Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases

Sandoval, Braddock A.; Clayman, Phillip D.; Oblinsky, Daniel G.; Oh, Seokjoon; Nakano, Yuji; Bird, Matthew; Scholes, Gregory D.; Hyster, Todd K.

doi:10.1021/jacs.0c11494

Title: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases

Abstract

Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor–acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within “ene”-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.

Authors:

Sandoval, Braddock A. ^[1]; Clayman, Phillip D. ^[1];

^[1];

^[2]; Nakano, Yuji ^[1];

^[2];

^[1];

^[1]

Princeton Univ., NJ (United States)
Brookhaven National Lab. (BNL), Upton, NY (United States)

Publication Date:: Thu Dec 31 00:00:00 EST 2020

Research Org.:: Princeton Univ., NJ (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1756851

Alternate Identifier(s):: OSTI ID: 1756853

Grant/Contract Number:: SC0019370

Resource Type:: Accepted Manuscript

Journal Name:: Journal of the American Chemical Society

Additional Journal Information:: Journal Volume: 143; Journal Issue: 4; Journal ID: ISSN 0002-7863

Publisher:: American Chemical Society (ACS)

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Transfer reactions; Flavins; Charge transfer; Amides; Peptides and proteins

Citation Formats


                    Sandoval, Braddock A., Clayman, Phillip D., Oblinsky, Daniel G., Oh, Seokjoon, Nakano, Yuji, Bird, Matthew, Scholes, Gregory D., and Hyster, Todd K. Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases.  United States: N. p., 2020. 
Web.  doi:10.1021/jacs.0c11494.

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                    Sandoval, Braddock A., Clayman, Phillip D., Oblinsky, Daniel G., Oh, Seokjoon, Nakano, Yuji, Bird, Matthew, Scholes, Gregory D., & Hyster, Todd K. Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases.  United States.  https://doi.org/10.1021/jacs.0c11494

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                    Sandoval, Braddock A., Clayman, Phillip D., Oblinsky, Daniel G., Oh, Seokjoon, Nakano, Yuji, Bird, Matthew, Scholes, Gregory D., and Hyster, Todd K. Thu .  
"Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases".  United States.  https://doi.org/10.1021/jacs.0c11494.  https://www.osti.gov/servlets/purl/1756851.

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@article{osti_1756851,

  title        = {Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases},

  author       = {Sandoval, Braddock A. and Clayman, Phillip D. and Oblinsky, Daniel G. and Oh, Seokjoon and Nakano, Yuji and Bird, Matthew and Scholes, Gregory D. and Hyster, Todd K.},

  abstractNote = {Non-natural photoenzymatic reactions reported to date have depended on the excitation of electron donor–acceptor complexes formed between substrates and cofactors within protein active sites to facilitate electron transfer. While this mechanism has unlocked new reactivity, it limits the types of substrates that can be involved in this area of catalysis. Here we demonstrate that direct excitation of flavin hydroquinone within “ene”-reductase active sites enables new substrates to participate in photoenzymatic reactions. We found that by using photoexcitation these enzymes gain the ability to reduce acrylamides through a single electron transfer mechanism.},

  doi          = {10.1021/jacs.0c11494},

  journal      = {Journal of the American Chemical Society},

  number       = 4,

  volume       = 143,

  place        = {United States},

  year         = {Thu Dec 31 00:00:00 EST 2020},

  month        = {Thu Dec 31 00:00:00 EST 2020}

}

Copy to clipboard

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Works referenced in this record:

Photovoltaic solar cell technologies: analysing the state of the art
journal, March 2019

Nayak, Pabitra K.; Mahesh, Suhas; Snaith, Henry J.
Nature Reviews Materials, Vol. 4, Issue 4
DOI: 10.1038/s41578-019-0097-0

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’‐Reductases with Photoredox Catalysts
journal, April 2020

Nakano, Yuji; Black, Michael J.; Meichan, Andrew J.
Angewandte Chemie International Edition, Vol. 59, Issue 26
DOI: 10.1002/anie.202003125

Old Yellow Enzyme-Catalysed Asymmetric Hydrogenation: Linking Family Roots with Improved Catalysis
journal, April 2017

Scholtissek, Anika; Tischler, Dirk; Westphal, Adrie
Catalysts, Vol. 7, Issue 12
DOI: 10.3390/catal7050130

