Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols

The selective tagging of amino acids within a peptide framework while using atom-economical C-H counterparts poses an unmet challenge within peptide chemistry. Herein, we report a novel Pd-catalyzed late-stage C-H acylation of a collection of Tyr-containing peptides with alcohols. This water-compati...

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Autores: Urruzuno Guiu, Iñaki, Andrade Sampedro, Paula, Correa Navarro, Arkaitz
Tipo de documento: artigo
Data de publicação:2021
País:España
Recursos:Universidad del País Vasco
Repositório:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/53370
Acesso em linha:http://hdl.handle.net/10810/53370
Access Level:Acceso aberto
Palavra-chave:catalyzed ortho-alkoxylation
bond
functionalization
derivatives
activation
peptides
toolbox
phenols
ethanol
acids
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spelling Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with AlcoholsUrruzuno Guiu, IñakiAndrade Sampedro, PaulaCorrea Navarro, Arkaitzcatalyzed ortho-alkoxylationbondfunctionalizationderivativesactivationpeptidestoolboxphenolsethanolacidsThe selective tagging of amino acids within a peptide framework while using atom-economical C-H counterparts poses an unmet challenge within peptide chemistry. Herein, we report a novel Pd-catalyzed late-stage C-H acylation of a collection of Tyr-containing peptides with alcohols. This water-compatible labeling technique is distinguished by its reliable scalability and features the use of ethanol as a renewable feedstock for the assembly of a variety of peptidomimetics.The authors are grateful to the Ministerio de Ciencia e Innovacion (RTI2018-093721-B-I00, MCI/AEI/FEDER, UE) and the Basque Government (IT1033-16) for financial support. The authors thank the technical and human support provided by the Central Service of Analysis-SGIker of UPV/EHU and European funding (ERDF and ESF). In~aki Urruzuno thanks UPV/EHU for the postdoctoral research grant (EspDoc2020)American Chemical Society202120212021info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/53370reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MICINN/RTI2018-093721-B-I00/https://pubs-acs-org.ehu.idm.oclc.org/doi/10.1021/acs.orglett.1c02764info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/es/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY 4.0)Atribución 3.0 Españaoai:addi.ehu.eus:10810/533702026-06-18T09:23:17Z
dc.title.none.fl_str_mv Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
title Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
spellingShingle Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
Urruzuno Guiu, Iñaki
catalyzed ortho-alkoxylation
bond
functionalization
derivatives
activation
peptides
toolbox
phenols
ethanol
acids
title_short Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
title_full Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
title_fullStr Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
title_full_unstemmed Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
title_sort Late-Stage C-H Acylation of Tyrosine-Containing Oligopeptides with Alcohols
dc.creator.none.fl_str_mv Urruzuno Guiu, Iñaki
Andrade Sampedro, Paula
Correa Navarro, Arkaitz
author Urruzuno Guiu, Iñaki
author_facet Urruzuno Guiu, Iñaki
Andrade Sampedro, Paula
Correa Navarro, Arkaitz
author_role author
author2 Andrade Sampedro, Paula
Correa Navarro, Arkaitz
author2_role author
author
dc.subject.none.fl_str_mv catalyzed ortho-alkoxylation
bond
functionalization
derivatives
activation
peptides
toolbox
phenols
ethanol
acids
topic catalyzed ortho-alkoxylation
bond
functionalization
derivatives
activation
peptides
toolbox
phenols
ethanol
acids
description The selective tagging of amino acids within a peptide framework while using atom-economical C-H counterparts poses an unmet challenge within peptide chemistry. Herein, we report a novel Pd-catalyzed late-stage C-H acylation of a collection of Tyr-containing peptides with alcohols. This water-compatible labeling technique is distinguished by its reliable scalability and features the use of ethanol as a renewable feedstock for the assembly of a variety of peptidomimetics.
publishDate 2021
dc.date.none.fl_str_mv 2021
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/10810/53370
url http://hdl.handle.net/10810/53370
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MICINN/RTI2018-093721-B-I00/
https://pubs-acs-org.ehu.idm.oclc.org/doi/10.1021/acs.orglett.1c02764
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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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score 15,301603

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