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

2013; American Chemical Society; Volume: 135; Issue: 30 Linguagem: Inglês

10.1021/ja404981q

1943-2984

Johannes F. Teichert, Dmitry Mazunin, Jeffrey W. Bode,

Advanced Chemical Sensor Technologies

Boronic acid-substituted shapeshifting bullvalenes bearing a (13)C 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 (13)C NMR patterns permit an inference to the identity of a particular analyte bound. Conversion of the (13)C 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.