Peroxygenase-Catalyzed Oxyfunctionalization Reactions Promoted by the Complete Oxidation of Methanol
Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need a balanced provision of hydrogen peroxide to achieve high catalytic activity while minimizing oxidative inactivation. Herein, we report an e...
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| Published in | Angewandte Chemie (International ed.) Vol. 55; no. 2; pp. 798 - 801 |
|---|---|
| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
11.01.2016
Wiley WILEY‐VCH Verlag Wiley Subscription Services, Inc |
| Edition | International ed. in English |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1433-7851 1521-3773 1521-3773 |
| DOI | 10.1002/anie.201507881 |
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| Abstract | Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need a balanced provision of hydrogen peroxide to achieve high catalytic activity while minimizing oxidative inactivation. Herein, we report an enzymatic cascade process that employs methanol as a sacrificial electron donor for the reductive activation of molecular oxygen. Full oxidation of methanol is achieved, generating three equivalents of hydrogen peroxide that can be used completely for the stereoselective hydroxylation of ethylbenzene as a model reaction. Overall we propose and demonstrate an atom‐efficient and easily applicable alternative to established hydrogen peroxide generation methods, which enables the efficient use of peroxygenases for oxyfunctionalization reactions.
Fueled by methanol: Peroxygenases catalyze stereoselective oxyfunctionalizations by utilizing H2O2. To efficiently generate this oxidant in situ, a new enzymatic cascade process for the reductive activation of molecular oxygen with methanol as a stoichiometric reductant has been developed. This system was applied to the stereoselective hydroxylation of ethylbenzene to (R)‐1‐phenylethanol. |
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| AbstractList | Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need a balanced provision of hydrogen peroxide to achieve high catalytic activity while minimizing oxidative inactivation. Herein, we report an enzymatic cascade process that employs methanol as a sacrificial electron donor for the reductive activation of molecular oxygen. Full oxidation of methanol is achieved, generating three equivalents of hydrogen peroxide that can be used completely for the stereoselective hydroxylation of ethylbenzene as a model reaction. Overall we propose and demonstrate an atom‐efficient and easily applicable alternative to established hydrogen peroxide generation methods, which enables the efficient use of peroxygenases for oxyfunctionalization reactions.
Fueled by methanol: Peroxygenases catalyze stereoselective oxyfunctionalizations by utilizing H2O2. To efficiently generate this oxidant in situ, a new enzymatic cascade process for the reductive activation of molecular oxygen with methanol as a stoichiometric reductant has been developed. This system was applied to the stereoselective hydroxylation of ethylbenzene to (R)‐1‐phenylethanol. Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need a balanced provision of hydrogen peroxide to achieve high catalytic activity while minimizing oxidative inactivation. Herein, we report an enzymatic cascade process that employs methanol as a sacrificial electron donor for the reductive activation of molecular oxygen. Full oxidation of methanol is achieved, generating three equivalents of hydrogen peroxide that can be used completely for the stereoselective hydroxylation of ethylbenzene as a model reaction. Overall we propose and demonstrate an atom-efficient and easily applicable alternative to established hydrogen peroxide generation methods, which enables the efficient use of peroxygenases for oxyfunctionalization reactions. Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need a balanced provision of hydrogen peroxide to achieve high catalytic activity while minimizing oxidative inactivation. Herein, we report an enzymatic cascade process that employs methanol as a sacrificial electron donor for the reductive activation of molecular oxygen. Full oxidation of methanol is achieved, generating three equivalents of hydrogen peroxide that can be used completely for the stereoselective hydroxylation of ethylbenzene as a model reaction. Overall we propose and demonstrate an atom-efficient and easily applicable alternative to established hydrogen peroxide generation methods, which enables the efficient use of peroxygenases for oxyfunctionalization reactions.Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need a balanced provision of hydrogen peroxide to achieve high catalytic activity while minimizing oxidative inactivation. Herein, we report an enzymatic cascade process that employs methanol as a sacrificial electron donor for the reductive activation of molecular oxygen. Full oxidation of methanol is achieved, generating three equivalents of hydrogen peroxide that can be used completely for the stereoselective hydroxylation of ethylbenzene as a model reaction. Overall we propose and demonstrate an atom-efficient and easily applicable alternative to established hydrogen peroxide generation methods, which enables the efficient use of peroxygenases for oxyfunctionalization reactions. |
| Author | Hollmann, Frank Hofrichter, Martin van Berkel, Willem J. H. Fernández-Fueyo, Elena Ni, Yan Yanase, Hideshi Ullrich, René Baraibar, Alvaro Gomez Alcalde, Miguel |
| Author_xml | – sequence: 1 givenname: Yan surname: Ni fullname: Ni, Yan organization: Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628BL Delft (The Netherlands) – sequence: 2 givenname: Elena surname: Fernández-Fueyo fullname: Fernández-Fueyo, Elena organization: Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628BL Delft (The Netherlands) – sequence: 3 givenname: Alvaro Gomez surname: Baraibar fullname: Baraibar, Alvaro Gomez organization: Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628BL Delft (The Netherlands) – sequence: 4 givenname: René surname: Ullrich fullname: Ullrich, René organization: Department of Bio- and Environmental Science, Technical University of Dresden-International Institute Zittau, 02763 Zittau (Germany) – sequence: 5 givenname: Martin surname: Hofrichter fullname: Hofrichter, Martin organization: Department of Bio- and Environmental Science, Technical University of Dresden-International Institute Zittau, 02763 Zittau (Germany) – sequence: 6 givenname: Hideshi surname: Yanase fullname: Yanase, Hideshi organization: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyamacho-Minami, Tottori, Tottori 680-8552 (Japan) – sequence: 7 givenname: Miguel surname: Alcalde fullname: Alcalde, Miguel organization: Department of Biocatalysis, Institute of Catalysis, CSIC, 28049 Madrid (Spain) – sequence: 8 givenname: Willem J. H. surname: van Berkel fullname: van Berkel, Willem J. H. organization: Laboratory of Biochemistry, Wageningen University, Dreijenlaan 3, 6703 HA Wageningen (The Netherlands) – sequence: 9 givenname: Frank surname: Hollmann fullname: Hollmann, Frank email: f.hollmann@tudelft.nl organization: Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628BL Delft (The Netherlands) |
| BackLink | https://cir.nii.ac.jp/crid/1870020692813690752$$DView record in CiNii https://www.ncbi.nlm.nih.gov/pubmed/26607550$$D View this record in MEDLINE/PubMed |
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| Copyright | 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim Wageningen University & Research |
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| Keywords | oxidation heme proteins hydroxylation hydrogen peroxide peroxygenases |
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| Snippet | Peroxygenases catalyze a broad range of (stereo)selective oxyfunctionalization reactions. However, to access their full catalytic potential, peroxygenases need... |
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| SubjectTerms | Catalysis Catalytic activity Chemical reactions Deactivation Ethylbenzene Heme proteins Hydrogen peroxide Hydroxylation Inactivation Methanol Methanol - chemistry Mixed Function Oxygenases Mixed Function Oxygenases - metabolism Oxidation Oxidation-Reduction Oxygen Peroxygenases |
| Title | Peroxygenase-Catalyzed Oxyfunctionalization Reactions Promoted by the Complete Oxidation of Methanol |
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