Backbone-Enabled Directional Peptide Macrocyclization through Late-Stage Palladium-Catalyzed δ-C(sp2 )-H Olefination

Angewandte Chemie
Zengbing BaiHuan Wang

Abstract

C-H activation methods for peptide macrocyclization have the potential to provide peptidomimetics and cyclic peptides with expanded structural diversity. Now, a highly versatile peptide macrocyclization strategy via late-stage palladium-catalyzed δ-C(sp2 )-H olefination of phenylalanine residues has been developed. This method utilizes peptide backbone amides as internal directing groups and allows facile macrocyclization of peptides in the N-to-C direction. Combined with the previously developed β-C(sp3 )-H arylation method for peptide macrocyclization in the C-to-N direction, a pair of palladium-catalyzed reactions were obtained that are directionally orthogonal, and the first example of one-pot synthesis of bicyclic peptides via Pd-catalyzed β-C(sp3 )-H and δ-C(sp2 )-H activation is demonstrated.

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Citations

Mar 7, 2020·Chemical Society Reviews·Daniel G RiveraErik V Van der Eycken
Feb 27, 2020·Organic & Biomolecular Chemistry·Saumitra Sengupta, Goverdhan Mehta
Aug 31, 2019·Organic & Biomolecular Chemistry·Saumitra Sengupta, Srinivasan Chandrasekaran
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Aug 17, 2020·Chemical Reviews·Xiang LiHong-Gang Hu
May 24, 2019·Journal of the American Chemical Society·Bo LiGong Chen
Nov 20, 2018·Bioconjugate Chemistry·Bryan P SutherlandChristopher J Kloxin
Aug 28, 2021·RSC Medicinal Chemistry·Clément Bechtler, Christina Lamers

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