Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling

A microwave-assisted solid-phase Suzuki-Miyaura reaction has been employed for the synthesis of 5-arylhistidine-containing peptides. In particular, sequences containing a 5-arylhistidine at the 1- or 4-positions have been designed based on lead antimicrobial peptides. The cross-coupling involved the...

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Autores: Ng-Choi, Iteng, Soler Vives, Marta, Cerezo Frias, Vanessa, Badosa Romañó, Esther, Montesinos Seguí, Emilio, Planas i Grabuleda, Marta, Feliu Soley, Lidia
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2012
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10256/12264
Acceso en línea:http://hdl.handle.net/10256/12264
Access Level:acceso embargado
Palabra clave:Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Medicaments antiinfecciosos
Anti-infective agents
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spelling Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-couplingNg-Choi, ItengSoler Vives, MartaCerezo Frias, VanessaBadosa Romañó, EstherMontesinos Seguí, EmilioPlanas i Grabuleda, MartaFeliu Soley, LidiaAntibiòtics pèptidsPeptide antibioticsPèptids -- SíntesiPeptides -- SynthesisMedicaments antiinfecciososAnti-infective agentsA microwave-assisted solid-phase Suzuki-Miyaura reaction has been employed for the synthesis of 5-arylhistidine-containing peptides. In particular, sequences containing a 5-arylhistidine at the 1- or 4-positions have been designed based on lead antimicrobial peptides. The cross-coupling involved the arylation of a resin-bound 5-bromohistidine with an arylboronic acid in solution under microwave irradiation. This protocol is compatible with common protecting groups used in peptide chemistry. The resulting biaryl linear undecapeptides were screened for their antibacterial, antifungal and hemolytic activities. The results showed that the presence of an imidazole ring significantly decreases the cytotoxicity. A solid-phase Suzuki-Miyaura reaction has been applied to the synthesis of 5-arylhistidine undecapeptides. The biaryl peptides displayed low hemolytic antimicrobial activityI. N.-C. thanks the Spanish Ministerio de Ciencia e Innovación (MICINN) for a predoctoral fellowship. This work was supported by MICINN grants, AGL2006-13564/AGR and AGL2009-13255-C02-02/AGRWiley-VCH VerlagMinisterio de Educación y Ciencia (Espanya)Ministerio de Ciencia e Innovación (Espanya)info2012info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10256/12264© European Journal of Organic Chemistry, 2012, núm. 23, p. 4321-4332Articles publicats (D-Q)reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)Inglésinfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201200291info:eu-repo/semantics/altIdentifier/issn/1434-193Xinfo:eu-repo/semantics/altIdentifier/eissn/1099-0690info:eu-repo/grantAgreement/MEC//AGL2006-13564-C02-02info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02Tots els drets reservatsinfo:eu-repo/semantics/embargoedAccessoai:recercat.cat:10256/122642026-05-29T05:05:01Z
dc.title.none.fl_str_mv Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
title Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
spellingShingle Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
Ng-Choi, Iteng
Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Medicaments antiinfecciosos
Anti-infective agents
title_short Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
title_full Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
title_fullStr Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
title_full_unstemmed Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
title_sort Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
dc.creator.none.fl_str_mv Ng-Choi, Iteng
Soler Vives, Marta
Cerezo Frias, Vanessa
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
author Ng-Choi, Iteng
author_facet Ng-Choi, Iteng
Soler Vives, Marta
Cerezo Frias, Vanessa
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
author_role author
author2 Soler Vives, Marta
Cerezo Frias, Vanessa
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lidia
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Educación y Ciencia (Espanya)
Ministerio de Ciencia e Innovación (Espanya)
dc.subject.none.fl_str_mv Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Medicaments antiinfecciosos
Anti-infective agents
topic Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Medicaments antiinfecciosos
Anti-infective agents
description A microwave-assisted solid-phase Suzuki-Miyaura reaction has been employed for the synthesis of 5-arylhistidine-containing peptides. In particular, sequences containing a 5-arylhistidine at the 1- or 4-positions have been designed based on lead antimicrobial peptides. The cross-coupling involved the arylation of a resin-bound 5-bromohistidine with an arylboronic acid in solution under microwave irradiation. This protocol is compatible with common protecting groups used in peptide chemistry. The resulting biaryl linear undecapeptides were screened for their antibacterial, antifungal and hemolytic activities. The results showed that the presence of an imidazole ring significantly decreases the cytotoxicity. A solid-phase Suzuki-Miyaura reaction has been applied to the synthesis of 5-arylhistidine undecapeptides. The biaryl peptides displayed low hemolytic antimicrobial activity
publishDate 2012
dc.date.none.fl_str_mv 2012
info
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10256/12264
url http://hdl.handle.net/10256/12264
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201200291
info:eu-repo/semantics/altIdentifier/issn/1434-193X
info:eu-repo/semantics/altIdentifier/eissn/1099-0690
info:eu-repo/grantAgreement/MEC//AGL2006-13564-C02-02
info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02
dc.rights.none.fl_str_mv Tots els drets reservats
info:eu-repo/semantics/embargoedAccess
rights_invalid_str_mv Tots els drets reservats
eu_rights_str_mv embargoedAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH Verlag
publisher.none.fl_str_mv Wiley-VCH Verlag
dc.source.none.fl_str_mv © European Journal of Organic Chemistry, 2012, núm. 23, p. 4321-4332
Articles publicats (D-Q)
reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.812429

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