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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

© European Journal of Organic Chemistry, 2012, núm. 23, p. 4321-4332

Wiley-VCH Verlag

Author: Ng-Choi, Iteng
Soler Vives, Marta
Cerezo Frias, Vanessa
Badosa Romañó, Esther
Montesinos Seguí, Emilio
Planas i Grabuleda, Marta
Feliu Soley, Lídia
Date: 2012
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
ISSN: 1434-193X (versió paper)
1099-0690 (versió electrònica)
Document access: http://hdl.handle.net/10256/12264
Language: eng
Publisher: Wiley-VCH Verlag
Collection: MEC/PN 2006-2009/ AGL2006-13564-C02-02/AGR
MICINN/PN 2010-2012/ AGL2009-13255-C02-02
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201200291
Articles publicats (D-Q)
Is part of: © European Journal of Organic Chemistry, 2012, núm. 23, p. 4321-4332
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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