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...
| Autores: | , , , , , , |
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| 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 |
| Sumario: | 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 |
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