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Journal Article

Chromoselective photocatalysis enables stereocomplementary biocatalytic pathways

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Reischauer,  Susanne
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Pieber,  Bartholomäus
Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Schmermund, L., Reischauer, S., Bierbaumer, S., Winkler, C. K., Diaz-Rodriguez, A., Edwards, L. J., et al. (2021). Chromoselective photocatalysis enables stereocomplementary biocatalytic pathways. Angewandte Chemie International Edition, 60(13), 6965-6969. doi:10.1002/anie.202100164.


Cite as: http://hdl.handle.net/21.11116/0000-0007-ABBC-5
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 photo‐chemo‐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 CN‐OA‐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 ).