Efficient and Selective Carboligation with Whole‐Cell Biocatalysts in Pickering Emulsion

Pickering emulsions (PEs) are particle‐stabilized multiphase systems with promising features for synthetic applications. Described here is a novel, simplified set‐up employing catalytically active whole cells for simultaneous emulsion stabilization and synthetic reaction. In the stereoselective carb...

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Bibliographic Details
Published in:Angewandte Chemie 2019-09, Vol.131 (37), p.13094-13097
Main Authors: Röllig, Robert, Plikat, Christoph, Ansorge‐Schumacher, Marion B.
Format: Article
Language:English
Subjects:
Aquatic environment
Benzaldehyde
Benzoin
Biocatalysts
Biokatalyse
Carboligation
Catalysis
Chemistry
E coli
Emulsionen
Emulsions
Hydrophobicity
Silicon
Silicones
Stereoselectivity
Substrates
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Summary:Pickering emulsions (PEs) are particle‐stabilized multiphase systems with promising features for synthetic applications. Described here is a novel, simplified set‐up employing catalytically active whole cells for simultaneous emulsion stabilization and synthetic reaction. In the stereoselective carboligation of benzaldehyde to (R)‐benzoin catalyzed by a benzaldehyde lyase in E. coli, the set‐up yielded maximum substrate conversion within very short time, while economizing material demand and waste. Formation and activity of freshly produced PEs were enhanced when the catalytic whole cells were covered with hydrophobic silicone prior to PE formation. Benchmarked against other easy‐to‐handle whole‐cell biocatalysts in pure organic solvent, neat substrate, an aqueous emulsion in substrate, and a micro‐aquatic system, respectively, the cell‐stabilized PE outperformed all other systems by far. Einfach, aber effizient: Katalytisch aktive Ganzzellen, die Pickering‐Emulsionen stabilisieren, bieten ein einfaches und hocheffizientes System zur Multiphasen‐Biokatalyse für die Synthese. Eine stereoselektive Carboligation von Benzaldehyd zu (R)‐Benzoin mithilfe einer Benzaldehyd‐Lyase in E. coli ergab so einen maximalen Substratumsatz in sehr kurzer Zeit bei wirtschaftlichem Materialbedarf und ‐abfall.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201907209