Published February 12, 2019 | Version Accepted
Journal article Open

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

Creators

  • 1. Bielefeld University
  • 2. Graz University of Technology
  • 3. Entrechem SL

Description

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‑wTA). The solubilizing properties of DESs enabled the metal-catalyzed step at 200 mM loading of substrate and the subsequent biotransformation at 25 mM.

Notes

The authors acknowledge generous support from the European Union's Horizon 2020 MSCA ITN-EID program under grant agreement No 634200 (Project BIOCASCADES). The authors also thank Dr. Wolfgang Kroutil for the generous gift of the amine transaminases Cv, ArS, ArR and ArRmut11.

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Enantioselective One-Pot Synthesis of Biaryl-Substituted Amines.pdf

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Additional details

Related works

Cites
10.1021/acssuschemeng.8b06715 (DOI)

Funding

BIOCASCADES – BIOCASCADES- Sustainable and Scalable Biocatalytic Cascade Reactions Training Network 634200
European Commission