Pd-catalyzed site-selective C(sp(2)-H radical acylation of phenylalanine containing peptides with aldehydes
The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its sit...
| Autores: | , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2019 |
| País: | España |
| Institución: | Universidad del País Vasco |
| Repositorio: | Addi. Archivo Digital para la Docencia y la Investigación |
| OAI Identifier: | oai:addi.ehu.eus:10810/37535 |
| Acceso en línea: | http://hdl.handle.net/10810/37535 |
| Access Level: | acceso abierto |
| Palabra clave: | c-h functionalization amino-acid derivatives unactivated c(sp(3))-h palladium bonds diversification activation arylation olefination chemistry |
| Sumario: | The site-selective functionalization of C-H bonds within a peptide framework remains a challenging task of prime synthetic importance. Herein, the first Pd-catalyzed delta-C(sp(2))-H acylation of Phe containing peptides with aldehydes is described. This oxidative coupling is distinguished by its site-specificity, tolerance of sensitive functional groups, scalability, and enantiospecificity and exhibits entire chemoselectivity for Phe motifs over other amino acid units. The compatibility of this dehydrogenative acylation platform with a number of oligopeptides of high structural complexity illustrates its ample opportunities for the late-stage peptide modification and bioconjugation. |
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