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

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