Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

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 O2-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O2 in aqueous media and mass transfer limitations resulting in poor reaction rates. These limitations were efficiently overcome by conducting the reaction in a flow-reactor setup reaching unpreceded catalytic activities for the enzyme in terms of turnover frequency (up to 38 s−1) and turnover numbers (more than 300000) pointing towards preparative usefulness of the proposed reaction scheme.

[1]  Victor Sans,et al.  Tuneable 3D printed bioreactors for transaminations under continuous-flow , 2017 .

[2]  N. Grobert,et al.  H2-Driven biocatalytic hydrogenation in continuous flow using enzyme-modified carbon nanotube columns. , 2017, Chemical communications.

[3]  Norbert Kockmann,et al.  Safety assessment in development and operation of modular continuous-flow processes , 2017 .

[4]  John M Woodley,et al.  Characterization of a continuous agitated cell reactor for oxygen dependent biocatalysis , 2017, Biotechnology and bioengineering.

[5]  P. Seeberger,et al.  The Hitchhiker's Guide to Flow Chemistry ∥. , 2017, Chemical reviews.

[6]  T. Wirth,et al.  Optimising Terpene Synthesis with Flow Biocatalysis , 2017, European journal of organic chemistry.

[7]  Ian R. Baxendale,et al.  The Use of Gases in Flow Synthesis , 2016 .

[8]  R. Luque,et al.  Liquid phase oxidation chemistry in continuous-flow microreactors. , 2016, Chemical Society reviews.

[9]  John M. Woodley,et al.  Process Requirements of Galactose Oxidase Catalyzed Oxidation of Alcohols , 2015 .

[10]  V. Hessel,et al.  Beyond organometallic flow chemistry : the principles behind the use of continuous-flow reactors for synthesis , 2015 .

[11]  S. M. Glueck,et al.  The substrate tolerance of alcohol oxidases , 2015, Applied Microbiology and Biotechnology.

[12]  David Cantillo,et al.  Continuous-flow technology—a tool for the safe manufacturing of active pharmaceutical ingredients. , 2015, Angewandte Chemie.

[13]  Frank Hollmann,et al.  Specific oxyfunctionalisations catalysed by peroxygenases: opportunities, challenges and solutions , 2015 .

[14]  A. Schmid,et al.  Regioselective Biocatalytic Aromatic Hydroxylation in a Gas–Liquid Multiphase Tube‐in‐Tube Reactor , 2014 .

[15]  Christian Hofmann,et al.  A Falling‐Film Microreactor for Enzymatic Oxidation of Glucose , 2014 .

[16]  F. Hollmann,et al.  How Green is Biocatalysis? To Calculate is To Know , 2014 .

[17]  Peter J. Miedziak,et al.  Control of the selectivity in multi-functional group molecules using supported gold–palladium nanoparticles , 2013 .

[18]  Frank Hollmann,et al.  Increasing the Productivity of Peroxidase‐Catalyzed Oxyfunctionalization: A Case Study on the Potential of Two‐Liquid‐Phase Systems , 2013 .

[19]  Michael Schlüter,et al.  Generation of Dean vortices and enhancement of oxygen transfer rates in membrane contactors for different hollow fiber geometries , 2012 .

[20]  Edward Jones,et al.  Biocatalytic oxidase: Batch to continuous , 2012 .

[21]  Ed Jones,et al.  Scaling Up Biocatalysis Reactions in Flow Reactors , 2012 .

[22]  Bernd Nidetzky,et al.  Biotransformations in microstructured reactors: more than flowing with the stream? , 2011, Trends in biotechnology.

[23]  Nicholas J Turner,et al.  Enantioselective oxidation of C-O and C-N bonds using oxidases. , 2011, Chemical reviews.

[24]  I. Arends,et al.  Enzyme-mediated oxidations for the chemist , 2011 .

[25]  J. Woodley,et al.  Guidelines and Cost Analysis for Catalyst Production in Biocatalytic Processes , 2011 .

[26]  Dietmar Haltrich,et al.  Kinetic modeling of a bi‐enzymatic system for efficient conversion of lactose to lactobionic acid , 2009, Biotechnology and bioengineering.

[27]  W. V. van Berkel,et al.  Spectral and catalytic properties of aryl-alcohol oxidase, a fungal flavoenzyme acting on polyunsaturated alcohols. , 2005, The Biochemical journal.

[28]  W. Kroutil,et al.  Recent advances in the biocatalytic reduction of ketones and oxidation of sec-alcohols. , 2004, Current opinion in chemical biology.

[29]  F. Guillén,et al.  Substrate specificity and properties of the aryl-alcohol oxidase from the ligninolytic fungus Pleurotus eryngii. , 1992, European journal of biochemistry.

[30]  Pedro Fernandes,et al.  Flow Bioreactors as Complementary Tools for Biocatalytic Process Intensification. , 2018, Trends in biotechnology.

[31]  D. Haltrich,et al.  Bubble‐free oxygenation of a bi‐enzymatic system: effect on biocatalyst stability , 2009, Biotechnology and bioengineering.

[32]  P. Ferreira,et al.  In vitro activation, purification, and characterization of Escherichia coli expressed aryl-alcohol oxidase, a unique H2O2-producing enzyme. , 2006, Protein expression and purification.

[33]  A. Karau,et al.  Deactivation of Formate Dehydrogenase (FDH) in Solution and at Gas‐Liquid Interfaces , 2005, Biotechnology progress.

[34]  Ángel T. Martínez,et al.  Production of hydrogen peroxide by aryl-alcohol oxidase from the ligninolytic fungusPleurotus eryngii , 2004, Applied Microbiology and Biotechnology.