Decarboxylative Peptide Macrocyclization through Photoredox Catalysis

Stefan J. McCarver; Jennifer X. Qiao; Joseph Carpenter; Robert M. Borzilleri; Michael A. Poss; Martin D. Eastgate; Michael M. Miller; David W.C. MacMillan

doi:10.1002/anie.201608207

Decarboxylative Peptide Macrocyclization through Photoredox Catalysis

Stefan J. McCarver, Jennifer X. Qiao, Joseph Carpenter, Robert M. Borzilleri, Michael A. Poss, Martin D. Eastgate, Michael M. Miller, David W.C. MacMillan

Research output: Contribution to journal › Article › peer-review

112 Scopus citations

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.

Original language	English (US)
Pages (from-to)	728-732
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	3
DOIs	https://doi.org/10.1002/anie.201608207
State	Published - Jan 16 2017

All Science Journal Classification (ASJC) codes

General Chemistry
Catalysis

Keywords

Michael addition
decarboxylation
macrocycles
peptides
photoredox catalysis

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10.1002/anie.201608207

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title = "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 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.",

keywords = "Michael addition, decarboxylation, macrocycles, peptides, photoredox catalysis",

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T1 - Decarboxylative Peptide Macrocyclization through Photoredox Catalysis

AU - McCarver, Stefan J.

AU - Qiao, Jennifer X.

AU - Carpenter, Joseph

AU - Borzilleri, Robert M.

AU - Poss, Michael A.

AU - Eastgate, Martin D.

AU - Miller, Michael M.

AU - MacMillan, David W.C.

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AB - 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.

KW - Michael addition

KW - decarboxylation

KW - macrocycles

KW - peptides

KW - photoredox catalysis

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Decarboxylative Peptide Macrocyclization through Photoredox Catalysis

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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