Fluorescence and optical characteristics of reduced flavines and flavoproteins
journal, January 1974

Ghisla, Sandro; Massey, Vincent; Lhoste, Jean-Marc
Biochemistry, Vol. 13, Issue 3
DOI: 10.1021/bi00700a029

Electron hopping through proteins
journal, November 2012

Warren, Jeffrey J.; Ener, Maraia E.; Vlček, Antonín
Coordination Chemistry Reviews, Vol. 256, Issue 21-22
DOI: 10.1016/j.ccr.2012.03.032

Recent advances in photoinduced catalysis for water splitting and environmental applications
journal, April 2019

Agbe, Henry; Nyankson, Emmanuel; Raza, Nadeem
Journal of Industrial and Engineering Chemistry, Vol. 72
DOI: 10.1016/j.jiec.2019.01.004

Lewis Acid Catalyzed Enantioselective Photochemical Rearrangements on the Singlet Potential Energy Surface
journal, December 2019

Leverenz, Malte; Merten, Christian; Dreuw, Andreas
Journal of the American Chemical Society, Vol. 141, Issue 51
DOI: 10.1021/jacs.9b12068

Organic Photoredox Catalysis
journal, June 2016

Romero, Nathan A.; Nicewicz, David A.
Chemical Reviews, Vol. 116, Issue 17
DOI: 10.1021/acs.chemrev.6b00057

A Dual-Catalysis Approach to Enantioselective [2 + 2] Photocycloadditions Using Visible Light
journal, April 2014

Du, J.; Skubi, K. L.; Schultz, D. M.
Science, Vol. 344, Issue 6182
DOI: 10.1126/science.1251511

An algal photoenzyme converts fatty acids to hydrocarbons
journal, August 2017

Sorigué, Damien; Légeret, Bertrand; Cuiné, Stéphan
Science, Vol. 357, Issue 6354
DOI: 10.1126/science.aan6349

Photoenzymatic Catalysis Enables Radical‐Mediated Ketone Reduction in Ene‐Reductases
journal, June 2019

Sandoval, Braddock A.; Kurtoic, Sarah I.; Chung, Megan M.
Angewandte Chemie International Edition, Vol. 58, Issue 26
DOI: 10.1002/anie.201902005

Biocatalytic Reductions and Chemical Versatility of the Old Yellow Enzyme Family of Flavoprotein Oxidoreductases
journal, June 2010

Toogood, Helen S.; Gardiner, John M.; Scrutton, Nigel S.
ChemCatChem, Vol. 2, Issue 8
DOI: 10.1002/cctc.201000094

Photoexcitation of flavoenzymes enables a stereoselective radical cyclization
journal, June 2019

Biegasiewicz, Kyle F.; Cooper, Simon J.; Gao, Xin
Science, Vol. 364, Issue 6446
DOI: 10.1126/science.aaw1143

Enantioselective Lewis Acid Catalysis of Intramolecular Enone [2+2] Photocycloaddition Reactions
journal, November 2013

Brimioulle, R.; Bach, T.
Science, Vol. 342, Issue 6160
DOI: 10.1126/science.1244809

The Organic-Synthetic Potential of Recombinant Ene Reductases: Substrate-Scope Evaluation and Process Optimization
journal, March 2015

Reß, Tina; Hummel, Werner; Hanlon, Steven P.
ChemCatChem, Vol. 7, Issue 8
DOI: 10.1002/cctc.201402903

Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent ‘Ene’-Reductases
journal, August 2017

Sandoval, Braddock A.; Meichan, Andrew J.; Hyster, Todd K.
Journal of the American Chemical Society, Vol. 139, Issue 33
DOI: 10.1021/jacs.7b05468

Quantification and Theoretical Analysis of the Electrophilicities of Michael Acceptors
journal, September 2017

Allgäuer, Dominik S.; Jangra, Harish; Asahara, Haruyasu
Journal of the American Chemical Society, Vol. 139, Issue 38
DOI: 10.1021/jacs.7b05106

Photoenzymatic Generation of Unstabilized Alkyl Radicals: An Asymmetric Reductive Cyclization
journal, August 2020

