Chu X,
Shen L,
Li B,
Yang P,
Du C,
Wang X,
He G,
Messaoudi S,
*,
Chen G.
*
University Paris-Saclay, ChÂtenay-Malabry, France and Nankai University, Tianjin,
P. R. of China
Construction of Peptide Macrocycles via Palladium-Catalyzed Multiple S-Arylation:
An Effective Strategy to Expand the Structural Diversity of Cross-Linkers.
Org. Lett. 2021;
23: 8001-8006
DOI:
10.1021/acs.orglett.1c03003
Key words
palladium catalysis - macrocyclization - S-arylation - iodoarenes - cross-linked peptide
macrocycles
Significance
Macrocyclic peptides are highly demanding targets in the field of peptide-drug discovery.
The authors have developed an unprecedented macrocyclization of native peptides containing
cysteine residues by reaction with di- or triiodo(het) arenes with the help of a palladium
catalyst.
Comment
The palladium-catalyzed multiple S-arylation of cysteine residues of unprotected native
peptides with di- or triiodo(het)arenes proceeded smoothly to afford the desired macrocyclic
peptides in good yields. This method is practically simple and is one of the most
powerful methods for the production of cross-linked peptide macrocycles.
