Abstract
In our continuing efforts into designing boronic acid-based sensors that recognize cell-surface carbohydrates, it has been necessary to examine various factors that affect the binding affinity between a boronic acid moiety and a diol. The current prevailing view is that the strongest boronic acid/diol complexes are generated by a combination of high solution pH and a low boronic acid pK a. However, there has never been a systematic examination of the relationship among the binding constants, boronic acid pK a, and the pH of the solution. Herein we report our findings with a series of 25 arylboronic acids with various substituents and their binding affinities with diols. We have found that (1) the relationship between the pK a of monosubstituted phenylboronic acid and its substituents can be described using a Hammet plot; (2) the optimal pH for binding is not always above the pK a of the boronic acid, and is affected by the pK a values of the boronic acid and the diol, and other unknown factors; and (3) the general belief that boronic acids with lower pK a values show greater binding affinities for diols is not always true.
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