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Decarboxylative Peptide Macrocyclization through Photoredox Catalysis
Author(s) -
McCarver Stefan J.,
Qiao Jennifer X.,
Carpenter Joseph,
Borzilleri Robert M.,
Poss Michael A.,
Eastgate Martin D.,
Miller Michael M.,
MacMillan David W. C.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201608207
Subject(s) - amino acid , chemistry , peptide , photoredox catalysis , context (archaeology) , combinatorial chemistry , molecule , somatostatin , stereochemistry , catalysis , organic chemistry , biochemistry , biology , paleontology , photocatalysis , neuroscience
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.