Late‐stage C−H Functionalization of Tryptophan‐Containing Peptides with Thianthrenium Salts: Conjugation and Ligation

Autor: Nikolaos Kaplaneris, Alejandro Puet, Felix Kallert, Julia Pöhlmann, Lutz Ackermann
Rok vydání: 2023
Předmět:
Zdroj: Angewandte Chemie International Edition. 62
ISSN: 1521-3773
1433-7851
DOI: 10.1002/anie.202216661
Popis: Bioorthogonal late-stage diversification of structurally complex peptides bears enormous potential for drug discovery and molecular imaging, among others. Herein, we report on a palladium-catalyzed C─H arylation of tryptophan-containing peptides with easily accessible and modular arylthianthrenium salts. Under exceedingly mild reaction conditions the late-stage diversification of structurally complex peptides was accomplished. The tunability and ease of preparation of arylthianthrenium salts allowed the expedient stitching of tryptophan-containing peptides with drug, natural product, and peptidic scaffolds by forging sterically congested biaryl linkages. The robustness of the palladium catalysis regime was reflected by the full tolerance of a plethora of sensitive and coordinating functional groups. Hence, our manifold enabled efficient access to highly decorated, labelled, conjugated, and ligated linear and cyclic peptides.
Databáze: OpenAIRE
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