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Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways

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Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways. / Kroutil, Wolfgang; Reischauer, Susanne; Bierbaumer, Sarah; Winkler, Christoph K.; Diaz-Rodriguez, Alba; J. Edwards, Lee; Kara, Selin; Mielke, Tamara; Cartwright, Jared; Grogan, Gideon; Pieber , Bartholomaeus; Schmermund, Luca .

In: Angewandte Chemie, Vol. 60, No. 13, 03.2021, p. 6965-6969.

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

Harvard

Kroutil, W, Reischauer, S, Bierbaumer, S, Winkler, CK, Diaz-Rodriguez, A, J. Edwards, L, Kara, S, Mielke, T, Cartwright, J, Grogan, G, Pieber , B & Schmermund, L 2021, 'Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways', Angewandte Chemie, vol. 60, no. 13, pp. 6965-6969. https://doi.org/10.1002/anie.202100164

APA

Kroutil, W., Reischauer, S., Bierbaumer, S., Winkler, C. K., Diaz-Rodriguez, A., J. Edwards, L., Kara, S., Mielke, T., Cartwright, J., Grogan, G., Pieber , B., & Schmermund, L. (2021). Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways. Angewandte Chemie, 60(13), 6965-6969. https://doi.org/10.1002/anie.202100164

CBE

Kroutil W, Reischauer S, Bierbaumer S, Winkler CK, Diaz-Rodriguez A, J. Edwards L, Kara S, Mielke T, Cartwright J, Grogan G, Pieber B, Schmermund L. 2021. Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways. Angewandte Chemie. 60(13):6965-6969. https://doi.org/10.1002/anie.202100164

MLA

Vancouver

Kroutil W, Reischauer S, Bierbaumer S, Winkler CK, Diaz-Rodriguez A, J. Edwards L et al. Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways. Angewandte Chemie. 2021 Mar;60(13):6965-6969. https://doi.org/10.1002/anie.202100164

Author

Kroutil, Wolfgang ; Reischauer, Susanne ; Bierbaumer, Sarah ; Winkler, Christoph K. ; Diaz-Rodriguez, Alba ; J. Edwards, Lee ; Kara, Selin ; Mielke, Tamara ; Cartwright, Jared ; Grogan, Gideon ; Pieber , Bartholomaeus ; Schmermund, Luca . / Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways. In: Angewandte Chemie. 2021 ; Vol. 60, No. 13. pp. 6965-6969.

Bibtex

@article{2e70b42fb61a45358573029fc1148e8c,
title = "Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways",
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 % 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).",
keywords = "C−H activation, carbon nitrides, chromoselectivity, photobiocatalysis, unspecific peroxygenases",
author = "Wolfgang Kroutil and Susanne Reischauer and Sarah Bierbaumer and Winkler, {Christoph K.} and Alba Diaz-Rodriguez and {J. Edwards}, Lee and Selin Kara and Tamara Mielke and Jared Cartwright and Gideon Grogan and Bartholomaeus Pieber and Luca Schmermund",
year = "2021",
month = mar,
doi = "10.1002/anie.202100164",
language = "English",
volume = "60",
pages = "6965--6969",
journal = "Angewandte Chemie",
issn = "0044-8249",
publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",
number = "13",

}

RIS

TY - JOUR

T1 - Chromoselective Photocatalysis Enables Stereocomplementary Biocatalytic Pathways

AU - Kroutil, Wolfgang

AU - Reischauer, Susanne

AU - Bierbaumer, Sarah

AU - Winkler, Christoph K.

AU - Diaz-Rodriguez, Alba

AU - J. Edwards, Lee

AU - Kara, Selin

AU - Mielke, Tamara

AU - Cartwright, Jared

AU - Grogan, Gideon

AU - Pieber , Bartholomaeus

AU - Schmermund, Luca

PY - 2021/3

Y1 - 2021/3

N2 - 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).

AB - 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).

KW - C−H activation

KW - carbon nitrides

KW - chromoselectivity

KW - photobiocatalysis

KW - unspecific peroxygenases

UR - http://www.scopus.com/inward/record.url?scp=85101618129&partnerID=8YFLogxK

U2 - 10.1002/anie.202100164

DO - 10.1002/anie.202100164

M3 - Journal article

C2 - 33529432

AN - SCOPUS:85101618129

VL - 60

SP - 6965

EP - 6969

JO - Angewandte Chemie

JF - Angewandte Chemie

SN - 0044-8249

IS - 13

ER -