Boronic acid-appended bipyridinium salts are well known receptors for sensing carbohydrates via fluorescence spectroscopy. 1-4 Compared to fluorescence - 19F NMR spectroscopy, particularly used for sensing biological events, is currently growing to be a valuable tool.5 For instance, nearly no disturbing background signals are present and characteristic and easy to readout 19F NMR shifts can be recorded due to the high environmental sensitivity of the fluorine probe without the need of e.g. an external reporting molecule. Herein, we demonstrate a new sensing concept for diol-containing analytes in water via fluorinated boronic acid-appended pyridinium salts and 19F NMR spectroscopy. 19F NMR fingerprints are produced by the remarkable sensitivity of the 19F probe which recognizes bound analytes at the boronic acid binding site. With this property in hand, we used an array of three water-soluble boronic acid receptors in combination with 19F NMR spectroscopy to discriminate diol-containing bioanalytes such as D-fructose, -glucose, -glucose-6-phosphate, -galactose and catechol derivatives at low mM concentrations.6 Highly characteristic 19F NMR fingerprints can be interpreted as two-dimensional barcodes without the need of multivariate analysis techniques. The power of this method is a clear and unambiguous detection and quantification of diol-containing analytes. In addition, our approach was furthermore successfully applied in monitoring diol in complex media and enzyme catalyzed reactions.

Fluorinated boronic acid-appended pyridinium salts for Diol recognition & discrimination in water using 19F NMR

253rd National Meeting (2017)

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