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  Chromoselective photocatalysis enables stereocomplementary biocatalytic pathways

Kroutil, W., 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. doi:10.1002/anie.202100164.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0007-ABBC-5 Version Permalink: http://hdl.handle.net/21.11116/0000-0007-E017-2
Genre: Journal Article

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 Creators:
Kroutil, Wolfgang, Author
Reischauer, Susanne1, Author              
Bierbaumer, Sarah, Author
Winkler, Christoph K., Author
Diaz-Rodriguez, Alba, Author
Edwards, Lee J, Author
Kara, Selin, Author
Mielke, Tamara, Author
Cartwright, Jared, Author
Grogan, Gideon, Author
Pieber, Bartholomäus1, Author              
Schmermund, Luca, Author
Affiliations:
1Bartholomäus Pieber, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_2522692              

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Free keywords: Photobiocatalysis; C-H activation; unspecific peroxygenases; Carbon Nitrides Photocatalysts; carbon nitrides; chromoselectivity
 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 ).

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Language(s): eng - English
 Dates: 2021-02-02
 Publication Status: Published online
 Pages: -
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 Table of Contents: -
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ISSN: 1433-7851

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Title: Angewandte Chemie
  Abbreviation : Angew. Chem.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ISSN: 0044-8249

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Title: ChemRxiv
Source Genre: Journal
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Publ. Info: Washington, Frankfurt am Main, Cambridge : ACS, GDCh, RSC
Pages: - Volume / Issue: - Sequence Number: 13521527 Start / End Page: - Identifier: ZDB: 2949094-7