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Zhang, W. (author), Li, Huanhuan (author), Younes, S.H.H. (author), Gómez De Santos, Patricia (author), Tieves, F. (author), Grogan, Gideon (author), Pabst, Martin (author), Alcalde, Miguel (author), Whitwood, Adrian C. (author), Hollmann, F. (author)
Aromatic hydroxylation reactions catalyzed by heme-thiolate enzymes proceed via an epoxide intermediate. These aromatic epoxides could be valuable building blocks for organic synthesis giving access to a range of chiral trans-disubstituted cyclohexadiene synthons. Here, we show that naphthalene epoxides generated by fungal peroxygenases can...
journal article 2021
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Tonin, F. (author), Tieves, F. (author), Willot, S.J. (author), Van Troost, Anouska (author), van Oosten, R.J.C. (author), Breestraat, Stefaan (author), Van Pelt, Sander (author), Alcalde, Miguel (author), Hollmann, F. (author)
The pilot-scale production of the peroxygenase from Agrocybe aegerita (rAaeUPO) is demonstrated. In a fed-batch fermentation of the recombinant Pichia pastoris, the enzyme was secreted into the culture medium to a final concentration of 0.29 g L-1 corresponding to 735 g of the peroxygenase in 2500 L of the fermentation broth after 6 days. Due...
journal article 2021
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van Schie, M.M.C.H. (author), Kaczmarek, Alexander T. (author), Tieves, F. (author), Gomez de Santos, Patricia (author), Paul, C.E. (author), Arends, I.W.C.E. (author), Alcalde, Miguel (author), Schwarz, Günter (author), Hollmann, F. (author)
H<sub>2</sub>O<sub>2</sub> can be accepted by several peroxygenases as a clean oxidant, able to supply both the necessary electrons and oxygen atom at the same time. The biocatalysts, in turn, are able to catalyse an array of interesting oxygen insertion reactions at enantio- and regio-selectivities hard to attain with classical chemical...
journal article 2020
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Yoon, Jaeho (author), Kim, Jinhyun (author), Tieves, F. (author), Zhang, W. (author), Alcalde, Miguel (author), Hollmann, F. (author), Park, Chan Beum (author)
Peroxygenases have long inspired the selective oxyfunctionalization of various aliphatic and aromatic compounds, because of their broad substrate spectrum and simplicity of catalytic mechanism. This study provides a proof-of-concept of piezobiocatalysis by demonstrating peroxygenase-catalyzed oxyfunctionalization reactions fueled by...
journal article 2020
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Gomez de Santos, P. (author), Cervantes, Fadia V. (author), Tieves, F. (author), Plou, Francisco J. (author), Hollmann, F. (author), Alcalde, Miguel (author)
By mimicking the role of human liver P450 monooxygenases, fungal unspecific peroxygenases (UPOs) can perform a range of highly selective oxyfunctionalization reactions on pharmacological compounds, including O-dealkylations and hydroxylations, thereby simulating drug metabolism. Here we have benchmarked human drug metabolite (HDM) synthesis...
journal article 2019
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Burek, Bastien O. (author), de Boer, Sabrina R. (author), Tieves, F. (author), Zhang, W. (author), van Schie, M.M.C.H. (author), Bormann, Sebastian (author), Alcalde, Miguel (author), Holtmann, Dirk (author), Hollmann, F. (author)
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<sub>2</sub>O<sub>2</sub> generation. Here, we report the “on demand” production of hydrogen peroxide via methanol assisted reduction of molecular oxygen using UV...
journal article 2019
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van Schie, M.M.C.H. (author), Zhang, W. (author), Tieves, F. (author), Choi, Da Som (author), Park, Chan Beum (author), Burek, Bastien O. (author), Bloh, Jonathan Z. (author), Arends, I.W.C.E. (author), Paul, C.E. (author), Alcalde, Miguel (author), Hollmann, F. (author)
Peroxygenases are very interesting catalysts for specific oxyfunctionalization chemistry. Instead of relying on complicated electron transport chains, they rely on simple hydrogen peroxide as the stoichiometric oxidant. Their poor robustness against H<sub>2</sub>O<sub>2</sub> can be addressed via in situ generation of H<sub>2</sub>O<sub>2<...
journal article 2019
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Rauch, M.C.R. (author), Tieves, F. (author), Paul, C.E. (author), Arends, I.W.C.E. (author), Alcalde, Miguel (author), Hollmann, F. (author)
Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.
journal article 2019
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Tieves, F. (author), Tonin, F. (author), Fernandez Fueyo, E. (author), Robbins, John M. (author), Bommarius, Bettina (author), Bommarius, Andreas S. (author), Alcalde, Miguel (author), Hollmann, F. (author)
The E-factor has become an important measure for the environmental impact of (bio)chemical reactions. However, summing up the obvious wastes generated in the laboratory neglects energy-related wastes (mostly greenhouse gases) which are generated elsewhere. To estimate these wastes, we propose to extend the E-factor by an energy-term (E<sup>+<...
journal article 2019
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Willot, S.J. (author), Fernandez Fueyo, E. (author), Tieves, F. (author), Pesic, M. (author), Alcalde, Miguel (author), Arends, I.W.C.E. (author), Park, Chan Beum (author), Hollmann, F. (author)
Peroxygenases require a controlled supply of H<sub>2</sub>O<sub>2</sub> to operate efficiently. Here, we propose a photocatalytic system for the reductive activation of ambient O<sub>2</sub> to produce H<sub>2</sub>O<sub>2</sub> which uses the energy provided by visible light more efficiently based on the combination of wavelength...
journal article 2019
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Gomez De Santos, Patricia (author), Cañellas, Marina (author), Tieves, F. (author), Younes, S.H.H. (author), Molina-Espeja, Patricia (author), Hofrichter, Martin (author), Hollmann, F. (author), Guallar, Victor (author), Alcalde, Miguel (author)
Propranolol is a widely used beta-blocker that is metabolized by human liver P450 monooxygenases into equipotent hydroxylated human drug metabolites (HDMs). It is paramount for the pharmaceutical industry to evaluate the toxicity and activity of these metabolites, but unfortunately, their synthesis has hitherto involved the use of severe...
journal article 2018
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Pesic, M. (author), Willot, S.J. (author), Fernandez Fueyo, E. (author), Tieves, F. (author), Alcalde, Miguel (author), Hollmann, F. (author)
There is an increasing interest in the application of peroxygenases in biocatalysis, because of their ability to catalyse the oxyfunctionalisation reaction in a stereoselective fashion and with high catalytic efficiencies, while using hydrogen peroxide or organic peroxides as oxidant. However, enzymes belonging to this class exhibit a very...
journal article 2018
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