Capturing a Sulfenic Acid with Arylboronic Acids and
Benzoxaborole
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Abstract
Post-translational redox generation
of cysteine-sulfenic acids
(Cys-SOH) functions as an important reversible regulatory mechanism
for many biological functions, such as signal transduction, balancing
cellular redox states, catalysis, and gene transcription. Herein we
show that arylboronic acids and cyclic benzoxaboroles can form adducts
with sulfenic acids in aqueous medium and that these boron-based compounds
can potentially be used to trap biologically significant sulfenic
acids. As proof of principle we demonstrate that a benzoxaborole can
inhibit the enzyme activity of an iron-containing nitrile hydratase,
which requires a catalytic αCys114-SOH in the active site. The
nature of the adduct and the effect of the boronic acid’s p<i>K</i><sub>a</sub><sup>B</sup> on the stability constant of the
adduct are discussed within