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A new bisboronic acid based glucose sensor 7 was synthesized from 9,10-bis(chloromethyl)anthracene and 2,2-dimethyl-1,3-propanediol protected 3-pyridineboronic acid. Due to its ionic structure 7 was found sufficiently water soluble for carbohydrate binding studies at neutral pH by means of NMR spectroscopy, fluorometry, and potentiometry. The p K a 's of 7 have been determined to 3.7 and 4.7 by potentiometric titration. From a solution of 7 and glucose (1:1) in water (pH 7.4) we observed the formation of a bisdentate boronic acid complex 7·Glu which has been assigned to a 1,2:3,5 bound α- d -glucofuranose complex. The evidence for this furanose structure comprises 1 H and 13 C NMR data with emphasis on the information from 1 J C - C coupling constants. Complex 7·Glu shows an increased fluorescence compared to 7 . The stability constant for the 1:1 complex (log K = 3.4) was determined from fluorometric titration, potentiometry, and NMR spectroscopy. Boronic acid 7 shows good selectivity for glucose compared to fructose and galactose.
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Eggert et al. (1999) studied this question.
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