Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling |
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| Authors: | Vanessa Cerezo Jean Martinez Marta Planas |
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| Institution: | a Laboratori d'Innovació en Processos i Productes de Síntesi Orgànica (LIPPSO), Departament de Química, Universitat de Girona, Campus de Montilivi, 17071 Girona, Spain
b Institut des Biomolécules Max Mousseron (IBMM), UMR 5247 CNRS, Université Montpellier 1, Université Montpellier 2, Faculté de Pharmacie, 15 Av. C. Flahault, BP 14 491, 34093 Montpellier Cedex 5, France |
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| Abstract: | Microwave irradiation efficiently promoted the solid-phase Suzuki-Miyaura reaction of a 5-bromohistidine with various arylboronic acids in the presence of a palladium catalyst. This methodology allowed the synthesis of peptides bearing a histidine residue substituted at position 5 of the imidazole ring with a phenyl, a substituted phenyl, a pyridyl, or a thienyl ring, as well as with the benzene ring of a tyrosine residue. |
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| Keywords: | Histidine Arylation Suzuki-Miyaura cross-coupling Microwave Biaryl peptides Solid-phase synthesis |
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