C-Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation

We report the first decarboxylative alkynylation of the C-terminus of peptides starting from free carboxylic acids. The reaction is fast, metal-free, and proceeds cleanly to afford alkynylated peptides with a broad tolerance for the C-terminal amino acid. By the use of hypervalent iodine reagents, the introduction of a broad range of functional groups was successful. C-terminal selectivity was achieved by differentiation of the oxidation potentials of the carboxylic acids based on the use of fine-tuned organic dyes.


Published in:
Angewandte Chemie-International Edition, 58, 24, 8182-8186
Year:
Jun 11 2019
Publisher:
Weinheim, WILEY-V C H VERLAG GMBH
ISSN:
1433-7851
1521-3773
Keywords:
Laboratories:




 Record created 2019-07-20, last modified 2019-07-27


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