Nitric oxide is reduced to HNO by proton-coupled nucleophilic attack by ascorbate, tyrosine, and other alcohols. A new route to HNO in biological media?

Journal of the American Chemical Society
Sebastián A SuárezFabio Doctorovich

Abstract

The role of NO in biology is well established. However, an increasing body of evidence suggests that azanone (HNO), could also be involved in biological processes, some of which are attributed to NO. In this context, one of the most important and yet unanswered questions is whether and how HNO is produced in vivo. A possible route concerns the chemical or enzymatic reduction of NO. In the present work, we have taken advantage of a selective HNO sensing method, to show that NO is reduced to HNO by biologically relevant alcohols with moderate reducing capacity, such as ascorbate or tyrosine. The proposed mechanism involves a nucleophilic attack to NO by the alcohol, coupled to a proton transfer (PCNA: proton-coupled nucleophilic attack) and a subsequent decomposition of the so-produced radical to yield HNO and an alkoxyl radical.

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Citations

Feb 3, 2016·Journal of the American Chemical Society·Sunghee KimStephen J Lippard
Aug 19, 2015·Inorganic Chemistry·Mariana HamerFabio Doctorovich
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Sep 20, 2017·Journal of the American Chemical Society·Sebastian A SuarezFabio Doctorovich
Aug 28, 2021·Chemical Science·Cecilia Mariel GallegoFabio Doctorovich
Nov 20, 2021·Inorganic Chemistry·Rakesh MazumdarBiplab Mondal

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