Late-Stage Pd(II)-Catalyzed C(sp3)-H Functionalization of Peptides Directed by a Removable, Backbone-Inserted Amidoxime Ether

Palladium(II)-catalyzed C-H functionalization has attracted considerable attention as a pathway to late-stage modification of peptides. Herein, we report the Pd-catalyzed C(sp3)-H arylation of peptides directed by an amidoxime ether, which can be easily incorporated into peptides at any amide bond....

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2025-01, p.e202423979
Main Authors: Wu, Yuezhou, Zhu, Beichen, Fan, Haoyang, Bernard, Hugo, Hutton, Craig Anthony
Format: Article
Language:English
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Summary:Palladium(II)-catalyzed C-H functionalization has attracted considerable attention as a pathway to late-stage modification of peptides. Herein, we report the Pd-catalyzed C(sp3)-H arylation of peptides directed by an amidoxime ether, which can be easily incorporated into peptides at any amide bond. Site- and stereoselective arylation of peptides has been achieved, including an unprecedented example of C-H arylation of an internal residue. Removal of the amidoxime ether was achieved to generate the parent amide and facilitate a traceless C-H functionalization process.
ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202423979