Synthesis and HNO Donating Properties of the Piloty's Acid Analogue Trifluoromethanesulphonylhydroxamic Acid: Evidence for Quantitative Release of HNO at Neutral pH Conditions

Sonya K Adas; Vinay Bharadwaj; Yang Zhou; Jiuhong Zhang; Alexander J Seed; Nicola E Brasch; Paul Sampson

doi:10.1002/chem.201800662

Synthesis and HNO Donating Properties of the Piloty's Acid Analogue Trifluoromethanesulphonylhydroxamic Acid: Evidence for Quantitative Release of HNO at Neutral pH Conditions

Chemistry. 2018 May 23;24(29):7330-7334. doi: 10.1002/chem.201800662. Epub 2018 May 9.

Authors

Sonya K Adas¹, Vinay Bharadwaj², Yang Zhou¹, Jiuhong Zhang¹, Alexander J Seed¹, Nicola E Brasch², Paul Sampson¹

Affiliations

¹ Department of Chemistry and Biochemistry, Kent State University, Kent, OH, 44242, USA.
² School of Science, Auckland University of Technology, Private Bag 92006, Auckland, 1142, New Zealand.

PMID: 29527748
DOI: 10.1002/chem.201800662

Abstract

Trifluoromethanesulphonylhydroxamic acid, CF₃ SO₂ NHOH, is shown to release HNO under physiological pH conditions. A two-step synthesis is presented with the first complete characterization of CF₃ SO₂ NHOH. This molecule rapidly decomposes in neutral aqueous solution to cleanly release HNO and CF₃ SO₂^- , which was demonstrated using the HNO traps TXPTS and HOCbl, and by ¹⁹ F NMR spectroscopy.

Keywords: HNO; cobalamins; nitrogen oxides; nitroxyl.