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 - Álvarez, Beatriz - Estrin, Darío A

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.


Detalles Bibliográficos
2022
Cysteine
Persulfide
Alpha effect
Hydrogen sulfide
Sulfhydryl
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