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Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways
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 electro...
Autores principales: | , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048449/ https://www.ncbi.nlm.nih.gov/pubmed/33529432 http://dx.doi.org/10.1002/anie.202100164 |
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author | Schmermund, Luca Reischauer, Susanne Bierbaumer, Sarah Winkler, Christoph K. Diaz‐Rodriguez, Alba Edwards, Lee J. Kara, Selin Mielke, Tamara Cartwright, Jared Grogan, Gideon Pieber, Bartholomäus Kroutil, Wolfgang |
author_facet | Schmermund, Luca Reischauer, Susanne Bierbaumer, Sarah Winkler, Christoph K. Diaz‐Rodriguez, Alba Edwards, Lee J. Kara, Selin Mielke, Tamara Cartwright, Jared Grogan, Gideon Pieber, Bartholomäus Kroutil, Wolfgang |
author_sort | Schmermund, Luca |
collection | PubMed |
description | 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). |
format | Online Article Text |
id | pubmed-8048449 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-80484492021-04-16 Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways Schmermund, Luca Reischauer, Susanne Bierbaumer, Sarah Winkler, Christoph K. Diaz‐Rodriguez, Alba Edwards, Lee J. Kara, Selin Mielke, Tamara Cartwright, Jared Grogan, Gideon Pieber, Bartholomäus Kroutil, Wolfgang Angew Chem Int Ed Engl Communications 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). John Wiley and Sons Inc. 2021-02-26 2021-03-22 /pmc/articles/PMC8048449/ /pubmed/33529432 http://dx.doi.org/10.1002/anie.202100164 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Schmermund, Luca Reischauer, Susanne Bierbaumer, Sarah Winkler, Christoph K. Diaz‐Rodriguez, Alba Edwards, Lee J. Kara, Selin Mielke, Tamara Cartwright, Jared Grogan, Gideon Pieber, Bartholomäus Kroutil, Wolfgang Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways |
title | Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways
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title_full | Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways
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title_fullStr | Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways
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title_full_unstemmed | Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways
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title_short | Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways
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title_sort | chromoselective photocatalysis enables stereocomplementary biocatalytic pathways |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8048449/ https://www.ncbi.nlm.nih.gov/pubmed/33529432 http://dx.doi.org/10.1002/anie.202100164 |
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