sc8b06715_si_001.pdf (1.53 MB)
Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic Solvents
journal contribution
posted on 2019-02-12, 17:21 authored by Juraj Paris, Aline Telzerow, Nicolás Ríos-Lombardía, Kerstin Steiner, Helmut Schwab, Francisco Morís, Harald Gröger, Javier González-SabínThe 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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enantioselective bioaminationchemoenzymatic cascadeATADESbuffer mixturesDeep Eutectic Solventsbiaryl aminessolubilizing propertiesEX -ωTAEnantioselective One-Pot SynthesisSuzuki reaction sequentiallyEnzyme Catalysis200 mM loadingBiaryl-Substituted Amines25 mMreaction mediumExophiala xenobioticaamine transaminasesmetal-catalyzed step
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