Abstract
Oxidoreductases are enzymes with a high potential for organic synthesis, as their selectivity often exceeds comparable chemical syntheses. The biochemical cofactors of these enzymes need regeneration during synthesis. Several regeneration methods are available but the electrochemical approach offers an efficient and quasi mass-free method for providing the required redox equivalents. Electron transfer systems involving direct regeneration of natural and artificial cofactors, indirect electrochemical regeneration via a mediator, and indirect electroenzymatic cofactor regeneration via enzyme and mediator have been investigated. This chapter gives an overview of electroenzymatic syntheses with oxidoreductases, structured by the enzyme subclass and their usage of cofactors for electron relay. Particular attention is given to the productivity of electroenzymatic biotransformation processes. Because most electroenzymatic syntheses suffer from low productivity, we discuss reaction engineering concepts to overcome the main limiting factors, with a focus on media conductivity optimization, approaches to prevent enzyme inactivation, and the application of advanced cell designs.
References
Das P, Das M, Chinnadayyala SR, Singha IM, Goswami P (2016) Recent advances on developing 3rd generation enzyme electrode for biosensor applications. Biosens Bioelectron 79:386–397
Yu EH, Scott K (2010) Enzymatic biofuel cells-fabrication of enzyme electrodes. Energies 3(1):23–42
Pankratov D, Conzuelo F, Pinyou P, Alsaoub S, Schuhmann W, Shleev S (2016) A nernstian biosupercapacitor. Angew Chem 55(49):15434–15438
Sode K, Yamazaki T, Lee I, Hanashi T, Tsugawa W (2016) BioCapacitor: a novel principle for biosensors. Biosens Bioelectron 76:20–28
Steckhan E (1994) Electroenzymatic synthesis. Top Curr Chem 170:83–111
Steckhan E, Arns T, Heineman WR, Hilt G, Hoormann D, Jorissen J, Kroner L, Lewall B, Putter H (2001) Environmental protection and economization of resources by electroorganic and electroenzymatic syntheses. Chemosphere 43(1):63–73
Kohlmann C, Lütz S (2015) Electroenzymatic synthesis. In: Hammerich O (ed) Organic electrochemistry5th edn. CRC Press, New York, pp 1511–1542
Paul CE, Hollmann F (2016) A survey of synthetic nicotinamide cofactors in enzymatic processes. Appl Microbiol Biotechnol 100(11):4773–4778
Wandrey C, Liese A, Kihumbu D (2000) Industrial biocatalysis: past, present, and future. Org Process Res Dev 4(4):286–290
Hummel W, Kula MR (1989) Dehydrogenases for the synthesis of chiral compounds. Eur J Biochem 184(1):1–13
Wichmann R, Wandrey C, Buckmann AF, Kula MR (1981) Continuous enzymatic transformation in an enzyme membrane reactor with simultaneous NAD(H) regeneration. Biotechnol Bioeng 23(12):2789–2802
van der Donk WA, Zhao HM (2003) Recent developments in pyridine nucleotide regeneration. Curr Opin Biotechnol 14(4):421–426
Hollmann F, Schmid A (2004) Electrochemical regeneration of oxidoreductases for cell-free biocatalytic redox reactions. Biocatal Biotransform 22(2):63–88
Uppada V, Bhaduri S, Noronha SB (2014) Cofactor regeneration – an important aspect of biocatalysis. Curr Sci 106(7):946–957
Tishkov VI, Popov VO (2004) Catalytic mechanism and application of formate dehydrogenase. Biochem Mosc 69(11):1252–1267
Chenault HK, Simon ES, Whitesides GM (1988) Cofactor regeneration for enzyme-catalysed synthesis. Biotechnol Genet Eng Rev 6(1):221–270
Nagesetti A, Rodzinski A, Stimphil E, Khanal TSC, Wang P, Guduru R, Liang P, Agoulnik I, Horstmyer J, Khizroev S (2017) Multiferroic coreshell magnetoelectric nanoparticles as NMR sensitive nanoprobes for cancer cell detection. Sci Rep 7(1):1610
Ruinatscha R, Höllrigl V, Otto K, Schmid A (2006) Productivity of selective electroenzymatic reduction and oxidation reactions: theoretical and practical considerations. Adv Synth Catal 348(15):2015–2026
Wandrey C (2004) Biochemical reaction engineering for redox reactions. Chem Rec 4(4):254–265
Grieshaber D, MacKenzie R, Voros J, Reimhult E (2008) Electrochemical biosensors – sensor principles and architectures. Sensors 8(3):1400–1458
Steckhan E (1986) Indirect electroorganic syntheses – a modern chapter of organic electrochemistry. Angew Chem 25(8):683–701
