Decarboxylative Peptide Macrocyclization through Photoredox Catalysis. Issue 3 (17th November 2016)

• Record Type: Journal Article
• Authors: McCarver, Stefan J.; Qiao, Jennifer X.; Carpenter, Joseph; Borzilleri, Robert M.; Poss, Michael A.; Eastgate, Martin D.; Miller, Michael M.; MacMillan, David W. C.
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 3(2017)
• Page Start: 728
• Page End: 732
• Publication Date: 2016-11-17
• Subjects: decarboxylation -- macrocycles -- Michael addition -- peptides -- photoredox catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201608207
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A method for the decarboxylative macrocyclization of peptides bearing N‐terminal Michael acceptors has been developed. This synthetic method enables the efficient synthesis of cyclic peptides containing γ‐amino acids and is tolerant of functionalities present in both natural and non‐proteinogenic amino acids. Linear precursors ranging from 3 to 15 amino acids cyclize effectively under this photoredox method. To demonstrate the preparative utility of this method in the context of bioactive molecules, we synthesized COR‐005, a somatostatin analogue that is currently in clinical trials. Abstract : Oh, take me back to the start : A method for the decarboxylative macrocyclization of peptides bearing N‐terminal Michael acceptors was developed. This photoredox method enables efficient synthesis of cyclic peptides containing γ‐amino acids and is tolerant of functionalities present in natural amino acids. Linear precursors ranging from 3 to 15 amino acids can be effectively cyclized by using this method.