Remarkable activity of a novel cyclic seleninate ester as a glutathione peroxidase mimetic and its facile in situ generation from allyl 3-hydroxypropyl selenide.
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.
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Thomas G
TG
Department of Chemistry, University of Calgary, Calgary, Alberta, Canada T2N 1N4.
Moussa
Ziad
Z
D002384:Catalysis; D005979:Glutathione Peroxidase / Q000737:chemistry* / Q000378:metabolism; D018716:Molecular Mimicry; D016566:Organoselenium Compounds / Q000737:chemistry* / Q000378:metabolism; D020887:Selenious Acid / Q000737:chemistry; D020122:tert-Butylhydroperoxide / Q000737:chemistry
D016566:Organoselenium Compounds; D020122:tert-Butylhydroperoxide; D005979:Glutathione Peroxidase; D020887:Selenious Acid