Goldberg K, Schroer K, Lütz S, Liese A (2007) Biocatalytic ketone reduction – a powerful tool for the production of chiral alcohols, part I: processes with isolated enzymes. Appl Microbiol Biotechnol 76(2):237–248
Bonnefoy J, Moiroux J, Laval JM, Bourdillon C (1988) Electrochemical regeneration of NAD+ – a new evaluation of its actual yield. J Chem Soc Faraday Trans 84:941–950
Manjon A, Obon JM, Casanova P, Fernandez VM, Ilborra JL (2002) Increased activity of glucose dehydrogenase co-immobilized with a redox mediator in a bioreactor with electrochemical NAD+ regeneration. Biotechnol Lett 24(15):1227–1232
Obon JM, Casanova P, Manjon A, Fernandez VM, Iborra JL (1997) Stabilization of glucose dehydrogenase with polyethyleneimine in an electrochemical reactor with NAD(P)+ regeneration. Biotechnol Prog 13(5):557–561
Hilt G, Steckhan E (1993) Transition-metal complexes of 1,10-phenanthroline-5,6-dione as efficient mediators for the regeneration of NAD+ in enzymatic-synthesis. J Chem Soc Chem Commun 22:1706–1707
Hilt G, Lewall B, Montero G, Utley JHP, Steckhan E (1997) Efficient in situ redox catalytic NAD(P)+ regeneration in enzymatic synthesis using transition-metal complexes of 1,10-phenanthroline-5,6-dione and its N-monomethylated derivative as catalysts. Liebigs Ann Recl 11:2289–2296
Komoschinski J, Steckhan E (1988) Efficient indirect electrochemical in situ regeneration of NAD+ and NADP+ for enzymatic oxidations using iron bipyridine and phenanthroline complexes as redox catalysts. Tetrahedron Lett 29(27):3299–3300
Itoh S, Fukushima H, Komatsu M, Ohshiro Y (1992) Heterocyclic ortho-quinones – mediator for electrochemical oxidation of NADH. Chem Lett 8:1583–1586
Kashiwagi Y, Osa T (1993) Electrocatalytic oxidation of NADH on thin poly(acrylic acid) film coated graphite felt electrode coimmobilizing ferrocene and diaphorase. Chem Lett 4:677–680
Schulz M, Leichmann H, Gunther H, Simon H (1995) Electromicrobial regeneration of pyridine-nucleotides and other preparative redox transformations with Clostridium thermoaceticum. Appl Microbiol Biotechnol 42(6):916–922
Schroeder I, Steckhan E, Liese A (2003) In situ NAD+ regeneration using 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) as an electron transfer mediator. J Electroanal Chem 541:109–115
Kochius S, Park JB, Ley C, Konst P, Hollmann F, Schrader J, Holtmann D (2014) Electrochemical regeneration of oxidised nicotinamide cofactors in a scalable reactor. J Mol Catal B Enzym 103:94–99
Degenring D, Schroder I, Wandrey C, Liese A, Greiner L (2004) Resolution of 1,2-diols by enzyme-catalyzed oxidation with anodic, mediated cofactor regeneration in the extractive membrane reactor: gaining insight by adaptive simulation. Org Process Res Dev 8(2):213–218
Wulf H, Perzborn M, Sievers G, Scholz F, Bornscheuer UT (2012) Kinetic resolution of glyceraldehyde using an aldehyde dehydrogenase from Deinococcus geothermalis DSM 11300 combined with electrochemical cofactor recycling. J Mol Catal B Enzym 74(1-2):144–150
Baik SH, Kang C, Jeon IC, Yun SE (1999) Direct electrochemical regeneration of NADH from NAD+ using cholesterol-modified gold amalgam electrode. Biotechnol Tech 13(1):1–5
Siu E, Won K, Park CB (2007) Electrochemical regeneration of NADH using conductive vanadia-silica xerogels. Biotechnol Prog 23(1):293–296
Kashiwagi Y, Yanagisawa Y, Shibayama N, Nakahara K, Kurashima F, Anzai J, Osa T (1997) Preparative, electroenzymatic reduction of ketones on an all components-immobilized graphite felt electrode. Electrochim Acta 42(13–14):2267–2270
Kang YW, Kang C, Hong JS, Yun SE (2001) Optimization of the mediated electrocatalytic reduction of NAD+ by cyclic voltammetry and construction of electrochemically driven enzyme bioreactor. Biotechnol Lett 23(8):599–604
Kim MH, Yun SE (2004) Construction of an electro-enzymatic bioreactor for the production of (R)-mandelate from benzoylformate. Biotechnol Lett 26(1):21–26
Delecouls-Servat K, Basseguy R, Bergel A (2002) Designing membrane electrochemical reactors for oxidoreductase-catalysed synthesis. Bioelectrochemistry 55(1–2):93–95
DiCosimo R, Wong CH, Daniels L, Whitesides GM (1981) Enzyme-catalyzed organic-synthesis – electrochemical regeneration of NAD(P)H from NAD(P) using methyl viologen and flavoenzymes. J Org Chem 46(22):4622–4623
