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Decarboxylative Peptide Macrocyclization through Photoredox Catalysis.


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 ?-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.

SUBMITTER: McCarver SJ 

PROVIDER: S-EPMC5225041 | biostudies-literature | 2017 Jan

REPOSITORIES: biostudies-literature

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Decarboxylative Peptide Macrocyclization through Photoredox Catalysis.

McCarver Stefan J SJ   Qiao Jennifer X JX   Carpenter Joseph J   Borzilleri Robert M RM   Poss Michael A MA   Eastgate Martin D MD   Miller Michael M MM   MacMillan David W C DW  

Angewandte Chemie (International ed. in English) 20161117 3


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 molecu  ...[more]

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