Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes

The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its sit...

Descripción completa

Detalles Bibliográficos
Autores: San Segundo Eizaguirre, Marcos, Correa Navarro, Arkaitz
Tipo de recurso: artículo
Fecha de publicación:2019
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/37535
Acceso en línea:http://hdl.handle.net/10810/37535
Access Level:acceso abierto
Palabra clave:c-h functionalization
amino-acid derivatives
unactivated c(sp(3))-h
palladium
bonds
diversification
activation
arylation
olefination
chemistry
id ES_4c19b65e1658ce0e154ec18519d97418
oai_identifier_str oai:addi.ehu.eus:10810/37535
network_acronym_str ES
network_name_str España
repository_id_str
spelling Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydesSan Segundo Eizaguirre, MarcosCorrea Navarro, Arkaitzc-h functionalizationamino-acid derivativesunactivated c(sp(3))-hpalladiumbondsdiversificationactivationarylationolefinationchemistryThe site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its site-specificity, tolerance of sensitive functional groups, scalability, and enantiospecificity and exhibits entire chemoselectivity for Phe motifs over other amino acid units. The compatibility of this dehydrogenative acylation platform with a number of oligopeptides of high structural complexity illustrates its ample opportunities for the late-stage peptide modification and bioconjugation.We are grateful to MINECO (CTQ2016-78395-P; RTI2018093721-B-I00) and Basque Government (IT1033-16) for. nancial support. A.C. thanks MINECO for a Ramon y Cajal research contract (RYC-2012-09873). We acknowledge technical and human support provided by SGIker of UPV/EHU and European funding (ERDF and ESF). Cost-CHAOS action (CA15106) is also acknowledged.Royal Society of Chemistry202020202019info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/37535reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/MINECO/RYC-2012-09873/info:eu-repo/grantAgreement/MINECO/CTQ2016-78395-P/info:eu-repo/grantAgreement/MINECO/RTI2018093721-B-I00/https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc03425kinfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/es/This journal is © The Royal Society of Chemistry 2019. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.oai:addi.ehu.eus:10810/375352026-06-18T09:23:17Z
dc.title.none.fl_str_mv Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
title Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
spellingShingle Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
San Segundo Eizaguirre, Marcos
c-h functionalization
amino-acid derivatives
unactivated c(sp(3))-h
palladium
bonds
diversification
activation
arylation
olefination
chemistry
title_short Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
title_full Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
title_fullStr Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
title_full_unstemmed Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
title_sort Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides 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 c-h functionalization
amino-acid derivatives
unactivated c(sp(3))-h
palladium
bonds
diversification
activation
arylation
olefination
chemistry
topic c-h functionalization
amino-acid derivatives
unactivated c(sp(3))-h
palladium
bonds
diversification
activation
arylation
olefination
chemistry
description The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its site-specificity, tolerance of sensitive functional groups, scalability, and enantiospecificity and exhibits entire chemoselectivity for Phe motifs over other amino acid units. The compatibility of this dehydrogenative acylation platform with a number of oligopeptides of high structural complexity illustrates its ample opportunities for the late-stage peptide modification and bioconjugation.
publishDate 2019
dc.date.none.fl_str_mv 2019
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/37535
url http://hdl.handle.net/10810/37535
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/MINECO/RYC-2012-09873/
info:eu-repo/grantAgreement/MINECO/CTQ2016-78395-P/
info:eu-repo/grantAgreement/MINECO/RTI2018093721-B-I00/
https://pubs.rsc.org/en/content/articlepdf/2019/sc/c9sc03425k
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/es/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/es/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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
_version_ 1869407605437235200
score 15,301603

Similares en LA Referencia