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From the same journal

Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways

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Author(s)

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

Department/unit(s)

Publication details

JournalAngewandte Chemie International Edition
DateAccepted/In press - 2 Feb 2021
DateE-pub ahead of print (current) - 2 Feb 2021
Early online date2/02/21
Original languageEnglish

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.).

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© 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH

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