Issue 6, 2017

Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)–H activation

Abstract

Cyclic peptides have attracted increasing attention in recent years due to their ability to inhibit protein–protein interactions. Current strategies to prepare cyclic peptides often rely on functional amino acid side chains or the incorporation of unnatural amino acids, thus limiting their structural diversity. Here, we describe the development of a highly versatile peptide macrocyclization strategy through a palladium-catalyzed C(sp3)–H activation and the synthesis of cyclic peptides featuring unique hydrocarbon linkages between the β-carbon of amino acids and the aromatic side chains of Phe and Trp. We demonstrate that such peptides exhibit improved biological properties compared to their acyclic counterparts. Finally, we applied this method in the synthesis of the natural product celogentin C.

Graphical abstract: Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)–H activation

Supplementary files

Article information

Article type
Edge Article
Submitted
18 12 2016
Accepted
11 4 2017
First published
19 4 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2017,8, 4565-4570

Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)–H activation

J. Tang, Y. He, H. Chen, W. Sheng and H. Wang, Chem. Sci., 2017, 8, 4565 DOI: 10.1039/C6SC05530C

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