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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 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

I. 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/AGR

Wiley-VCH Verlag

Manager: Ministerio de Educación y Ciencia (Espanya)
Ministerio de Ciencia e Innovación (Espanya)
Author: Ng-Choi, Iteng
Soler Vives, Marta
Cerezo Frias, Vanessa
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lídia
Abstract: 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
I. 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/AGR
Format: application/pdf
Document access: http://hdl.handle.net/10256/12264
Language: eng
Publisher: Wiley-VCH Verlag
Collection: 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/ES/DESARROLLO DE METODOS DE CONTROL DEL FUEGO BACTERIANO. NUEVOS PEPTIDOS ANTIMICROBIANOS SINTETICOS/
info:eu-repo/grantAgreement/MICINN//AGL2009-13255-C02-02/ES/Control Biotecnologico Del Fuego Bacteriano. Utilizacion De Peptidos Antimicrobianos Sinteticos Derivados De Bacteriocinas Y De Ciclolipopeptidos/
Rights: Tots els drets reservats
Subject: Antibiòtics pèptids
Peptide antibiotics
Pèptids -- Síntesi
Peptides -- Synthesis
Medicaments antiinfecciosos
Anti-infective agents
Title: Solid-phase synthesis of 5-arylhistidine-containing peptides with antimicrobial activity through a microwave-assisted Suzuki-Miyaura cross-coupling
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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