Pd-Catalyzed Picolinamide-Directed Late-Stage Chalcogenation of Tryptophan-Containing Peptides

This report describes the Pd-catalyzed late-stage chalcogenation of tryptophan-containing peptides with disulfides/diselenides in moderate to good yields. It comprises broad substrate scope, functional group diversity, late-stage modification of drug molecules, and various valuable synthetic transfo...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-11, Vol.88 (22), p.15666-15686
Main Authors: Bag, Raghunath, Sharma, Nagendra K.
Format: Article
Language:English
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Summary:This report describes the Pd-catalyzed late-stage chalcogenation of tryptophan-containing peptides with disulfides/diselenides in moderate to good yields. It comprises broad substrate scope, functional group diversity, late-stage modification of drug molecules, and various valuable synthetic transformations, including room temperature easy removal of the picolinamide auxiliary, which could be applicable to tune the structure and function of peptides.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01657