{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T09:59:02Z","timestamp":1780394342916,"version":"3.54.1"},"reference-count":33,"publisher":"MDPI AG","issue":"16","license":[{"start":{"date-parts":[[2022,8,19]],"date-time":"2022-08-19T00:00:00Z","timestamp":1660867200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Wake Forest University"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Nitroxyl shows a unique biological profile compared to the gasotransmitters nitric oxide and hydrogen sulfide. Nitroxyl reacts with thiols as an electrophile, and this redox chemistry mediates much of its biological chemistry. This reactivity necessitates the use of donors to study nitroxyl\u2019s chemistry and biology. The preparation and evaluation of a small library of new redox-triggered nitroxyl sources is described. The condensation of sulfonyl chlorides and properly substituted O-benzyl hydroxylamines produced O-benzyl-substituted sulfohydroxamic acid derivatives with a 27\u201379% yield and with good purity. These compounds were designed to produce nitroxyl through a 1, 6 elimination upon oxidation or reduction via a Piloty\u2019s acid derivative. Gas chromatographic headspace analysis of nitrous oxide, the dimerization and dehydration product of nitroxyl, provides evidence for nitroxyl formation. The reduction of derivatives containing nitro and azide groups generated nitrous oxide with a 25\u201392% yield, providing evidence of nitroxyl formation. The oxidation of a boronate-containing derivative produced nitrous oxide with a 23% yield. These results support the proposed mechanism of nitroxyl formation upon reduction\/oxidation via a 1, 6 elimination and Piloty\u2019s acid. These compounds hold promise as tools for understanding nitroxyl\u2019s role in redox biology.<\/jats:p>","DOI":"10.3390\/molecules27165305","type":"journal-article","created":{"date-parts":[[2022,8,21]],"date-time":"2022-08-21T23:51:01Z","timestamp":1661125861000},"page":"5305","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Para-Substituted O-Benzyl Sulfohydroxamic Acid Derivatives as Redox-Triggered Nitroxyl (HNO) Sources"],"prefix":"10.3390","volume":"27","author":[{"given":"Yueming","family":"Long","sequence":"first","affiliation":[{"name":"Department of Chemistry, Wake Forest University, Winston-Salem, NC 27101, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4653-211X","authenticated-orcid":false,"given":"Zijun","family":"Xia","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Wake Forest University, Winston-Salem, NC 27101, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Allison M.","family":"Rice","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Wake Forest University, Winston-Salem, NC 27101, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8647-8026","authenticated-orcid":false,"given":"S. Bruce","family":"King","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Wake Forest University, Winston-Salem, NC 27101, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,8,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1155\/2016\/4627308","article-title":"Gasotransmitters in Biology and Medicine: Molecular Mechanisms and Drug Targets","volume":"2016","author":"Yang","year":"2016","journal-title":"Oxid. Med. Cell. Longev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"215","DOI":"10.1080\/02603598808072309","article-title":"The Aqueous Solution Chemistry of Nitrogen in Low Positive Oxidation States","volume":"7","author":"Bonner","year":"1988","journal-title":"Comments Inorg. 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