for developing glucose-responsive materials and sensors.
已经开发出一种具有高亲和力和选择性的葡萄糖仿生受体。该受体通过动态亚胺化学和随后的亚胺到酰胺氧化，高效地在三步内合成。该受体具有两个平行的蒽环面板，形成用于[CH⋅⋅⋅π]相互作用的疏水性口袋，以及两个吡啶基残基将四个酰胺键引导到口袋中。这些吡啶基残基不仅提高了溶解度，还为氢键提供了极化的 C-H 键。实验数据和 DFT 计算表明，这些极化的 C-H 键显著增强了底物结合。这些发现证明了动态共价化学在创建分子受体以及在水中使用极化的 C-H 键增强碳水化合物识别方面的强大功能，为开发葡萄糖响应材料和传感器提供了基础。
