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

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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

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Publication details

The article was received on 18 Dec 2016, accepted on 11 Apr 2017 and first published on 19 Apr 2017


Article type: Edge Article
DOI: 10.1039/C6SC05530C
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C6SC05530C

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