Reactive oxygen species (ROS) such as hydrogen peroxide (HO) and peroxynitrite (ONOO) oxidize arylboronic acids to their corresponding phenols. When used in molecular imaging probes and in ROS-responsive molecules, however, simple arylboronic acids struggle to discriminate between HO and ONOO because of their fast rate of reaction with both ROS. Here, we show that diazaborines (DABs) react slowly with HO but rapidly with peroxynitrite in an aqueous buffer. In addition to their slow reaction with HO, the immediate product of DAB oxidation with HO and ONOO can yield a kinetically trapped CN -isomer that slowly equilibrates with its -isomer. Taken together, our work shows that diazaborines exhibit enhanced kinetic discrimination between HO and ONOO compared to arylboronic acids, opening up new opportunities for diazaborine-based tools in chemical biology.
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