Remarkable activity of a novel cyclic seleninate ester as a glutathione peroxidase mimetic and its facile in situ generation from allyl 3-hydroxypropyl selenide

J Am Chem Soc. 2002 Oct 16;124(41):12104-5. doi: 10.1021/ja028030k.

Abstract

1,2-Oxaselenolane Se-oxide is a novel cyclic seleninate ester that functions as a remarkably efficient glutathione peroxidase mimetic by catalyzing the reduction of tert-butyl hydroperoxide to tert-butyl alcohol in the presence of benzyl thiol. The seleninate ester can be conveniently generated in situ by oxidation of allyl 3-hydroxypropyl selenide with tert-butyl hydroperoxide. Its catalytic activity surpasses that of several other known GPx mimetics containing cyclic selenenamide structures, which were also tested for comparison.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Glutathione Peroxidase / chemistry*
  • Glutathione Peroxidase / metabolism
  • Molecular Mimicry
  • Organoselenium Compounds / chemistry*
  • Organoselenium Compounds / metabolism
  • Selenious Acid / chemistry
  • tert-Butylhydroperoxide / chemistry

Substances

  • Organoselenium Compounds
  • tert-Butylhydroperoxide
  • Glutathione Peroxidase
  • Selenious Acid