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Pedroso de Almeida, T. (author), van Schie, M.M.C.H. (author), Ma, A. (author), Tieves, F. (author), Younes, S.H.H. (author), Fernandez Fueyo, E. (author), Arends, I.W.C.E. (author), Riul, A. (author), Hollmann, F. (author)The selective oxidation of trans-2-hexen-1-ol to the corresponding aldehyde using a recombinant aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) is reported. Especially using the two liquid phase system to overcome solubility and product inhibition issues enabled to achieve more than 2.200.000 catalytic turnovers for the production enzyme...journal article 2019
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Zhang, W. (author), Ma, M. (author), Huijbers, M.M.E. (author), Filonenko, G.A. (author), Pidko, E.A. (author), van Schie, M.M.C.H. (author), de Boer, Sabrina (author), Smith, W.A. (author), Hollmann, F. (author)A recently discovered photodecarboxylase from Chlorella variabilis NC64A ( CvFAP) bears the promise for the efficient and selective synthesis of hydrocarbons from carboxylic acids. CvFAP, however, exhibits a clear preference for long-chain fatty acids thereby limiting its broad applicability. In this contribution, we demonstrate that the...journal article 2019
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Ma, Yunjian (author), Li, Yongru (author), Ali, Shahid (author), Li, Peilin (author), Zhang, W. (author), Rauch, M.C.R. (author), Willot, S.J. (author), Ribitsch, Doris (author), Hollmann, F. (author)Natural deep eutectic solvents (NADES) are proposed as alternative solvents for peroxygenase-catalysed oxyfunctionalization reactions. Choline chloride-based NADES are of particular interest as they can serve as solvent, enzyme-stabiliser and sacrificial electron donor for the in situ H<sub>2</sub>O<sub>2</sub> generation. This report...journal article 2019
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Younes, S.H.H. (author), Tieves, F. (author), Lan, Dongming (author), Wang, Yonghua (author), Süss, Philipp (author), Brundiek, Henrike (author), Wever, Ron (author), Hollmann, F. (author)A chemoenzymatic method for the halocyclization of unsaturated alcohols and acids by using the robust V-dependent chloroperoxidase from Curvularia inaequalis (CiVCPO) as catalyst has been developed for the in situ generation of hypohalites. A broad range of halolactones and cyclic haloethers are formed with excellent performance of the...journal article 2019
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Rauch, M.C.R. (author), Gallou, Y. (author), Delorme, L. (author), Paul, C.E. (author), Arends, I.W.C.E. (author), Hollmann, F. (author)Elemental metals are shown to be suitable sacrificial electron donors to drive the stereoselective reduction of conjugated C=C double bonds using Old Yellow Enzymes as catalysts. Both direct electron transfer from the metal to the enzyme as well as mediated electron transfer is feasible, although the latter excels by higher reaction rates....journal article 2019
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van Schie, M.M.C.H. (author), Pedroso de Almeida, T. (author), Laudadio, Gabriele (author), Tieves, F. (author), Fernandez Fueyo, E. (author), Noël, Timothy (author), Arends, I.W.C.E. (author), Hollmann, F. (author)The biocatalytic preparation of trans-hex-2-enal from trans-hex-2-enol using a novel aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) is reported. As O<sub>2</sub>-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O<sub>2</sub> in aqueous media and mass transfer limitations resulting in poor...journal article 2018
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Kim, Jinhyun (author), Lee, S.H. (author), Tieves, F. (author), Choi, Da Som (author), Hollmann, F. (author), Paul, C.E. (author), Park, Chan Beum (author)Light-driven activation of redox enzymes is an emerging route for sustainable chemical synthesis. Among redox enzymes, the family of Old Yellow Enzyme (OYE) dependent on the nicotinamide adenine dinucleotide cofactor (NADH) catalyzes the stereoselective reduction of α,β-unsaturated hydrocarbons. Here, we report OYE-catalyzed asymmetric...journal article 2018
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van Schie, M.M.C.H. (author), Younes, S.H.H. (author), Rauch, M.C.R. (author), Pesic, M. (author), Paul, C.E. (author), Arends, I.W.C.E. (author), Hollmann, F. (author)Deazaflavins are potentially useful redox mediators for the direct, nicotinamide-independent regeneration of oxidoreductases. Especially the O<sub>2</sub>-stability of their reduced forms have attracted significant interest for the regeneration of monooxygenases. In this contribution we further investigate the photochemical properties of...journal article 2018
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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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Liu, Nan (author), Liu, D. (author), Wang, Weifei (author), Hollmann, F. (author), Xu, Long (author), Ma, Yunjian (author), Yang, Bo (author), Bai, Weidong (author), Sun, Xiaotao (author), Wang, Yonghua (author)α‐Linolenic acid‐rich diacylglycerol has been demonstrated with promising health promotion functions. This study examined the production, immobilization of lipase PCL, and its application in the synthesis of diacylglycerol by esterification of α‐linolenic acid with glycerol. The resin ECR8806 was selected as an effective support for the...journal article 2018
