CHIRAL DISCRIMINATION OF MONOSACCHARIDES USING A FLUORESCENT MOLECULAR SENSOR
CHIRAL DISCRIMINATION OF MONOSACCHARIDES USING A FLUORESCENT MOLECULAR SENSOR
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DOI：
10.1038/374345a0
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发表时间：
1995-03-23
期刊：
影响因子：
64.8
通讯作者：
SHINKAI, S
中科院分区：
文献类型：
--
作者：
JAMES, TD;SANDANAYAKE, KRAS;SHINKAI, S
区分手性分子对映体的方法在分析化学和生物技术的许多领域，特别是在药物设计和合成中至关重要。特别是，能够手性识别的基于溶液的传感器系统将具有巨大的制药价值。在这里，我们报告的手性歧视的D-和L-单糖使用设计的受体分子，作为传感器凭借其荧光响应结合的客体物种。我们的受体含有硼酸基团，通过共价相互作用与客体结合;这种受体系统以前已经被大量研究（1 - 6）用于客体的络合，并且比基于氢键相互作用的其他受体系统具有优势（7 - 11），其中极性质子溶剂如水可以与客体结合竞争。我们的分子传感器还结合了荧光萘基部分;单糖的每个对映体的结合在不同程度上改变了荧光强度，使它们能够被区分开。这些水溶性的分子传感器可能形成的基础上，定量和选择性的分析方法，为细菌。
MEANS of distinguishing between enantiomers of a chiral molecule are of critical importance in many areas of analytical chemistry and biotechnology, particularly in drug design and synthesis. In particular, solution-based sensor systems capable of chiral recognition would be of tremendous pharmaceutical value. Here we report the chiral discrimination of D- and L-monosaccharides using a designed receptor molecule that acts as a sensor by virtue of its fluorescent response to binding of the guest species. Our receptor contains boronic acid groups that bind saccharides by covalent interactions; such receptor systems have been much studied previously(1-6) for complexation of saccharides, and have an advantage over others based on hydrogen-bonding interactions(7-11), for which polar protic solvents such as water can compete with guest binding. Our molecular sensor also incorporates a fluorescent naphthyl moiety; binding of each enantiomer of the monosaccharides alters the fluorescence intensity to differing degrees, enabling them to be distinguished. These water-soluble molecular sensors might form the basis of a quantitative and selective analytical method for saccharides.