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Synfacts 2025; 21(02): 207
DOI: 10.1055/a-2497-0651
Peptide Chemistry

Palladium-Catalyzed Late-Stage Macrocyclization for the Synthesis of Cyclophane-Braced Glycopeptides

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna 
Bazzi S, Mohamed AH, Ryzhakov D, Ghouilem J, Beniddir MA, Gandon V *, Messaoudi S *. Université Paris-Saclay and Institut Polytechnique de Paris, Palaiseau, France
Diastereoselective Anomeric C(sp3)–H Cyclization Towards the Design of New Cyclophane-Braced Glycopeptides.

Angew. Chem. Int. Ed. 2024;
DOI: 10.1002/anie.202418057
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Keywords

late-stage functionalization - palladium catalysis - macrocyclization - glycopeptides

Significance

Macrocyclic peptides have gained tremendous attention in peptide drug discovery. In this article, the authors have developed a palladium-catalyzed macrocyclization by selective C(sp3)–H arylation of the anomeric bonds for the synthesis of cyclophane-braced glycopeptides.


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Comment

A series of macrocyclic cyclophane-braced glycopeptides has been synthesized in good to moderate yields by a palladium-catalyzed site-selective anomeric C(sp3)–H cyclization approach. This protocol showcases the efficiency of a palladium-catalyzed C–H activation strategy for the synthesis of unnatural cyclic peptides.


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Publication History

Article published online:
28 January 2025

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