Clayman, Phillip D.; Hyster, Todd K.
Journal of the American Chemical Society, Vol. 142, Issue 37
DOI: 10.1021/jacs.0c07918

Synthetic Methods Driven by the Photoactivity of Electron Donor–Acceptor Complexes
journal, March 2020

Crisenza, Giacomo E. M.; Mazzarella, Daniele; Melchiorre, Paolo
Journal of the American Chemical Society, Vol. 142, Issue 12
DOI: 10.1021/jacs.0c01416

Selective C–F Functionalization of Unactivated Trifluoromethylarenes
journal, August 2019

Vogt, David B.; Seath, Ciaran P.; Wang, Hengbin
Journal of the American Chemical Society, Vol. 141, Issue 33
DOI: 10.1021/jacs.9b06004

Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis
journal, July 2019

Zheng, Jian; Swords, Wesley B.; Jung, Hoimin
Journal of the American Chemical Society, Vol. 141, Issue 34
DOI: 10.1021/jacs.9b06244

Potentiometric studies of native and flavin-substituted Old Yellow Enzyme.
journal, November 1985

Stewart, R. C.; Massey, V.
Journal of Biological Chemistry, Vol. 260, Issue 25
DOI: 10.1016/S0021-9258(17)38773-2

Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans
journal, August 2010

Richter, Nina; Gröger, Harald; Hummel, Werner
Applied Microbiology and Biotechnology, Vol. 89, Issue 1
DOI: 10.1007/s00253-010-2793-y

Enantioselective photochemistry through Lewis acid–catalyzed triplet energy transfer
journal, December 2016

Blum, Travis R.; Miller, Zachary D.; Bates, Desiree M.
Science, Vol. 354, Issue 6318
DOI: 10.1126/science.aai8228

Dynamics and mechanisms of DNA repair by photolyase
journal, January 2015

Liu, Zheyun; Wang, Lijuan; Zhong, Dongping
Physical Chemistry Chemical Physics, Vol. 17, Issue 18
DOI: 10.1039/C4CP05286B

Applications of protein engineering to members of the old yellow enzyme family
journal, September 2015

Amato, Erica D.; Stewart, Jon D.
Biotechnology Advances, Vol. 33, Issue 5
DOI: 10.1016/j.biotechadv.2015.04.011

The Oxidative Half-reaction of Old Yellow Enzyme
journal, December 1998

Kohli, Rahul M.; Massey, Vincent
Journal of Biological Chemistry, Vol. 273, Issue 49
DOI: 10.1074/jbc.273.49.32763

Kinetics and Pathways of Charge Recombination in Photosystem II ^†
journal, July 2002

Rappaport, Fabrice; Guergova-Kuras, Mariana; Nixon, Peter J.
Biochemistry, Vol. 41, Issue 26
DOI: 10.1021/bi025725p

The molecular origin of high DNA-repair efficiency by photolyase
journal, June 2015

Tan, Chuang; Liu, Zheyun; Li, Jiang
Nature Communications, Vol. 6, Issue 1
DOI: 10.1038/ncomms8302

Catalytic Defluoroalkylation of Trifluoromethylaromatics with Unactivated Alkenes
journal, December 2017

Wang, Hengbin; Jui, Nathan T.
Journal of the American Chemical Society, Vol. 140, Issue 1
DOI: 10.1021/jacs.7b12590

Photoenzymes and Related Topics: An Update
journal, March 2018

Björn, Lars Olof
Photochemistry and Photobiology, Vol. 94, Issue 3
DOI: 10.1111/php.12892

Accessing non-natural reactivity by irradiating nicotinamide-dependent enzymes with light
journal, December 2016

Emmanuel, Megan A.; Greenberg, Norman R.; Oblinsky, Daniel G.
Nature, Vol. 540, Issue 7633
DOI: 10.1038/nature20569

Water oxidation in photosystem II
journal, June 2019

Lubitz, Wolfgang; Chrysina, Maria; Cox, Nicholas
Photosynthesis Research, Vol. 142, Issue 1
DOI: 10.1007/s11120-019-00648-3

Redox-photosensitized reactions. 11. Ru(bpy)32+-photosensitized reactions of 1-benzyl-1,4-dihydronicotinamide with aryl-substituted enones, derivatives of methyl cinnamate, and substituted cinnamonitriles: electron-transfer mechanism and structure-reactivity relationships
journal, January 1984

