Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: a biomimetic model for the H2O2-dependent activity of nitric oxide synthase

Bioorg Med Chem Lett. 2000 Aug 7;10(15):1775-7. doi: 10.1016/s0960-894x(00)00345-0.

Abstract

A chemical model for the H2O2 promoted oxidation by nitric oxide synthase (NOS) has been developed. Biomimetic oxidations were carried out using H2O2 and tetrakis(perfluorophenyl)porphyrinato-iron(III) chloride (FeTPPF20) as a catalyst. Similarly to NOS our model system produces Ndelta-cyanoornithine, citrulline and NO from NOHA and did not oxidize arginine itself. Based on these results we propose a peroxide shunt to be involved in the catalytic cycle of NOS. To the best of our knowledge this is the first chemical system that semiquantitatively mimics NOS activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Guanidines / chemistry*
  • Hydrogen Peroxide / metabolism*
  • Hydroxylamines
  • Metalloporphyrins / chemistry*
  • Models, Chemical
  • Molecular Mimicry
  • Nitric Oxide Synthase / metabolism*
  • Oxidation-Reduction

Substances

  • Guanidines
  • Hydroxylamines
  • Metalloporphyrins
  • hydroxyguanidine
  • Hydrogen Peroxide
  • Nitric Oxide Synthase