Angewandte Chemie International Edition · 2018 · 223 citations · 74 references
Natural SciencesBiochemistryChemistryBiocatalysisCatalysisProtein EngineeringAmino Acid ChemistryCatalytic MechanismsPeptide ChemistryPhotocatalysisPhotochemical SynthesisAmino AcidsAmino FunctionalizationGlycopeptide SynthesisMild Reaction ConditionsPeptide Natural ProductsPost-translationally Modified Peptides
Abstract Despite a well‐developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible‐light‐induced Cu‐catalyzed decarboxylative C(sp 3 )−H alkylation of glycine for preparing α‐alkylated unnatural α‐amino acids. It merits mentioning that the mild conditions and the good functional‐group tolerance allow the modification of peptides using this method. The mechanistic studies revealed that a radical–radical coupling pathway is involved in the reaction.
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