Why Nature Chose Selenium

Reich, Hans J.; Hondal, Robert J.

doi:10.1021/acschembio.6b00031

Cited by 923Organoselenium and organotellurium chemistrySelenium in Biological SystemsRedox biology and oxidative stress

Why Nature Chose Selenium

Reich, Hans J., Hondal, Robert J.·2016·ACS Chemical Biology

DOI 10.1021/acschembio.6b00031

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Abstract

The authors were asked by the Editors of ACS Chemical Biology to write an article titled "Why Nature Chose Selenium" for the occasion of the upcoming bicentennial of the discovery of selenium by the Swedish chemist Jöns Jacob Berzelius in 1817 and styled after the famous work of Frank Westheimer on the biological chemistry of phosphate [Westheimer, F. H. (1987) Why Nature Chose Phosphates, Science 235, 1173-1178]. This work gives a history of the important discoveries of the biological processes that selenium participates in, and a point-by-point comparison of the chemistry of selenium with the atom it replaces in biology, sulfur. This analysis shows that redox chemistry is the largest chemical difference between the two chalcogens. This difference is very large for both one-electron and two-electron redox reactions. Much of this difference is due to the inability of selenium to form π bonds of all types. The outer valence electrons of selenium are also more loosely held than those of sulfur. As a result, selenium is a better nucleophile and will react with reactive oxygen species faster than sulfur, but the resulting lack of π-bond character in the Se-O bond means that the Se-oxide can be much more readily reduced in comparison to S-oxides. The combination of these properties means that replacement of sulfur with selenium in nature results in a selenium-containing biomolecule that resists permanent oxidation. Multiple examples of this gain of function behavior from the literature are discussed.

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From The Role of Antioxidants in the Interplay between Oxidative Stress and Senescence (2022) · cites this paper as [439]

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Combined Selenium and Vitamin E Deficiency Causes Fatal Myopathy in Guinea Pigs
Hill, K. E., Motley, A. K., Li, X., May, J. M., & Burk, R. F. (2001) · Journal of Nutrition · doi:10.1093/jn/131.6.1798 · Cited by 60 · see citing works
Oxidation of alcohols using benzeneseleninic anhydride
Barton, D. H. R., Brewster, A. G., Hui, R. A. H. F., et al. (1978) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39780000952 · Cited by 58 · see citing works
Evolution of selenoproteins in the metazoan
Jiang, L., Ni, J., & Liu, Q. (2012) · BMC Genomics · doi:10.1186/1471-2164-13-446 · Cited by 57 · see citing works

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Targeting the Thioredoxin System for Cancer Therapy
Zhang, J., Li, X., Han, X., Liu, R., & Fang, J. (2017) · Trends in Pharmacological Sciences · doi:10.1016/j.tips.2017.06.001 · Cited by 460 · see citing works
The Role of Antioxidants in the Interplay between Oxidative Stress and Senescence
Varesi, A., Chirumbolo, S., Campagnoli, L. I. M., Pierella, E., Piccini, G. B., Carrara, A., Ricevuti, G., Scassellati, C., Bonvicini, C., & Pascale, A. (2022) · Antioxidants · doi:10.3390/antiox11071224 · Cited by 145 · see citing works

Authors: Reich, H. J., & Hondal, R. J.
Affiliations: University of Wisconsin–Madison (US)
University of Vermont (US)
Corresponding author: Reich, Hans J.
Hondal, Robert J.
ORCID: Hondal, Robert J.
Venue: ACS Chemical Biology
Publisher: American Chemical Society (ACS)
Published: 2016-03-21
Volume: 11
Issue: 4
Pages: 821-841
ISSN: 1554-8929 (ISSN-L)
1554-8937
DOI: 10.1021/acschembio.6b00031
OpenAlex: W2294386056
Cited by: 923
References: 269
Citations by year: 2026: 84 · 2025: 115 · 2024: 113 · 2023: 111 · 2022: 117 · 2021: 84 · 2020: 79 · 2019: 76 · 2018: 81 · 2017: 49 · 2016: 13
FWCI: 11.13
Type: journal article
Language: en
Open access: closed
Locations: ACS Chemical Biology (publishedVersion)
PubMed (publishedVersion)
Funders: Vanderbilt University
University of Vermont
Università degli Studi dell'Aquila
Topics: Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Toxicology › Organoselenium and organotellurium chemistry
Health Sciences › Nursing › Nutrition and Dietetics › Selenium in Biological Systems
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
Keywords: selenium, sulfur, chalcogens, redox chemistry, π-bonding, nucleophilicity, reactive oxygen species, oxidation resistance
MeSH terms: Deficiency Diseases, Humans, Neoplasms, Selenium, Nature

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