Possible molecular basis of the biochemical effects of cysteine-derived persulfides
Resumen:
Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/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.
2022 | |
Cysteine Persulfide Alpha effect Hydrogen sulfide Sulfhydryl |
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Inglés | |
Universidad de la República | |
COLIBRI | |
https://hdl.handle.net/20.500.12008/41547 | |
Acceso abierto | |
Licencia Creative Commons Atribución (CC - By 4.0) |
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author | Cuevasanta, Ernesto |
author2 | Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Álvarez, Beatriz Estrin, Darío A |
author2_role | author author author author author author author |
author_facet | Cuevasanta, Ernesto Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Álvarez, Beatriz Estrin, Darío A |
author_role | author |
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collection | COLIBRI |
dc.contributor.filiacion.none.fl_str_mv | Cuevasanta Ernesto, Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica. Benchoam Dayana, Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica. Semelak Jonathan A. Möller Matías N., Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica. Zeida Ari, Universidad de la República (Uruguay). Facultad de Medicina. Trujillo Madia, Universidad de la República (Uruguay). Facultad de Medicina. Álvarez Beatriz, Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica. Estrin Darío A |
dc.creator.none.fl_str_mv | Cuevasanta, Ernesto Benchoam, Dayana Semelak, Jonathan A. Möller, Matías N. Zeida, Ari Trujillo, Madia Álvarez, Beatriz Estrin, Darío A |
dc.date.accessioned.none.fl_str_mv | 2023-11-29T13:04:26Z |
dc.date.available.none.fl_str_mv | 2023-11-29T13:04:26Z |
dc.date.issued.none.fl_str_mv | 2022 |
dc.description.abstract.none.fl_txt_mv | Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/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. |
dc.format.extent.es.fl_str_mv | 9 h. |
dc.format.mimetype.es.fl_str_mv | application/pdf |
dc.identifier.citation.es.fl_str_mv | Cuevasanta, E, Benchoam, D, Semelak, J, [y otros autores]. "Possible molecular basis of the biochemical effects of cysteine-derived persulfides". Frontiers in Molecular Biosciences. [en línea] 2022, 9: 975988. 9 h. DOI: 10.3389/fmolb.2022.975988 |
dc.identifier.doi.none.fl_str_mv | 10.3389/fmolb.2022.975988 |
dc.identifier.issn.none.fl_str_mv | 2296-889X |
dc.identifier.uri.none.fl_str_mv | https://hdl.handle.net/20.500.12008/41547 |
dc.language.iso.none.fl_str_mv | en eng |
dc.publisher.es.fl_str_mv | Frontiers Media |
dc.relation.ispartof.es.fl_str_mv | Frontiers in Molecular Biosciences, 2022, 9: 975988 |
dc.rights.license.none.fl_str_mv | Licencia Creative Commons Atribución (CC - By 4.0) |
dc.rights.none.fl_str_mv | info:eu-repo/semantics/openAccess |
dc.source.none.fl_str_mv | reponame:COLIBRI instname:Universidad de la República instacron:Universidad de la República |
dc.subject.es.fl_str_mv | Cysteine Persulfide Alpha effect Hydrogen sulfide Sulfhydryl |
dc.title.none.fl_str_mv | Possible molecular basis of the biochemical effects of cysteine-derived persulfides |
dc.type.es.fl_str_mv | Artículo |
dc.type.none.fl_str_mv | info:eu-repo/semantics/article |
dc.type.version.none.fl_str_mv | info:eu-repo/semantics/publishedVersion |
description | Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/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. |
eu_rights_str_mv | openAccess |
format | article |
id | COLIBRI_5274c94c7a43ada68818ada492dafb88 |
