A chiral BINOL-based supramolecular gel enabling sensitive enantioselective and chemoselective collapse toward histidine,Soft Matter

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A chiral BINOL-based supramolecular gel enabling sensitive enantioselective and chemoselective collapse toward histidine
Soft Matter ( IF 2.9 ) Pub Date : 2022-12-08 , DOI: 10.1039/d2sm01424f
Yixuan Jiang ₁ , Zeng Huang ₂ , Jun Tian ₁ , Xin Dong ₁ , Xiao-Qi Yu _{1,

3} , Shanshan Yu ₁

Affiliation

A chiral small molecule gelator (R)-H₃L based on 1,1′-bi-2,2′-naphthol (BINOL)-phosphoric acid was designed and prepared, which spontaneously forms a stable water-induced gel. The gelation mechanism was revealed by single crystal X-ray diffraction analysis and a number of spectroscopic methods. Addition of Cu²⁺ improved the gelation ability, and the resultant metal organic gel realized visual enantioselective and chemoselective recognition toward L-histidine from enantiomers of 19 amino acids via gel collapse. The gel showed a highly sensitive response to L-histidine, and as low as 0.01 equiv. of L-histidine relative to the critical gelation concentration of (R)-H₃L-Cu caused the gel to collapse. This strategy of regulating the assembly behavior through the interaction of amino acids and metal ions not only provides a simple and direct way to distinguish enantiomers, but also provides insight into how metal ions regulate the organization of biological supramolecular systems.

中文翻译：

一种基于 BINOL 的手性超分子凝胶，可实现对组氨酸敏感的对映选择性和化学选择性塌陷

设计并制备了一种基于1,1'-双-2,2'-萘酚(BINOL)-磷酸的手性小分子胶凝剂( R )-H _{3 L，该胶凝剂可自发形成稳定的水诱导凝胶。}通过单晶 X 射线衍射分析和多种光谱方法揭示了凝胶化机理。Cu ²⁺的加入提高了胶凝能力，所得金属有机凝胶通过凝胶塌陷实现了对19个氨基酸对映体中L-组氨酸的视觉对映选择性和化学选择性识别。该凝胶对L-组氨酸显示出高度敏感的反应，低至 0.01 当量。的_-组氨酸相对于( R )-H ₃ L-Cu的临界胶凝浓度导致凝胶塌陷。这种通过氨基酸和金属离子的相互作用调节组装行为的策略不仅提供了一种简单直接的方法来区分对映异构体，而且还提供了金属离子如何调节生物超分子系统组织的见解。

更新日期：2022-12-08

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