Chemical Sensing of Polyols with Shapeshifting Boronic Acids As a Self-Contained Sensor Array

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• 作者：Johannes F. Teichert ; Dmitry Mazunin ; Jeffrey W. Bode
• 刊名：The Journal of the American Chemical Society
• 出版年：2013
• 出版时间：July 31, 2013
• 年：2013
• 卷：135
• 期：30
• 页码：11314-11321
• 全文大小：578K
• 年卷期：v.135,no.30(July 31, 2013)
• ISSN：1520-5126

文摘

Boronic acid-substituted shapeshifting bullvalenes bearing a ¹³C label are employed as sensor arrays for polyhydroxylated compounds, such as carbohydrates, flavanols, and sialic acids. The dynamic nature of the bullvalene core allows for covalent binding to a wide variety of analytes, allowing for specific analyte detection by a single NMR measurement. The resulting ¹³C NMR patterns permit an inference to the identity of a particular analyte bound. Conversion of the ¹³C NMR to an easy-to-read barcode provides a convenient method to catalog polyol analytes. The synthesis and study of a structurally related static sensor, which is not suitable for analyte recognition, underscores the advantages of the shapeshifting nature of the sensor.