identifier_str_mv | Cuevasanta, E, Benchoam, D, Semelak, J, [y otros autores]. "Possible molecular basis of the biochemical effects of cysteine-derived persulfides". Frontiers in Molecular Biosciences. [en línea] 2022, 9: 975988. 9 h. DOI: 10.3389/fmolb.2022.975988 2296-889X 10.3389/fmolb.2022.975988 |
instacron_str | Universidad de la República |
institution | Universidad de la República |
instname_str | Universidad de la República |
language | eng |
language_invalid_str_mv | en |
network_acronym_str | COLIBRI |
network_name_str | COLIBRI |
oai_identifier_str | oai:colibri.udelar.edu.uy:20.500.12008/41547 |
publishDate | 2022 |
reponame_str | COLIBRI |
repository.mail.fl_str_mv | mabel.seroubian@seciu.edu.uy |
repository.name.fl_str_mv | COLIBRI - Universidad de la República |
repository_id_str | 4771 |
rights_invalid_str_mv | Licencia Creative Commons Atribución (CC - By 4.0) |
spelling | Cuevasanta Ernesto, Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica.Benchoam Dayana, Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica.Semelak Jonathan A.Möller Matías N., Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica.Zeida Ari, Universidad de la República (Uruguay). Facultad de Medicina.Trujillo Madia, Universidad de la República (Uruguay). Facultad de Medicina.Álvarez Beatriz, Universidad de la República (Uruguay). Facultad de Ciencias. Instituto de Química Biológica.Estrin Darío A2023-11-29T13:04:26Z2023-11-29T13:04:26Z2022Cuevasanta, E, Benchoam, D, Semelak, J, [y otros autores]. "Possible molecular basis of the biochemical effects of cysteine-derived persulfides". Frontiers in Molecular Biosciences. [en línea] 2022, 9: 975988. 9 h. DOI: 10.3389/fmolb.2022.9759882296-889Xhttps://hdl.handle.net/20.500.12008/4154710.3389/fmolb.2022.975988Persulfides (RSSH/RSS−) are species closely related to thiols (RSH/RS−) and hydrogen sulfide (H2S/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.Submitted by Festari Camila (camifestari@gmail.com) on 2023-11-26T06:06:08Z No. of bitstreams: 2 license_rdf: 24251 bytes, checksum: 71ed42ef0a0b648670f707320be37b90 (MD5) 10.3389fmolb.2022.975988.pdf: 1501427 bytes, checksum: f11e8e10a1dacc233ab111f3903f8602 (MD5)Approved for entry into archive by Faget Cecilia (lfaget@fcien.edu.uy) on 2023-11-29T12:58:02Z (GMT) No. of bitstreams: 2 license_rdf: 24251 bytes, checksum: 71ed42ef0a0b648670f707320be37b90 (MD5) 10.3389fmolb.2022.975988.pdf: 1501427 bytes, checksum: f11e8e10a1dacc233ab111f3903f8602 (MD5)Made available in DSpace by Luna Fabiana (fabiana.luna@seciu.edu.uy) on 2023-11-29T13:04:26Z (GMT). No. of bitstreams: 2 license_rdf: 24251 bytes, checksum: 71ed42ef0a0b648670f707320be37b90 (MD5) 10.3389fmolb.2022.975988.pdf: 1501427 bytes, checksum: f11e8e10a1dacc233ab111f3903f8602 (MD5) Previous issue date: 20229 h.application/pdfenengFrontiers MediaFrontiers in Molecular Biosciences, 2022, 9: 975988Las obras depositadas en el Repositorio se rigen por la Ordenanza de los Derechos de la Propiedad Intelectual de la Universidad de la República.(Res. Nº 91 de C.D.C. de 8/III/1994 – D.O. 7/IV/1994) y por la Ordenanza del Repositorio Abierto de la Universidad de la República (Res. 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- Universidad de la Repúblicafalse |
spellingShingle | Possible molecular basis of the biochemical effects of cysteine-derived persulfides Cuevasanta, Ernesto Cysteine Persulfide Alpha effect Hydrogen sulfide Sulfhydryl |
status_str | publishedVersion |
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 | Cysteine Persulfide Alpha effect Hydrogen sulfide Sulfhydryl |
url | https://hdl.handle.net/20.500.12008/41547 |