The Sulfenic Acids and their Derivatives.

Kharasch, Norman; Potempa, Sylvester J.; Wehrmeister, H. L.

doi:10.1021/cr60123a004

Cited by 153 publications

(35 citation statements)

References 64 publications

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“…3, reaction 3), hydrazine and alkyl hydrazines (Fig. 3, reaction 6) and sodium azide can reduce RSOH back to the thiol [23,24]. Although the abovementioned reactions span across several classes, they can be categorized as and attributed to the electrophilic character of sulfur atom in sulfenic acid.…”

Section: The Chemistry Of Sulfenic Acidmentioning

confidence: 99%

Sulfenic acid chemistry, detection and cellular lifetime

Gupta

Carroll

2014

Biochimica et Biophysica Acta (BBA) - General Subjects

377

399

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Background Reactive oxygen species-mediated cysteine sulfenic acid modification has emerged as an important regulatory mechanism in cell signaling. The stability of sulfenic acid in proteins is dictated by the local microenvironment and ability of antioxidants to reduce this modification. Several techniques for detecting this cysteine modification have been developed, including direct and in situ methods. Scope of review This review presents a historical discussion of sulfenic acid chemistry and highlights key examples of this modification in proteins. A comprehensive survey of available detection techniques with advantages and limitations is discussed. Finally, issues pertaining to rates of sulfenic acid formation, reduction, and chemical trapping methods are also covered. Major conclusions Early chemical models of sulfenic acid yielded important insights into the unique reactivity of this species. Subsequent pioneering studies led to the characterization of sulfenic acid formation in proteins. In parallel, the discovery of oxidant-mediated cell signaling pathways and pathological oxidative stress has led to significant interest in methods to detect these modifications. Advanced methods allow for direct chemical trapping of protein sulfenic acids directly in cells and tissues. At the same time, many sulfenic acids are short-lived and the reactivity of current probes must be improved to sample these species, while at the same time, preserving their chemical selectivity. Inhibitors with binding scaffolds can be rationally designed to target sulfenic acid modifications in specific proteins. General significance Ever increasing roles for protein sulfenic acids have been uncovered in physiology and pathology. A more complete understanding of sulfenic acid-mediated regulatory mechanisms will continue to require rigorous and new chemical insights. This article is part of a Special Issue entitled Current methods to study reactive oxygen species - pros and cons and biophysics of membrane proteins. Guest Editor: Christine Winterbourn.

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Section: The Chemistry Of Sulfenic Acidmentioning

confidence: 99%

Sulfenic acid chemistry, detection and cellular lifetime

Gupta

Carroll

2014

Biochimica et Biophysica Acta (BBA) - General Subjects

377

399

View full text Add to dashboard Cite

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“…Excess amount of chlorine leads to the formation of polychlorides RSCl 2 SCl 2 R and RSCl 3 [19], which are unstable and pollute sulfenylchlorides. The reaction is carried out in anhydrous chloroform or carbon tetrachloride.…”

Section: Synthesis Of the Sulfenylchlorides Of 14-naphthoquinonementioning

confidence: 99%