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Biological Chemistry

Editor-in-Chief: Brüne, Bernhard

Editorial Board Member: Buchner, Johannes / Ludwig, Stephan / Sies, Helmut / Turk, Boris / Wittinghofer, Alfred

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Selenium in chemistry and biochemistry in comparison to sulfur

Ludger A. Wessjohann1 / Alex Schneider2 / Muhammad Abbas3 / Wolfgang Brandt4

1Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale, Germany

2Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale, Germany

3Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale, Germany

4Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale, Germany

Corresponding author

Citation Information: Biological Chemistry. Volume 388, Issue 10, Pages 997–1006, ISSN (Online) 14374315, ISSN (Print) 14316730, DOI: 10.1515/BC.2007.138, October 2007

Publication History

Published Online:
2007-10-16

Abstract

What makes selenoenzymes – seen from a chemist's view – so special that they cannot be substituted by just more analogous or adapted sulfur proteins? This review compiles and compares physicochemical properties of selenium and sulfur, synthetic routes to selenocysteine (Sec) and its peptides, and comparative studies of relevant thiols and selenols and their (mixed) dichalcogens, required to understand the special role of selenium in selenoproteins on the atomic molecular level. The biochemically most relevant differences are the higher polarizability of Se- and the lower pK a of SeH. The latter has a strikingly different pH-dependence than thiols, with selenols being active at much lower pH. Finally, selected typical enzymatic mechanisms which involve selenocysteine are critically discussed, also in view of the authors' own results.

Keywords: disulfide/diselenide/selenenylsulfide interchange; enzyme mechanisms; selenocysteine; selenoproteins; synthesis

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