Pac, Chyongjin; Miyauchi, Yoji; Ishitani, Osamu
The Journal of Organic Chemistry, Vol. 49, Issue 1
DOI: 10.1021/jo00175a006

Emerging strategies for expanding the toolbox of enzymes in biocatalysis
journal, April 2020

Sandoval, Braddock A.; Hyster, Todd K.
Current Opinion in Chemical Biology, Vol. 55
DOI: 10.1016/j.cbpa.2019.12.006

Selective Single C(sp ³ )–F Bond Cleavage in Trifluoromethylarenes: Merging Visible-Light Catalysis with Lewis Acid Activation
journal, December 2017

Chen, Kang; Berg, Nele; Gschwind, Ruth
Journal of the American Chemical Society, Vol. 139, Issue 51
DOI: 10.1021/jacs.7b10755

Asymmetric bioreduction of activated alkenes to industrially relevant optically active compounds
journal, December 2012

Winkler, Christoph K.; Tasnádi, Gábor; Clay, Dorina
Journal of Biotechnology, Vol. 162, Issue 4
DOI: 10.1016/j.jbiotec.2012.03.023

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Title: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent “Ene”-Reductases

Abstract

Citation Formats

Photovoltaic solar cell technologies: analysing the state of the art journal, March 2019

Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’‐Reductases with Photoredox Catalysts journal, April 2020

Old Yellow Enzyme-Catalysed Asymmetric Hydrogenation: Linking Family Roots with Improved Catalysis journal, April 2017

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Recent advances in photoinduced catalysis for water splitting and environmental applications journal, April 2019

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Organic Photoredox Catalysis journal, June 2016

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An algal photoenzyme converts fatty acids to hydrocarbons journal, August 2017

Photoenzymatic Catalysis Enables Radical‐Mediated Ketone Reduction in Ene‐Reductases journal, June 2019

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Enantioselective Lewis Acid Catalysis of Intramolecular Enone [2+2] Photocycloaddition Reactions journal, November 2013

The Organic-Synthetic Potential of Recombinant Ene Reductases: Substrate-Scope Evaluation and Process Optimization journal, March 2015

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Applications of protein engineering to members of the old yellow enzyme family journal, September 2015

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Emerging strategies for expanding the toolbox of enzymes in biocatalysis journal, April 2020

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journal, March 2019

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journal, April 2017

Fluorescence and optical characteristics of reduced flavines and flavoproteins
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journal, November 2012

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journal, April 2019

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journal, December 2019

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journal, April 2014

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journal, August 2017

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The Organic-Synthetic Potential of Recombinant Ene Reductases: Substrate-Scope Evaluation and Process Optimization
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journal, September 2017

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journal, August 2020

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journal, March 2020

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journal, August 2019

Enantioselective Intermolecular Excited-State Photoreactions Using a Chiral Ir Triplet Sensitizer: Separating Association from Energy Transfer in Asymmetric Photocatalysis
journal, July 2019

Potentiometric studies of native and flavin-substituted Old Yellow Enzyme.
journal, November 1985

Asymmetric reduction of activated alkenes using an enoate reductase from Gluconobacter oxydans
journal, August 2010

Enantioselective photochemistry through Lewis acid–catalyzed triplet energy transfer
journal, December 2016

Dynamics and mechanisms of DNA repair by photolyase
journal, January 2015

Applications of protein engineering to members of the old yellow enzyme family
journal, September 2015

The Oxidative Half-reaction of Old Yellow Enzyme
journal, December 1998

Kinetics and Pathways of Charge Recombination in Photosystem II ^†
journal, July 2002

The molecular origin of high DNA-repair efficiency by photolyase
journal, June 2015

Catalytic Defluoroalkylation of Trifluoromethylaromatics with Unactivated Alkenes
journal, December 2017

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journal, March 2018

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journal, December 2016

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journal, June 2019

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journal, January 1984

Emerging strategies for expanding the toolbox of enzymes in biocatalysis
journal, April 2020

Selective Single C(sp ³ )–F Bond Cleavage in Trifluoromethylarenes: Merging Visible-Light Catalysis with Lewis Acid Activation
journal, December 2017

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journal, December 2012