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Dong, J. (author), Fernandez Fueyo, E. (author), Hollmann, F. (author), Paul, C.E. (author), Pesic, M. (author), Schmidt, S. (author), Wang, Yonghua (author), Younes, S.H.H. (author), Zhang, W. (author)Oxidation chemistry using enzymes is approaching maturity and practical applicability in organic synthesis. Oxidoreductases (enzymes catalysing redox reactions) enable chemists to perform highly selective and efficient transformations ranging from simple alcohol oxidations to stereoselective halogenations of non‐activated C−H bonds. For many of...journal article 2018
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Zhang, W. (author), Fernandez Fueyo, E. (author), Ni, Y. (author), van Schie, M.M.C.H. (author), Gacs, Jenö (author), Renirie, R. (author), Wever, Ron (author), Mutti, Francesco G. (author), Rother, Dörte (author), Alcalde, Miguel (author), Hollmann, F. (author)Peroxygenases offer an attractive means to address challenges in selective oxyfunctionalization chemistry. Despite this, their application in synthetic chemistry remains challenging due to their facile inactivation by the stoichiometric oxidant H<sub>2</sub>O<sub>2</sub>. Often atom-inefficient peroxide generation systems are required, which...journal article 2018
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Zhang, W. (author), Hollmann, F. (author)Oxidoreductases have become useful tools in the hands of chemists to perform selective and mild oxidation and reduction reactions. Instead of mimicking native catalytic cycles, generally involving costly and unstable nicotinamide cofactors, more direct, NAD(P)-independent methodologies are being developed. The promise of these approaches not...journal article 2018
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Huijbers, M.M.E. (author), Zhang, W. (author), Tonin, F. (author), Hollmann, F. (author)The photoenzymatic decarboxylation of fatty acids to alkanes is proposed as an alternative approach for the synthesis of biodiesel. By using a recently discovered photodecarboxylase from Chlorella variabilis NC64A (CvFAP) we demonstrate the irreversible preparation of alkanes from fatty acids and triglycerides. Several fatty acids and their...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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Huang, Lei (author), Sayoga, Giovanni Vallian (author), Hollmann, F. (author), Kara, S. (author)A direct synthesis of lactams (5-, 6-, and 7-membered) starting from amino-alcohols in a bienzymatic cascade is reported. Horse liver alcohol dehydrogenase together with the NADH oxidase from Streptococcus mutans were applied for the oxidative lactamization of various amino alcohols. Crucial parameters for the efficiency of this cascade...journal article 2018
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Hollmann, F. (author), Kara, Selin (author), Opperman, Diederik J. (author), Wang, Yonghua (author)Cyclic esters and amides (lactones and lactams) are important active ingredients and polymer building blocks. In recent years, numerous biocatalytic methods for their preparation have been developed including enzymatic and chemoenzymatic Baeyer–Villiger oxidations, oxidative lactonisation of diols, and reductive lactonisation and...journal article 2018
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Höfler, G.T. (author), Fernandez Fueyo, E. (author), Pesic, M. (author), Younes, S.H.H. (author), Choi, Eun Gyu (author), Kim, Yong H. (author), Urlacher, Vlada B. (author), Arends, I.W.C.E. (author), Hollmann, F. (author)A photoenzymatic NADH regeneration system was established. The combination of deazariboflavin as a photocatalyst with putidaredoxin reductase enabled the selective reduction of NAD<sup>+</sup> into the enzyme-active 1,4-NADH to promote an alcohol dehydrogenase catalysed stereospecific reduction reaction. The catalytic turnover of all the...journal article 2018
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Coccia, F. (author), Tonucci, Lucia (author), Del Boccio, Piero (author), Caporali, Stefano (author), Hollmann, F. (author), D’Alessandro, Nicola (author)The combination of metal nanoparticles (Pd or Pt NPs) with NAD-dependent thermostable alcohol dehydrogenase (TADH) resulted in the one-flask catalytic double reduction of 3-methyl-2-cyclohexenone to 3-(1S,3S)-methylcyclohexanol. In this article some assumptions about the interactions between a chemocatalyst and a biocatalyst have been...journal article 2018
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Combining Photo-Organo Redox- and Enzyme Catalysis Facilitates Asymmetric C-H Bond FunctionalizationZhang, W. (author), Fernandez Fueyo, E. (author), Hollmann, F. (author), Leemans Martin, L. (author), Pesic, M. (author), Wardenga, Rainer (author), Höhne, Matthias (author), Schmidt, S. (author)In this study, we combined photo-organo redox catalysis and biocatalysis to achieve asymmetric C–H bond functionalization of simple alkane starting materials. The photo-organo catalyst anthraquinone sulfate (SAS) was employed to oxyfunctionalise alkanes to aldehydes and ketones. We coupled this light-driven reaction with asymmetric enzymatic...journal article 2018