Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes

The development of useful synthetic tools to label amino acids within a peptide framework for the ultimate modification of proteins in a late-stage fashion is a challenging task of utmost importance within chemical biology. Herein, we report the first Pd-catalyzed C–H acylation of a collection of Ty...

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Detalles Bibliográficos
Autores: San Segundo Eizaguirre, Marcos, Correa Navarro, Arkaitz
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/50910
Acceso en línea:http://hdl.handle.net/10810/50910
Access Level:acceso abierto
Palabra clave:site-selectivity
acylation
radical chemistry
late-stage peptide modification
bioconjugation
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spelling Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with AldehydesSan Segundo Eizaguirre, MarcosCorrea Navarro, Arkaitzsite-selectivityacylationradical chemistrylate-stage peptide modificationbioconjugationThe development of useful synthetic tools to label amino acids within a peptide framework for the ultimate modification of proteins in a late-stage fashion is a challenging task of utmost importance within chemical biology. Herein, we report the first Pd-catalyzed C–H acylation of a collection of Tyr-containing peptides with aldehydes. This water-compatible tagging technique is distinguished by its site-specificity, scalability and full tolerance of sensitive functional groups. Remarkably, it provides straightforward access to a high number of oligopeptides with altered side-chain topology including mimetics of endomorphin-2 and neuromedin N, thus illustrating its promising perspectives toward the diversification of structurally complex peptides and chemical ligationWe are grateful to Ministerio de Ciencia e Innovación (RTI2018-093721-B-I00, MCI/AEI/FEDER, UE) and Basque Government (IT1033-16) for financial support. We thank for technical and human support provided by Central Service of Analysis-SGIker of UPV/EHU and European funding (ERDF and ESF).RSC202120212020info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/50910reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MCIN/RTI2018-093721-B-I00/https://pubs.rsc.org/en/content/articlelanding/2020/SC/D0SC03791Einfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc/3.0/(cc) 2020 Royal Society of Chemistry (cc by-nc 3.0)oai:addi.ehu.eus:10810/509102026-06-18T09:23:17Z
dc.title.none.fl_str_mv Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
title Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
spellingShingle Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
San Segundo Eizaguirre, Marcos
site-selectivity
acylation
radical chemistry
late-stage peptide modification
bioconjugation
title_short Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
title_full Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
title_fullStr Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
title_full_unstemmed Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
title_sort Site-Selective Aqueous C–H Acylation of Tyrosine-Containing Oligopeptides with Aldehydes
dc.creator.none.fl_str_mv San Segundo Eizaguirre, Marcos
Correa Navarro, Arkaitz
author San Segundo Eizaguirre, Marcos
author_facet San Segundo Eizaguirre, Marcos
Correa Navarro, Arkaitz
author_role author
author2 Correa Navarro, Arkaitz
author2_role author
dc.subject.none.fl_str_mv site-selectivity
acylation
radical chemistry
late-stage peptide modification
bioconjugation
topic site-selectivity
acylation
radical chemistry
late-stage peptide modification
bioconjugation
description The development of useful synthetic tools to label amino acids within a peptide framework for the ultimate modification of proteins in a late-stage fashion is a challenging task of utmost importance within chemical biology. Herein, we report the first Pd-catalyzed C–H acylation of a collection of Tyr-containing peptides with aldehydes. This water-compatible tagging technique is distinguished by its site-specificity, scalability and full tolerance of sensitive functional groups. Remarkably, it provides straightforward access to a high number of oligopeptides with altered side-chain topology including mimetics of endomorphin-2 and neuromedin N, thus illustrating its promising perspectives toward the diversification of structurally complex peptides and chemical ligation
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/50910
url http://hdl.handle.net/10810/50910
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MCIN/RTI2018-093721-B-I00/
https://pubs.rsc.org/en/content/articlelanding/2020/SC/D0SC03791E
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc/3.0/
(cc) 2020 Royal Society of Chemistry (cc by-nc 3.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc/3.0/
(cc) 2020 Royal Society of Chemistry (cc by-nc 3.0)
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv RSC
publisher.none.fl_str_mv RSC
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
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