Enantioselective One-Pot Synthesis of Biaryl-Substituted
Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic
Solvents
Posted on 2019-02-12 - 17:21
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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Paris, Juraj; Telzerow, Aline; Ríos-Lombardía, Nicolás; Steiner, Kerstin; Schwab, Helmut; Morís, Francisco; et al. (2019). Enantioselective One-Pot Synthesis of Biaryl-Substituted
Amines by Combining Palladium and Enzyme Catalysis in Deep Eutectic
Solvents. ACS Publications. Collection. https://doi.org/10.1021/acssuschemeng.8b06715
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AUTHORS (8)
JP
Juraj Paris
AT
Aline Telzerow
NR
Nicolás Ríos-Lombardía
KS
Kerstin Steiner
HS
Helmut Schwab
FM
Francisco Morís
HG
Harald Gröger
JG
Javier González-Sabín
KEYWORDS
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