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Late‐Stage Peptide Diversification through Cobalt‐Catalyzed C−H Activation: Sequential Multicatalysis for Stapled Peptides
Author(s) -
Lorion Mélanie M.,
Kaplaneris Nikolaos,
Son Jongwoo,
Kuniyil Rositha,
Ackermann Lutz
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201811668
Subject(s) - bioorthogonal chemistry , peptide , alkene , catalysis , combinatorial chemistry , chemistry , palladium , cobalt , metathesis , stereochemistry , biochemistry , organic chemistry , click chemistry , polymer , polymerization
Abstract Bioorthogonal late‐stage diversification of structurally complex peptides has enormous potential for drug discovery and molecular imaging. In recent years, transition‐metal‐catalyzed C−H activation has emerged as an increasingly viable tool for peptide modification. Despite major accomplishments, these strategies largely rely on expensive palladium catalysts. We herein report an unprecedented cobalt(III)‐catalyzed peptide C−H activation, which enables the direct C−H functionalization of structurally complex peptides, and sets the stage for a multicatalytic C−H activation/alkene metathesis/hydrogenation strategy for the assembly of novel cyclic peptides.