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Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO).

Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO). Research Abstract Details 

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  • Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO). Abstract Text:

    xin shaXin Sha,t scott isbellT Scott Isbell,rakesh p patelRakesh P Patel,cynthia s dayCynthia S Day,s bruce kingS Bruce King,

    Nitroxyl (HNO/NO(-)), the reduced form of nitric oxide, has gained attention based on its separate chemistry and biology from nitric oxide. The inherent reactivity of HNO requires new and mechanistically unique donors for the detailed study of HNO chemistry and biology. Oxidation of cyclohexanone oxime with lead tetraacetate yields 1-nitrosocyclohexyl acetate, whereas oxidation of oximes in the presence of excess carboxylic acid gives various acyloxy nitroso compounds. These bright blue compounds exist as monomers as indicated by their infrared, proton, and carbon NMR spectra, and X-ray crystallographic analysis reveals the nitroso groups possess a "nitroxyl-like" bent configuration. Hydrolysis of these compounds produces nitrous oxide, the dimerization and dehydration product of HNO, and provides evidence for the intermediacy of HNO. Both thiols and oxidative metal complexes inhibit nitrous oxide formation. Hydrolysis of these compounds in the presence of ferric heme complexes forms ferrous nitrosyl complexes providing further evidence for the intermediacy of HNO. Kinetic analysis shows that the rate of hydrolysis depends on pH and the structure of the acyl group of the acyloxy nitroso compound. These compounds relax pre-constricted rat aortic rings similar to known HNO donors. Together, these results identify acyloxy nitroso compounds as a new class of HNO donors.

    Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO). Publishing Authors By Initials

    x shaX Sha,ts isbellTS Isbell,rp patelRP Patel,cs dayCS Day,sb kingSB King,

    For similar abstracts research abstracts see: abstracts research

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    Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO). Journal Published:

    PUBLICATION TYPE: Research Support, U.S. Gov't,

    Journal: Journal of the American Chemical Society

    VOLUME: 128

    Page Numbers: 9687-92

    Journal Abbreviation:

    ISSN: 0002-7863

    DAY: 2

    MONTH: Aug

    YEAR: 2006

    Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO). Information

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    LANGUAGE: eng

    NlmUniqueID: 7503056

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    Grant and Affiliation Information for Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO).

    AFFILIATION: Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109, USA.

    Country: United States

    United States Research PublicationUnited States Research Publication

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    MEDLINETA: J Am Chem Soc

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