Details
| Original language | English |
|---|---|
| Pages (from-to) | 3093-3100 |
| Number of pages | 8 |
| Journal | CHEMCATCHEM |
| Volume | 11 |
| Issue number | 13 |
| Early online date | 6 Jun 2019 |
| Publication status | Published - 4 Jul 2019 |
Abstract
Photoenzymatic cascades can be used for selective oxygenation of C−H-Bonds under mild conditions circumventing the hydrogen peroxide mediated peroxygenase inactivation via in situ H 2O 2 generation. Here, we report the “on demand” production of hydrogen peroxide via methanol assisted reduction of molecular oxygen using UV-illuminated titanium dioxide (Aeroxide P25) combined with the enantioselective hydroxylation of ethylbenzene to (R)-1-phenylethanole catalyzed by the Unspecific Peroxygenase from Agrocybe Aegerita. For the application of the system it is important to understand the influence of the reaction parameters to be able to optimize the system. Therefore, we systematically investigated product formation and enzyme inactivation as well as ROS formation (H 2O 2, .OH and .O 2 −) applying different light intensities and temperatures. As a result, Turnover Numbers up to 220 000, photonic efficiencies up to 13.6 % and production rates up to 0.9 mM h −1 were achieved.
Keywords
- enzyme inactivation, hydrogen peroxide, light intensity, peroxygenases, photocatalysis
ASJC Scopus subject areas
- Chemical Engineering(all)
- Catalysis
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
- Chemistry(all)
- Inorganic Chemistry
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In: CHEMCATCHEM, Vol. 11, No. 13, 04.07.2019, p. 3093-3100.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Photoenzymatic Hydroxylation of Ethylbenzene Catalyzed by Unspecific Peroxygenase
T2 - Origin of Enzyme Inactivation and the Impact of Light Intensity and Temperature
AU - Burek, Bastien O.
AU - Boer, Sabrina R. de
AU - Tieves, Florian
AU - Zhang, Wuyuan
AU - Schie, Morten van
AU - Bormann, Sebastian
AU - Alcalde, Miguel
AU - Holtmann, Dirk
AU - Hollmann, Frank
AU - Bahnemann, Detlef
AU - Bloh, Jonathan Z.
N1 - Funding information: SRdB, BOB and JZB gratefully acknowledge financial support by German Research Foundation (DFG, Grant No: BL 1425/1-1). FH thanks the European Research Council (ERC Consolidator Grant No. 648026) for financial support.
PY - 2019/7/4
Y1 - 2019/7/4
N2 - Photoenzymatic cascades can be used for selective oxygenation of C−H-Bonds under mild conditions circumventing the hydrogen peroxide mediated peroxygenase inactivation via in situ H 2O 2 generation. Here, we report the “on demand” production of hydrogen peroxide via methanol assisted reduction of molecular oxygen using UV-illuminated titanium dioxide (Aeroxide P25) combined with the enantioselective hydroxylation of ethylbenzene to (R)-1-phenylethanole catalyzed by the Unspecific Peroxygenase from Agrocybe Aegerita. For the application of the system it is important to understand the influence of the reaction parameters to be able to optimize the system. Therefore, we systematically investigated product formation and enzyme inactivation as well as ROS formation (H 2O 2, .OH and .O 2 −) applying different light intensities and temperatures. As a result, Turnover Numbers up to 220 000, photonic efficiencies up to 13.6 % and production rates up to 0.9 mM h −1 were achieved.
AB - Photoenzymatic cascades can be used for selective oxygenation of C−H-Bonds under mild conditions circumventing the hydrogen peroxide mediated peroxygenase inactivation via in situ H 2O 2 generation. Here, we report the “on demand” production of hydrogen peroxide via methanol assisted reduction of molecular oxygen using UV-illuminated titanium dioxide (Aeroxide P25) combined with the enantioselective hydroxylation of ethylbenzene to (R)-1-phenylethanole catalyzed by the Unspecific Peroxygenase from Agrocybe Aegerita. For the application of the system it is important to understand the influence of the reaction parameters to be able to optimize the system. Therefore, we systematically investigated product formation and enzyme inactivation as well as ROS formation (H 2O 2, .OH and .O 2 −) applying different light intensities and temperatures. As a result, Turnover Numbers up to 220 000, photonic efficiencies up to 13.6 % and production rates up to 0.9 mM h −1 were achieved.
KW - enzyme inactivation
KW - hydrogen peroxide
KW - light intensity
KW - peroxygenases
KW - photocatalysis
UR - http://www.scopus.com/inward/record.url?scp=85067414938&partnerID=8YFLogxK
U2 - 10.1002/cctc.201900610
DO - 10.1002/cctc.201900610
M3 - Article
VL - 11
SP - 3093
EP - 3100
JO - CHEMCATCHEM
JF - CHEMCATCHEM
SN - 1867-3880
IS - 13
ER -