Cu-Catalyzed Site-Selective C(sp2)–H Radical Trifluoromethylation of Tryptophan Containing Peptides

Site-selective functionalization of C–H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp2)–H trifluoromethylation of tryptophan (Trp)-containing peptides. This fluorination technique is characterized by its chi...

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Detalles Bibliográficos
Autores: Guerrero Azurmendi, Itziar, Correa Navarro, Arkaitz
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/49766
Acceso en línea:http://hdl.handle.net/10810/49766
Access Level:acceso abierto
Palabra clave:trifluoromethylation
peptides
tryptophan
Descripción
Sumario:Site-selective functionalization of C–H bonds within a peptide framework poses a challenging task of paramount synthetic relevance. Herein, we report an operationally simple C(sp2)–H trifluoromethylation of tryptophan (Trp)-containing peptides. This fluorination technique is characterized by its chirality preservation, tolerance of functional groups, and scalability and exhibits chemoselectivity for Trp residues over other amino acid and heterocyclic units. As a result, it represents a sustainable tool toward the late-stage peptide modification and protein engineering.