A highly fluorescent water-soluble boronic acid reporter for saccharide sensing that shows ratiometric UV changes and significant fluorescence changes |
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Authors: | Xingming Gao |
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Institution: | Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, GA 30302-4089, USA |
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Abstract: | One water-soluble naphthalene-based fluorescent boronic acid, 6-(dimethylamino)-naphthalene-2-boronic acid (6-DMANBA, 1), has been synthesized. 6-DMANBA shows significant ratiometric UV absorbance changes upon addition of a sugar. For example, addition of 50 mM fructose shifted the UV absorption wavelengths of 6-DMANBA from 306 and 251 to 280 and 244 nm, respectively. In addition, 6-DMANBA is highly fluorescent with a quantum yield of 89% in the absence of a sugar and shows significant fluorescence intensity changes with the addition of a saccharide in aqueous phosphate buffer at physiological pH. For example, with the addition of 50 mM fructose, 6-DMANBA shows an 80% fluorescent intensity decrease at 432 nm. All these spectroscopic properties make compound 1 unique and useful. |
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Keywords: | Boronic acid Fluorescent sensor Carbohydrate Ratiometric UV Boronolectin |
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