Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways

Research output: Contribution to journal/Conference contribution in journal/Contribution to newspaperJournal articleResearchpeer-review

DOI

  • Wolfgang Kroutil, Universität Graz
  • ,
  • Susanne Reischauer, Max Planck Institute of Colloids and Interfaces
  • ,
  • Sarah Bierbaumer, Universität Graz
  • ,
  • Christoph K. Winkler, Universität Graz
  • ,
  • Alba Diaz-Rodriguez, GlaxoSmithKline
  • ,
  • Lee J. Edwards, GlaxoSmithKline
  • ,
  • Selin Kara
  • Tamara Mielke, University of York
  • ,
  • Jared Cartwright, University of York
  • ,
  • Gideon Grogan, University of York
  • ,
  • Bartholomaeus Pieber , Max Planck Institute of Colloids and Interfaces
  • ,
  • Luca Schmermund, University of Graz

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 % ee). 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 % ee).

Original languageEnglish
JournalAngewandte Chemie
Volume60
Issue13
Pages (from-to)6965-6969
Number of pages5
ISSN0044-8249
DOIs
Publication statusPublished - Mar 2021

    Research areas

  • C−H activation, carbon nitrides, chromoselectivity, photobiocatalysis, unspecific peroxygenases

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