Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Juraj Paris; Aline Telzerow; Nicolás Ríos-Lombardía; Kerstin Steiner; Helmut Schwab; Francisco Morís; Harald Gröger; Javier González-Sabín

doi:10.1021/acssuschemeng.8b06715

Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Juraj Paris, Aline Telzerow, Nicolás Ríos-Lombardía, Kerstin Steiner, Helmut Schwab, Francisco Morís, Harald Gröger^*, Javier González-Sabín

^*Corresponding author for this work

Institute of Molecular Biotechnology (6550)

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

Abstract

The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-ωTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.

Original language	English
Pages (from-to)	5486-5493
Number of pages	8
Journal	ACS Sustainable Chemistry and Engineering
Volume	7
Issue number	5
DOIs	https://doi.org/10.1021/acssuschemeng.8b06715
Publication status	Published - 4 Mar 2019

Keywords

Amines
Asymmetric synthesis
Biocatalysis
Deep eutectic solvents
Palladium catalysis
Suzuki cross-coupling reaction

ASJC Scopus subject areas

General Chemistry
Environmental Chemistry
General Chemical Engineering
Renewable Energy, Sustainability and the Environment

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acssuschemeng.8b06715

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Paris, J, Telzerow, A, Ríos-Lombardía, N, Steiner, K, Schwab, H, Morís, F, Gröger, H & González-Sabín, J 2019, 'Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents', ACS Sustainable Chemistry and Engineering, vol. 7, no. 5, pp. 5486-5493. https://doi.org/10.1021/acssuschemeng.8b06715

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abstract = "The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-ωTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.",

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AU - Paris, Juraj

AU - Telzerow, Aline

AU - Ríos-Lombardía, Nicolás

AU - Steiner, Kerstin

AU - Schwab, Helmut

AU - Morís, Francisco

AU - Gröger, Harald

AU - González-Sabín, Javier

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AB - The first application of Deep Eutectic Solvents (DESs) in asymmetric bioamination of ketones has been accomplished. The amine transaminases (ATAs) turned out to be particularly stable in DES-buffer mixtures at a percentage of up to 75% (w/w) neoteric solvent. Moreover, this reaction medium was used to perform a chemoenzymatic cascade toward biaryl amines by coupling a Suzuki reaction sequentially with an enantioselective bioamination catalyzed by the recently discovered ATA from Exophiala xenobiotica (EX-ωTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.

KW - Amines

KW - Asymmetric synthesis

KW - Biocatalysis

KW - Deep eutectic solvents

KW - Palladium catalysis

KW - Suzuki cross-coupling reaction

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JO - ACS Sustainable Chemistry and Engineering

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ER -

Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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