Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 79, Issue 19, Pages 9394-9401Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo501689h
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Funding
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- NSERC
- Alberta Innovates-Technology Futures (AI-TF)
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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.
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