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C‐Terminal Bioconjugation of Peptides through Photoredox Catalyzed Decarboxylative Alkynylation
Author(s) -
Garreau Marion,
Le Vaillant Franck,
Waser Jerome
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.201901922
Subject(s) - bioconjugation , chemistry , hypervalent molecule , reagent , catalysis , combinatorial chemistry , alkynylation , carboxylic acid , organic chemistry , peptide , amino acid , biochemistry
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.