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Possible molecular basis of the biochemical effects of cysteine-derived persulfides
Persulfides (RSSH/RSS(−)) are species closely related to thiols (RSH/RS(−)) and hydrogen sulfide (H(2)S/HS(−)), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have be...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9538486/ https://www.ncbi.nlm.nih.gov/pubmed/36213129 http://dx.doi.org/10.3389/fmolb.2022.975988 |
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author | Cuevasanta, Ernesto Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Alvarez, Beatriz Estrin, Darío A. |
author_facet | Cuevasanta, Ernesto Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Alvarez, Beatriz Estrin, Darío A. |
author_sort | Cuevasanta, Ernesto |
collection | PubMed |
description | Persulfides (RSSH/RSS(−)) are species closely related to thiols (RSH/RS(−)) and hydrogen sulfide (H(2)S/HS(−)), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have been proposed to participate in the transduction of hydrogen sulfide effects. Persulfides are acidic, more acidic than thiols, and the persulfide anions are expected to be the predominant species at neutral pH. The persulfide anion has high nucleophilicity, due in part to the alpha effect, i.e., the increased reactivity of a nucleophile when the neighboring atom has high electron density. In addition, persulfides have electrophilic character, a property that is absent in both thiols and hydrogen sulfide. In this article, the biochemistry of persulfides is described, and the possible ways in which the formation of a persulfide could impact on the properties of the biomolecule involved are discussed. |
format | Online Article Text |
id | pubmed-9538486 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-95384862022-10-08 Possible molecular basis of the biochemical effects of cysteine-derived persulfides Cuevasanta, Ernesto Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Alvarez, Beatriz Estrin, Darío A. Front Mol Biosci Molecular Biosciences Persulfides (RSSH/RSS(−)) are species closely related to thiols (RSH/RS(−)) and hydrogen sulfide (H(2)S/HS(−)), and can be formed in biological systems in both low and high molecular weight cysteine-containing compounds. They are key intermediates in catabolic and biosynthetic processes, and have been proposed to participate in the transduction of hydrogen sulfide effects. Persulfides are acidic, more acidic than thiols, and the persulfide anions are expected to be the predominant species at neutral pH. The persulfide anion has high nucleophilicity, due in part to the alpha effect, i.e., the increased reactivity of a nucleophile when the neighboring atom has high electron density. In addition, persulfides have electrophilic character, a property that is absent in both thiols and hydrogen sulfide. In this article, the biochemistry of persulfides is described, and the possible ways in which the formation of a persulfide could impact on the properties of the biomolecule involved are discussed. Frontiers Media S.A. 2022-09-23 /pmc/articles/PMC9538486/ /pubmed/36213129 http://dx.doi.org/10.3389/fmolb.2022.975988 Text en Copyright © 2022 Cuevasanta, Benchoam, Semelak, Möller, Zeida, Trujillo, Alvarez and Estrin. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Molecular Biosciences Cuevasanta, Ernesto Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Alvarez, Beatriz Estrin, Darío A. Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
title | Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
title_full | Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
title_fullStr | Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
title_full_unstemmed | Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
title_short | Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
title_sort | possible molecular basis of the biochemical effects of cysteine-derived persulfides |
topic | Molecular Biosciences |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9538486/ https://www.ncbi.nlm.nih.gov/pubmed/36213129 http://dx.doi.org/10.3389/fmolb.2022.975988 |
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