Nitroxyl (HNO) is an important biomolecule whose biological chemistry is challenging to study due to its rapid dimerization. As a result, a variety of HNO donors have been developed as in situ sources of HNO, including several N-hydroxysulfonamides RSO2NHOH (e.g. Piloty’s acid (R=Ph), MSHA (R=Me)). As part of a program aimed at understanding the fundamental bioinorganic chemistry of HNO, we needed to prepare these N-hydroxysulfonamides as well as the new related HNO donor CF3SO2NHOH. Surprisingly, we found that there is a dearth of reliable and efficient approaches for the preparation of these targets. Herein, we will outline improved preparative approaches to these N-hydroxysulfonamide HNO donors. In addition, we will present detailed decomposition kinetics for HNO generation from these compounds, using aquacobalamin to quantify HNO generation.

N-hydroxysulfonamides RSO2NHOH as nitroxyl (HNO) donors: Improved preparation and kinetics of nitroxyl generation

249th National Meeting (2015)

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