Formation and characterization of crosslinks, including Tyr-Trp species, on one electron oxidation of free Tyr and Trp residues by carbonate radical anion

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dc.catalogadorjwg
dc.contributor.authorFigueroa Alegría, Juan David
dc.contributor.authorZarate Méndez, Ana María
dc.contributor.authorFuentes Lemus, Eduardo Felipe
dc.contributor.authorDavies, M. J.
dc.contributor.authorLopez Alarcon Camilo Ignacio
dc.date.accessioned2025-01-02T18:00:01Z
dc.date.available2025-01-02T18:00:01Z
dc.date.issued2020
dc.description.abstractDityrosine and ditryptophan bonds have been implied in protein crosslinking. This is associated with oxidative stress conditions including those involved in neurodegenerative pathologies and age-related processes. Formation of dityrosine and ditryptophan derives from radical-radical reactions involving Tyr(center dot) and Trp(center dot) radicals. However, cross reactions of Tyr(center dot) and Trp(center dot) leading to Tyr-Trp crosslinks and their biological consequences have been less explored. In the present work we hypothesized that exposure of free Tyr and Trp to a high concentration of carbonate anion radicals (CO3 center dot-), under anaerobic conditions, would result in the formation of Tyr-Trp species, as well as dityrosine and ditryptophan crosslinks. Here we report a simple experimental procedure, employing CO3 center dot- generated photochemically by illumination of a Co(iii) complex at 254 nm, that produces micromolar concentrations of Tyr-Trp crosslinks. Analysis by mass spectrometry of solutions containing only the individual amino acids, and the Co(iii) complex, provided evidence for the formation ofo,o '-dityrosine and isodityrosine from Tyr, and three ditryptophan dimers from Trp. When mixtures of Tyr and Trp were illuminated in an identical manner, Tyr-Trp crosslinks were detected together with dityrosine and ditryptophan dimers. These results indicate that there is a balance between the formation of these three classes of crosslinks, which is dependent on the Tyr and Trp concentrations. The methods reported here allow the generation of significant yields of isolated Tyr-Trp adducts and their characterization. This technology should facilitate the detection, and examination of the biological consequences of Tyr-Trp crosslink formation in complex systems in future investigations.
dc.fuente.origenORCID
dc.identifier.converisid1
dc.identifier.doi10.1039/D0RA04051G
dc.identifier.issn2046-2069
dc.identifier.scopusidSCOPUS_ID:2-s2.0-85088458459
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/89459
dc.identifier.wosidWOS:000552843400043
dc.information.autorucEscuela de Química; Figueroa Alegria Juan David; S/I; 1071087
dc.information.autorucEscuela de Química; Zarate Mendez Ana Maria; S/I; 169850
dc.information.autorucEscuela de Química; Fuentes Lemus Eduardo Felipe; 0000-0002-1465-8466; 186720
dc.information.autorucEscuela de Química; Lopez Alarcon Camilo Ignacio; S/I; 1004308
dc.issue.numero43
dc.language.isoen
dc.nota.accesocontenido completo
dc.pagina.final25800
dc.pagina.inicio25786
dc.revistaRSC Advances
dc.rightsacceso restringido
dc.subject.ddc570
dc.subject.deweyBiologíaes_ES
dc.titleFormation and characterization of crosslinks, including Tyr-Trp species, on one electron oxidation of free Tyr and Trp residues by carbonate radical anion
dc.typeartículo
dc.volumen10
sipa.codpersvinculados1071087
sipa.codpersvinculados169850
sipa.codpersvinculados186720
sipa.codpersvinculados1004308
sipa.trazabilidadORCID;2024-12-23
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