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Synfacts 2022; 18(01): 0101
DOI: 10.1055/s-0041-1737499
Peptide Chemistry

Palladium-Catalyzed Multiple S-Arylation for the Synthesis of Macrocyclic Peptides

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
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.
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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.


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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.


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Publication History

Article published online:
17 December 2021

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