A new fluorescent chemical sensor for glucosamine, based on a boronic ester-contaning coumarin aldehyde is reported. The sensor successfully discriminates glucosamine from many other similar amine and diol containing biomolecules in terms of both fluorescence intensity emitted and binding constant. The suitable geometrical arrangement of multi functional groups of the sensor dramatically enhances the selectivity in high salt physiological conditions. The sensor shows excellent selectivity for D-glucosamine with an emission red shift by forming a boronic ester with a sugar diol as well as forming an iminium ion with the amine group of D-glucosamine. We believe that this probe will be a great benefit to ongoing research on the pharmacological effects of D-glucosamine. In addition, the strategy behind this sensor may inspire research toward sensitive and selective fluorescent sensors for complicated biomolecules.

Highly selective fluorescent sensor for D-glucosamine

248th National Meeting (2014)

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