Decarboxylative Peptide Macrocyclization through Photoredox Catalysis
| Autor: | Jennifer X. Qiao, Michael M. Miller, Robert M. Borzilleri, Michael A. Poss, Joseph Carpenter, David W. C. MacMillan, Stefan J. McCarver, Martin D. Eastgate |
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| Rok vydání: | 2016 |
| Předmět: |
Macromolecular Substances
Bioactive molecules Context (language use) Peptide 010402 general chemistry Decarboxylation 01 natural sciences Article Catalysis Organic chemistry chemistry.chemical_classification Molecular Structure Chemistry 010405 organic chemistry Photoredox catalysis General Chemistry General Medicine Photochemical Processes Combinatorial chemistry Cyclic peptide Amino acid 0104 chemical sciences Somatostatin Analogue Cyclization Peptides Oxidation-Reduction |
| Zdroj: | Angewandte Chemie. 129:746-750 |
| ISSN: | 1521-3757 0044-8249 |
| DOI: | 10.1002/ange.201608207 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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