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Biochalcogen Chemistry The Biological Chemistry Of Sulfur Selenium And Tellurium 2013

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Selenium plays an important role in normal biological function through its incorporation into processes that protect against oxidative stress and promote thyroid function. The complex nature of the mechanisms involved has led to extensive study through computational modeling. However, density functional theory DFT modeling of the redox mechanisms of selenium is complicated by proton exchange processes catalyzed by the bulk solvent.

To address this issue, we have used a method of microsolvation which we have dubbed solvent-assisted proton exchange SAPE.

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These models include a few strategically placed water molecules to act as a proton shuttle and are able to obtain activation barriers that are in good agreement with experimental data and trends. As a first approximation to solution-phase reactivity, SAPE models are more appropriate for drawing conclusions about the trends and energetics of these complex mechanisms.

From these models, we have gained significant insight into the biological pathways of these compounds. In this chapter, we discuss our implementation of SAPE models for redox scavenging by various biorelevant organoselenium compounds, specifically arylselenols, seleninic acids and ebselen, and the related mechanism of cysteine. Finally, we discuss approaches to modeling additional important biochalcogen processes in the thyroid and in zinc finger proteins.

More by Craig A. Chapter 9 pp