Abstract

Based on the design of the fluorescent site of a fluorescent probe, we have created a unique system that changes its twisting response to sugar. Two probes were synthesized, in which phenylboronic acid and two kinds of aromatic fluorescent site (pyrene or anthracene) were conjugated by an amide bond. In the fluorescence measurement of pyrene-type probe 1, dimer fluorescence was observed at high pH. In induced circular dichroism (ICD) experiments, a response was observed only in the presence of glucose and γ-cyclodextrin, and no response was seen with fructose. On the other hand, in the fluorescence measurement of anthracene-type probe 2, dimer fluorescence was observed in the presence of both glucose and galactose, and the fluorescence was different from the case of fructose. When the ICD spectra of these inclusion complexes were measured, an inversion of the Cotton effect, which indicates a change in the twisted structure, was observed in galactose and glucose. These differences in response to monosaccharides may originate in the interaction between the fluorescent site and the cyclodextrin cavity.

中文翻译：

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荧光团对苯硼酸荧光团/环糊精复合物的选择性葡萄糖识别作用

摘要

基于荧光探针荧光位点的设计，我们创建了一个独特的系统，该系统可以改变其对糖的扭曲响应。合成了两个探针，其中苯基硼酸和两种芳香族荧光位点（py或蒽）通过酰胺键结合。在of型探针1的荧光测量中，在高pH下观察到二聚体荧光。在诱导圆二色性（ICD）实验中，仅在葡萄糖和γ-环糊精存在下才观察到反应，而果糖未见反应。另一方面，在蒽型探针2的荧光测定中，在葡萄糖和半乳糖均存在下观察到二聚体荧光，并且该荧光与果糖的情况不同。当测量这些包合物的ICD谱时，在半乳糖和葡萄糖中观察到棉花效应的反转，这表明扭曲结构的改变。这些对单糖反应的差异可能源自荧光部位和环糊精腔之间的相互作用。