Decarboxylative Peptide Macrocyclization Through Photoredox Catalysis

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2016 Nov 19

PMID 27860140

Citations 32

Authors

Stefan J McCarver

Jennifer X Qiao

Joseph Carpenter

Robert M Borzilleri

Michael A Poss

Martin D Eastgate

Michael M Miller

David W C MacMillan

Affiliations

Soon will be listed here.

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.

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