Substituent effects upon the catalytic activity of aromatic cyclic seleninate esters and spirodioxyselenuranes that act as glutathione peroxidase mimetics.
Substituent effects were studied in a series of aromatic cyclic seleninate esters and spirodioxyselenuranes that function as mimetics of the antioxidant selenoenzyme glutathione peroxidase. The methoxy-substituted selenurane proved the most efficacious catalyst for the reduction of hydrogen peroxide with benzyl thiol, and the reaction rates were enhanced for both classes by electron-donating substituents. Hammett plots indicated rho = -0.45 and -3.1 for the seleninates and selenuranes, respectively, suggesting that oxidation at Se is the rate-determining step in their catalytic cycles.
Press
David J
DJ
Department of Chemistry, University of Calgary, Calgary, Alberta, Canada.
Mercier
Eric A
EA
Kuzma
Dusan
D
Back
Thomas G
TG
D002384:Catalysis; D003500:Cyclization; D004952:Esters; D005979:Glutathione Peroxidase / Q000737:chemistry*; D018716:Molecular Mimicry; D012643:Selenium / Q000737:chemistry*
D004952:Esters; D005979:Glutathione Peroxidase; D012643:Selenium