Solid-phase synthesis of biaryl cyclic peptides containing a 3-aryltyrosine
A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe-Tyr or a Tyr-Tyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound 3-iodotyrosine and a microwave-assisted Suzuki-Miyaura reaction for the formation of the macrocycle. Fi...
| Autores: | , , , |
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| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2012 |
| País: | España |
| Recursos: | 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:10256/12667 |
| Acesso em linha: | http://hdl.handle.net/10256/12667 |
| Access Level: | acceso embargado |
| Palavra-chave: | Antibiòtics pèptids Peptide antibiotics Pèptids -- Síntesi Peptides -- Synthesis Reacció de Suzuki-Miyaura Suzuki-Miyaura reaction |
| Resumo: | A concise and efficient solid-phase synthesis of biaryl cyclic peptides containing a Phe-Tyr or a Tyr-Tyr linkage has been accomplished. The key steps include a Miyaura borylation of a resin-bound 3-iodotyrosine and a microwave-assisted Suzuki-Miyaura reaction for the formation of the macrocycle. First, the feasibility of the solid-phase Miyaura borylation of a 3-iodotyrosyltripeptide was established. Then, the Suzuki-Miyaura reaction was applied to the cross-coupling of linear 3-boronotyrosine-containing peptidyl resins with iodobenzene and with halogenated aromatic amino acids. Finally, this methodology was extended to the synthesis of biaryl cyclic peptides through the preparation of a linear peptidyl resin containing both the required boronate and halogenated derivatives, followed by a microwave-assisted Suzuki-Miyaura macrocyclization |
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