Unexpected Formation and Potent Antioxidant Activity of Macrocyclic Dimers Containing Disulfide and Selenide Groups
Date
2022-11-17
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Abstract
During attempts to prepare spirodithiaselenuranes as GPx mimetics, a series of unexpected dimeric macrocycles was obtained, each containing two selenide and two disulfide moieties in rings ranging from 18- to 26-membered. The products showed potent GPx-like activity in an NMR assay based on their ability to catalyze the reduction of hydrogen peroxide with benzyl thiol. The high catalytic activity was attributed to transannular effects during selenide to selenoxide oxidation. This redox process was also characterized by an induction period that indicated autocatalysis in the formation of an intermediate selenoxide from the oxidation of the corresponding selenide.
Description
Keywords
Antioxidants, Autocatalysis, Chalcogen-Containing Macrocycles, GPx Mimetics
Citation
McMillan, J. D. R., Sands, K. N., Cooney, G. S., Gelfand, B. S., & Back, T. G. (n.d.). Unexpected Formation and Potent Antioxidant Activity of Macrocyclic Dimers Containing Disulfide and Selenide Groups. Angewandte Chemie International Edition, n/a(n/a), e202213744. https://doi.org/10.1002/anie.202213744