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
dc.description.sponsorship
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
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application/pdf
dc.language.iso
eng
dc.publisher
Wiley-VCH Verlag
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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/
dc.relation.isformatof
Reproducció digital del document publicat a: http://dx.doi.org/10.1002/ejoc.201200291