title: Effects of methoxy substituents on the glutathione peroxidase-like activity of cyclic seleninate esters.
abstract: Cyclic seleninate esters function as mimetics of the antioxidant enzyme glutathione peroxidase and catalyze the reduction of hydrogen peroxide with a stoichiometric thiol. While a single electron-donating methoxy substituent para to the selenium atom enhances the catalytic activity, m-methoxy groups have little effect and o-methoxy substituents suppress activity. The effects of multiple methoxy groups are not cumulative. This behavior can be rationalized by opposing mesomeric and steric effects. Oxidation of the product disulfide via its thiolsulfinate was also observed.
authors.affiliation: Department of Chemistry, University of Calgary , 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4.
authors.forename: David J
authors.initials: DJ
authors.lastname: Press
authors.forename: Nicole M R
authors.initials: NM
authors.lastname: McNeil
authors.forename: Miranda
authors.initials: M
authors.lastname: Hambrook
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Back
mesh_terms: D000975:Antioxidants / Q000737:chemistry*; D002384:Catalysis; D004952:Esters; D005979:Glutathione Peroxidase / Q000737:chemistry* / Q000378:metabolism; D006861:Hydrogen Peroxide / Q000737:chemistry*; D018716:Molecular Mimicry; D016566:Organoselenium Compounds / Q000737:chemistry*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
chemical_list: D000975:Antioxidants; D004952:Esters; D016566:Organoselenium Compounds; D013438:Sulfhydryl Compounds; D006861:Hydrogen Peroxide; D005979:Glutathione Peroxidase