Effects of Methoxy Substituents on the Glutathione Peroxidase-like Activity of Cyclic Seleninate Esters

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...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-10, Vol.79 (19), p.9394-9401
Main Authors: Press, David J, McNeil, Nicole M. R, Hambrook, Miranda, Back, Thomas G
Format: Article
Language:English
Subjects:
Antioxidants - chemistry
Catalysis
Esters
Glutathione Peroxidase - chemistry
Glutathione Peroxidase - metabolism
Hydrogen Peroxide - chemistry
Molecular Mimicry
Organoselenium Compounds - chemistry
Sulfhydryl Compounds - chemistry
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501689h