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Updated: Jun 16, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Small molecular, macromolecular, and cellular chloramines react with thiocyanate to give the human defense factor
Bheki A Xulu1, Michael T Ashby
1Department of Chemistry and Biochemistry, University of Oklahoma, Norman, Oklahoma 73019, USA.
Abstract:
Thiocyanate reacts noncatalytically with myeloperoxidase-derived HOCl to produce hypothiocyanite (OSCN(-)), thereby potentially limiting the propensity of HOCl to inflict host tissue damage that can lead to inflammatory diseases. However, the efficiency with which SCN(-) captures HOCl in vivo depends on the concentration of SCN(-) relative to other chemical targets. In blood plasma, where the concentration of SCN(-) is relatively low, proteins may be the principal initial targets of HOCl, and chloramines are a significant product. Chloramines eventually decompose to irreversibly damage proteins. In the present study, we demonstrate that SCN(-) reacts efficiently with chloramines in small molecules, in proteins, and in Escherichia coli cells to give OSCN(-) and the parent amine. Remarkably, OSCN(-) reacts faster than SCN(-) with chloramines. These reactions of SCN(-) and OSCN(-) with chloramines may repair some of the damage that is inflicted on protein amines by HOCl. Our observations are further evidence for the importance of secondary reactions during the redox cascades that are associated with oxidative stress by hypohalous acids.
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