Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways

Luca Schmermund, Susanne Reischauer, Sarah Bierbaumer, Christoph Winkler, Alba Diaz-Rodriguez, Lee Edwards, Selin Kara, Tamara Mielke, J.L. Cartwright, Gideon James Grogan, Bartholomaus Pieber, Wolfgang Kroutil

Research output: Contribution to journalArticlepeer-review


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.).
Original languageEnglish
JournalAngewandte Chemie International Edition
Issue number13
Early online date2 Feb 2021
Publication statusPublished - 22 Mar 2022

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