Copper-Catalyzed Tyrosine Nitration.

Tyrosine nitration, often observed during neurodegenerative disorders under nitrative stress, is usually considered to be induced chemically either by nitric oxide and oxygen forming nitrogen dioxide or by the decomposition of peroxynitrite. It can also be induced enzymatically by peroxidases or sup...

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Publicado en:Journal of the American Chemical Society Vol. 133; no. 49; pp. 19823 - 19832
Autores principales: Liang Qiao, Yu Lu, Baohong Liu, Hubert H. Girault
Formato: Artículo
Publicado: American Chemical Society 12/14/2011
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Acceso en línea:Ver este registro en EBSCOhost
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      dt: 12/14/2011
      vid: 133
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      pub: American Chemical Society
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        10.1021/ja206980q
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      tig:
        atl: Copper-Catalyzed Tyrosine Nitration.
      aug:
        au:
          Liang Qiao
          Yu Lu
          Baohong Liu
          Hubert H. Girault
        affil:
          Laboratoire d'Electrochimie Physique et Analytique, Ecole Polytechnique Fédérale de Lausanne, Station 6, CH-1015 Lausanne, Switzerland
          Department of Chemistry, Institute of Biomedical Sciences, Fudan University, Shanghai 200433, People's Republic of China
      su:
        Nitration
        Tyrosine
        Copper catalysts
        Neurodegeneration
        Biomolecules
        Reactive nitrogen species
      sug:
        subj:
          Nitration
          Tyrosine
          Copper catalysts
          Neurodegeneration
          Biomolecules
          Reactive nitrogen species
      ab: Tyrosine nitration, often observed during neurodegenerative disorders under nitrative stress, is usually considered to be induced chemically either by nitric oxide and oxygen forming nitrogen dioxide or by the decomposition of peroxynitrite. It can also be induced enzymatically by peroxidases or superoxide dismutases in the presence of both hydrogen peroxide and nitrite forming nitrogen dioxide and/or peroxynitrite. In this study, the role of cupric ions for catalyzing tyrosine nitration in the presence of hydrogen peroxide and nitrite, by a chemical mechanism rather similar to enzymatic pathways where nitrite is oxidized to form nitrogen dioxide, was investigated by development of a microreactor also capable of acting as an emitter for electrospray ionization mass spectrometry analysis. Indeed, cupric ions and peptide-cupric ion complexes are found to be excellent Fenton catalysts, even better than Fe(III) or heme, for the formation of ·OH radicals and/or copper(II)-bound ·OH radicals from hydrogen peroxide. These radicals are efficiently scavenged by nitrite anions to form ·NO and by tyrosine to form tyrosine radicals, leading to tyrosine nitration in polypeptides. We also show that cupric ions can catalyze tyrosine nitration from nitric oxide, oxygen, and hydrogen peroxide as the formation of tyrosine radicals is increased in the presence of diffusible and/or copper(II) bound hydroxyl radicals. This study shows that copper has a polyvalent role in the processes of tyrosine nitration.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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