Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation

The development of efficient metal-promoted bioorthogonal ligations remains as a major scientific challenge. Demonstrated herein is that azides undergo efficient and regioselective room-temperature annulations with thioalkynes in aqueous milieu when treated with catalytic amounts of a suitable ruthe...

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Autores: Destito, Paolo, Rodríguez Couceiro, José, Faustino, Hélio, López García, Fernando, Mascareñas Cid, José Luis
Tipo de recurso: artículo
Fecha de publicación:2017
País:España
Institución:Universidad de Santiago de Compostela (USC)
Repositorio:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
Idioma:inglés
OAI Identifier:oai:minerva.usc.gal:10347/15804
Acceso en línea:http://hdl.handle.net/10347/15804
Access Level:acceso abierto
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spelling Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical LigationDestito, PaoloRodríguez Couceiro, JoséFaustino, HélioLópez García, FernandoMascareñas Cid, José LuisThe development of efficient metal-promoted bioorthogonal ligations remains as a major scientific challenge. Demonstrated herein is that azides undergo efficient and regioselective room-temperature annulations with thioalkynes in aqueous milieu when treated with catalytic amounts of a suitable ruthenium complex. The reaction is compatible with different biomolecules, and can be carried out in complex aqueous mixtures such as phosphate buffered saline, cell lysates, fetal bovine serum, and even living bacteria (E. coli). Importantly, the reaction is mutually compatible with the classical CuAACWileyUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais MolecularesUniversidade de Santiago de Compostela. Departamento de Química Orgánica20172017-08-0320172017-08-03journal articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10347/15804reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostelainstname:Universidad de Santiago de Compostela (USC)InglésengEuropean Commission http://dx.doi.org/10.13039/501100000780 Seventh Framework Programme 340055Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2016-76689-RMinisterio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2013-41943-R HERRAMIENTAS SINTETICAS EN QUIMICA BIOLOGICA. NUEVAS ESTRATEGIAS MOLECULARES PARA EL TRATAMIENTO Y DIAGNOSTICO DE CANCERESopen accesshttp://purl.org/coar/access_right/c_abf2© 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are madehttps://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:minerva.usc.gal:10347/158042026-06-15T12:47:27Z
dc.title.none.fl_str_mv Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
title Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
spellingShingle Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
Destito, Paolo
title_short Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
title_full Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
title_fullStr Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
title_full_unstemmed Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
title_sort Ruthenium-Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
dc.creator.none.fl_str_mv Destito, Paolo
Rodríguez Couceiro, José
Faustino, Hélio
López García, Fernando
Mascareñas Cid, José Luis
author Destito, Paolo
author_facet Destito, Paolo
Rodríguez Couceiro, José
Faustino, Hélio
López García, Fernando
Mascareñas Cid, José Luis
author_role author
author2 Rodríguez Couceiro, José
Faustino, Hélio
López García, Fernando
Mascareñas Cid, José Luis
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares
Universidade de Santiago de Compostela. Departamento de Química Orgánica
description The development of efficient metal-promoted bioorthogonal ligations remains as a major scientific challenge. Demonstrated herein is that azides undergo efficient and regioselective room-temperature annulations with thioalkynes in aqueous milieu when treated with catalytic amounts of a suitable ruthenium complex. The reaction is compatible with different biomolecules, and can be carried out in complex aqueous mixtures such as phosphate buffered saline, cell lysates, fetal bovine serum, and even living bacteria (E. coli). Importantly, the reaction is mutually compatible with the classical CuAAC
publishDate 2017
dc.date.none.fl_str_mv 2017
2017-08-03
2017
2017-08-03
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10347/15804
url http://hdl.handle.net/10347/15804
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv European Commission http://dx.doi.org/10.13039/501100000780 Seventh Framework Programme 340055
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2016-76689-R
Ministerio de Economía y Competitividad http://dx.doi.org/10.13039/501100003329 Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016 SAF2013-41943-R HERRAMIENTAS SINTETICAS EN QUIMICA BIOLOGICA. NUEVAS ESTRATEGIAS MOLECULARES PARA EL TRATAMIENTO Y DIAGNOSTICO DE CANCERES
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
instname:Universidad de Santiago de Compostela (USC)
instname_str Universidad de Santiago de Compostela (USC)
reponame_str Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
collection Minerva. Repositorio Institucional de la Universidad de Santiago de Compostela
repository.name.fl_str_mv
repository.mail.fl_str_mv
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