Peptide macrocyclization by transition metal catalysis

Chemical Society Reviews
Daniel G RiveraErik V Van der Eycken

Abstract

Peptide macrocyclization has traditionally relied on lactam, lactone and disulfide bond-forming reactions that aim at introducing conformational constraints into small peptide sequences. With the advent of ruthenium-catalyzed ring-closing metathesis and copper-catalyzed alkyne-azide cycloaddition, peptide chemists embraced transition metal catalysis as a powerful macrocyclization tool with relevant applications in chemical biological and peptide drug discovery. This article provides a comprehensive overview of the reactivity and methodological diversification of metal-catalyzed peptide macrocyclization as a special class of late-stage peptide derivatization method. We report the evolution from classic palladium-catalyzed cross-coupling approaches to more modern oxidative versions based on C-H activation, heteroatom alkylation/arylation and annulation processes, in which aspects such as chemoselectivity and diversity generation at the ring-closing moiety became dominant over the last years. The transit from early cycloadditions and alkyne couplings as ring-closing steps to very recent 3d metal-catalyzed macrocyclization methods is highlighted. Similarly, the new trends in decarboxylative radical macrocyclizations and the interpl...Continue Reading

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Citations

Sep 5, 2020·Chemistry : a European Journal·Éric GodinShawn K Collins
Sep 12, 2020·Chemistry : a European Journal·Laetitia RaynalChristopher D Spicer
Oct 30, 2020·Chemical Communications : Chem Comm·Bei-Bei ZhanBing-Feng Shi
Dec 5, 2020·Chemistry : a European Journal·Samuel OforiSamuel G Awuah
May 6, 2021·Chembiochem : a European Journal of Chemical Biology·Jiang LiuQing Zhu
May 13, 2021·Organic & Biomolecular Chemistry·Heather C HayesYu-Hsuan Tsai
May 23, 2021·Bioorganic Chemistry·Manuel G RicardoDaniel G Rivera
Jun 8, 2021·Chemical Science·Marcos San Segundo, Arkaitz Correa
Jul 2, 2021·Chemical Science·Wen WeiLutz Ackermann
Jul 9, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Bishnu Das, Parna Gupta
Jul 3, 2021·Angewandte Chemie·Guillaume ForceDavid Lebœuf
Aug 18, 2021·Inorganic Chemistry·Sailajah GukathasanSamuel G Awuah
Jun 10, 2021·Chemistry : a European Journal·Weijin WangHans Renata
Dec 2, 2020·Organic Letters·Manikantha MaraswamiTeck-Peng Loh
Aug 28, 2021·RSC Medicinal Chemistry·Clément Bechtler, Christina Lamers

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Methods Mentioned

BETA
X-ray
GTPase

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