Schmermund, Luca, Reischauer, Susanne, Bierbaumer, Sarah et al. (9 more authors) (2022) Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways. Angewandte Chemie International Edition. ISSN 1433-7851
Abstract
Controlling the selectivity of a chemical reaction with external stimuli is common in thermal processes, but rare in visible light photocatalysis. Here we show that the redox potential of a carbon nitride photocatalyst (CN-OA-m) can be tuned by changing the irradiation wavelength to generate electron holes with different oxidation potentials. This tuning was the key to realizing photochemo-enzymatic cascades that give either the (S)- or the (R)- enantiomer of phenylethanol. In combination with an unspecific peroxygenase from Agrocybe aegerita, green light irradiation of CNOA-m led to the enantioselective hydroxylation of ethylbenzene to (R)-1-phenylethanol (99% e.e.). In contrast, blue light irradiation triggered the photocatalytic oxidation of ethylbenzene to acetophenone, which in turn was enantioselectively reduced with an alcohol dehydrogenase from Rhodococcus ruber to form (S)-1-phenylethanol (93% e.e.).
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 22 Mar 2021 17:50 |
Last Modified: | 19 Oct 2024 00:06 |
Published Version: | https://doi.org/10.1002/anie.202100164 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1002/anie.202100164 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:172458 |