Expanding the Spectrum of Light-Driven Peroxygenase Reactions

Willot, Sébastien J.‐P.; Fernández‐Fueyo, Elena; Tieves, Florian; Pesic, Milja; Alcalde, Miguel; Arends, Isabel W. C. E.; Park, Chan Beum; Hollmann, Frank

doi:10.1021/acscatal.8b03752

Cited by 69 publications

(58 citation statements)

References 33 publications

(56 reference statements)

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“…Many strategies are known for a H 2 O 2 supply in adequate concentrations, especially in situ generation by reduction of molecular oxygen is often applied e. g. via chemical, enzymatic, electrochemical or photochemical approaches to alleviate the instability issue, see Table S4 for a detailed comparison of the methods on the example of Aae UPO catalyzed hydroxylation of ethylbenzene.…”

Section: Introductionmentioning

confidence: 99%

“…[20] This is particularly hampered by the instability of UPOs against their own co-substrate H 2 O 2 . [7,21] Many strategies are known for a H 2 O 2 supply in adequate concentrations, especially in situ generation by reduction of molecular oxygen is often applied e. g. via chemical, [22,23] enzymatic, [24][25][26][27][28][29] electrochemical [30][31][32][33][34][35][36] or photochemical [37][38][39][40][41][42][43][44][45] approaches to alleviate the instability issue, see Table S4 for a detailed comparison of the methods on the example of AaeUPO catalyzed hydroxylation of ethylbenzene.…”

Section: Introductionmentioning

confidence: 99%

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Photoenzymatic Hydroxylation of Ethylbenzene Catalyzed by Unspecific Peroxygenase: Origin of Enzyme Inactivation and the Impact of Light Intensity and Temperature

et al. 2019

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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 H2O2 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 (H2O2, .OH and .O2−) 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.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoenzymatic Hydroxylation of Ethylbenzene Catalyzed by Unspecific Peroxygenase: Origin of Enzyme Inactivation and the Impact of Light Intensity and Temperature

et al. 2019

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“…A number of strategies for light-driven generation of ROS species to fuel the catalysis of P450 enzymes, as opposed to direct electron transfer from a photosensitizer, have also been detailed elsewhere [18]. This strategy has been used to fuel hydroxylation reactions of both P450 and peroxygenase enzymes [90,91]. Using a water oxidation photocatalyst to generate H 2 O 2 can renewably fuel peroxygenase reactivity, opening another route for light energy and enzymatic catalysis to be combined and scaled up [90].…”

Section: Figmentioning

confidence: 99%

Light‐driven catalysis with engineered enzymes and biomimetic systems

Edwards

Bren

2020

Biotech and App Biochem

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Efforts to drive catalytic reactions with light, inspired by natural processes like photosynthesis, have a long history and have seen significant recent growth. Successfully engineering systems using biomolecular and bioinspired catalysts to carry out light‐driven chemical reactions capitalizes on advantages offered from the fields of biocatalysis and photocatalysis. In particular, driving reactions under mild conditions and in water, in which enzymes are operative, using sunlight as a renewable energy source yield environmentally friendly systems. Furthermore, using enzymes and bioinspired systems can take advantage of the high efficiency and specificity of biocatalysts. There are many challenges to overcome to fully capitalize on the potential of light‐driven biocatalysis. In this mini‐review, we discuss examples of enzymes and engineered biomolecular catalysts that are activated via electron transfer from a photosensitizer in a photocatalytic system. We place an emphasis on selected forefront chemical reactions of high interest, including CH oxidation, proton reduction, water oxidation, CO2 reduction, and N2 reduction.

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“…In a recent contribution by the Hollmann group, various acridine photocatalysts such as phenosafranine ( 21 b ) were used for the photochemical oxidation of NADH ( 13 a ), yielding H 2 O 2 from oxygen for Aae UPO oxygenation catalysis. In an enzymatic relay system, the formate dehydrogenase from Candida boidinii ( Cb FDH) serves as a mediator for hydride transfer from formate ( 29 ) to NAD + ( 12 a , Table , entry 24).…”

Section: Photo‐biocatalysis By Application Of Isolated Enzymes or Celmentioning

confidence: 99%

Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes

Seel

Gulder

2019

ChemBioChem

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Enzymes catalyze a plethora of highly specific transformations under mild and environmentally benign reaction conditions. Their fascinating performances attest to high synthetic potential that is often hampered by operational obstacles such as in vitro cofactor supply and regeneration. Exploiting light and combining it with biocatalysis not only helps in overcoming these drawbacks, but the fruitful liaison of these two fields of “green chemistry” also offers opportunities to unlock new synthetic reactivities. In this review we provide an overview of the wide variety of photo‐biocatalysis, ranging from the photochemical delivery of electrons required in redox biocatalysis and photochemical cofactor and reagent (re)generation to direct photoactivation of enzymes enabling reactions unknown in nature. We highlight synthetically relevant transformations such as asymmetric reactions facilitated by the combination of light as energy source and enzymes’ catalytic power.

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Expanding the Spectrum of Light-Driven Peroxygenase Reactions

Cited by 69 publications

References 33 publications

Photoenzymatic Hydroxylation of Ethylbenzene Catalyzed by Unspecific Peroxygenase: Origin of Enzyme Inactivation and the Impact of Light Intensity and Temperature

Photoenzymatic Hydroxylation of Ethylbenzene Catalyzed by Unspecific Peroxygenase: Origin of Enzyme Inactivation and the Impact of Light Intensity and Temperature

Light‐driven catalysis with engineered enzymes and biomimetic systems

Biocatalysis Fueled by Light: On the Versatile Combination of Photocatalysis and Enzymes

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