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

Chemistry(all)
Environmental Chemistry
Chemical Engineering(all)
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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doi = "10.1021/acssuschemeng.8b06715",

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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

PY - 2019/3/4

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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 & 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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