Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N-H Carbene Insertions
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Título: | Exporting Metal-Carbene Chemistry to Live Mammalian Cells: Copper-Catalyzed Intracellular Synthesis of Quinoxalines Enabled by N-H Carbene Insertions
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Autor/a: | Gutiérrez Hernández, Sara
Tomás Gamasa, María
Mascareñas Cid, José Luis
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Centro/Departamento: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica
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Palabras chave: | Copper | Bioorthogonal chemistry | Intracellular chemistry | Metal carbenes | Metal catalysis | |
Data: | 2021
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Editor: | Wiley
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Cita bibliográfica: | Angew. Chem. Int. Ed. 2021, 60, 22017–22025
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Resumo: | Implementing catalytic organometallic transformations in living settings can offer unprecedented opportunities in chemical biology and medicine. Unfortunately, the number of biocompatible reactions so far discovered is very limited, and essentially restricted to uncaging processes. Here, we demonstrate the viability of performing metal carbene transfer reactions in live mammalian cells. In particular, we show that copper (II) catalysts can promote the intracellular annulation of alpha-keto diazocarbenes with ortho-amino arylamines, in a process that is initiated by an N-H carbene insertion. The potential of this transformation is underscored by the in cellulo synthesis of a product that alters mitochondrial functions, and by demonstrating cell selective biological responses using targeted copper catalysts. Considering the wide reactivity spectrum of metal carbenes, this work opens the door to significantly expanding the repertoire of life-compatible abiotic reactions |
Versión do editor: | https://doi.org/10.1002/anie.202108899 |
URI: | http://hdl.handle.net/10347/26954
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DOI: | 10.1002/anie.202108899 |
ISSN: | 1433-7851
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E-ISSN: | 1521-3773
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Dereitos: | © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made Attribution-NonCommercial-NoDerivatives 4.0 Internacional
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