Cantet J, Bergel A, Comtat M (1996) Coupling of the electroenzymatic reduction of NAD+ with a synthesis reaction. Enzyme Microb Technol 18(1):72–79
Cantet J, Bergel A, Comtat M (1992) Bioelectrocatalysis of NAD+ reduction. Bioelectrochem Bioenergy 27(3):475–486
Yuan R, Watanabe S, Kuwabata S, Yoneyama H (1997) Asymmetric electroreduction of ketone and aldehyde derivatives to the corresponding alcohols using alcohol dehydrogenase as an electrocatalyst. J Org Chem 62(8):2494–2499
Hollmann F, Lin PC, Witholt B, Schmid A (2003) Stereospecific biocatalytic epoxidation: the first example of direct regeneration of a FAD-dependent monooxygenase for catalysis. J Am Chem Soc 125(27):8209–8217
Wienkamp R, Steckhan E (1982) Indirect electrochemical regeneration of NADH by a bipyridinerhodium(I) complex as electron-transfer agent. Angew Chem 21(10):782–783
Ruppert R, Herrmann S, Steckhan E (1987) Efficient indirect electrochemical in situ regeneration of NADH – electrochemically driven enzymatic reduction of pyruvate catalyzed by D-LDH. Tetrahedron Lett 28(52):6583–6586
Delecouls-Servat K, Basseguy R, Bergel A (2002) Membrane electrochemical reactor (MER): application to NADH regeneration for ADH-catalysed synthesis. Chem Eng Sci 57(21):4633–4642
Hildebrand F, Lütz S (2007) Electroenzymatic synthesis of chiral alcohols in an aqueous-organic two-phase system. Tetrahedron-Asymmetry 18(10):1187–1193
Hoellrigl V, Otto K, Schmid A (2007) Electroenzymatic asymmetric reduction of rac-3-methylcyclohexanone to (1S,3S)-3-methylcyclohexanol in organic/aqueous media catalyzed by a thermophilic alcohol dehydrogenase. Adv Synth Catal 349(8-9):1337–1340
Hildebrand F, Lütz S (2009) Stable electroenzymatic processes by catalyst separation. Chem Eur J 15(20):4998–5001
Toogood HS, Knaus T, Scrutton NS (2014) Alternative hydride sources for ene-reductases: current trends. ChemCatChem 6(4):951–954
Simon H, Gunther H, Bader J, Tischer W (1981) Electro-enzymatic and electro-microbial stereospecific reductions. Angew Chem 20(10):861–863
Thanos ICG, Simon H (1987) Electro-enzymatic viologen-mediated stereospecific reduction of 2-enoates with free and immobilized enoate reductase on cellulose filters or modified carbon electrodes. J Biotechnol 6(1):13–29
Fisher K, Mohr S, Mansell D, Goddard NJ, Fielden PR, Scrutton NS (2013) Electro-enzymatic viologen-mediated substrate reduction using pentaerythritol tetranitrate reductase and a parallel, segmented fluid flow system. Catal Sci Technol 3(6):1505–1511
Tosstorff A, Kroner C, Opperman DJ, Hollmann F, Holtmann D (2017) Towards electroenzymatic processes involving old yellow enzymes and mediated cofactor regeneration. Eng Life Sci 1:71–76
Trost E-M, Fischer L (2002) Minimization of by-product formation during amino acid oxidase catalyzed racemate resolution of amino acids. J Mol Catal B Enzym 19-20:189–195
Butó S, Pollegioni L, D’Angiuro L, Pilone MS (1994) Evaluation of D-amino-acid oxidase from Rhodotorula gracilis for the production of α-keto acids: a reactor system. Biotechnol Bioeng 44:1288–1294
Frede M, Steckhan E (1991) Continuous electrochemical activation of flavoenzymes using polyethyleneglycol-bound ferrocenes as mediators – a model for the application of oxidoreductases as oxidation catalysts in organic synthesis. Tetrahedron Lett 32(38):5063–5066
Cass AE, Davis G, Francis GD, Hill HA, Aston WJ, Higgins IJ, Plotkin EV, Scott LD, Turner AP (1984) Ferrocene-mediated enzyme electrode for amperometric determination of glucose. Anal Chem 56(4):667–671
Hill HAO, Oliver BN, Page DJ, Hopper DJ (1985) The enzyme-catalyzed electrochemical conversion of para-cresol into para-hydroxybenzaldehyde. J Chem Soc Chem Commun 21:1469–1471
Brielbeck B, Frede M, Steckhan E (1994) Continuous electroenzymatic synthesis employing the electrochemical enzyme membrane reactor. Biocatalysis 10(1-4):49–64
Petersen A, Steckhan E (1999) Continuous indirect electrochemical regeneration of galactose oxidase. Bioorg Med Chem 7(10):2203–2208
Kohlmann C, Greiner L, Leitner W, Wandrey C, Lütz S (2009) Ionic liquids as performance additives for electroenzymatic syntheses. Chem Eur J 15(43):11692–11700
Kawabata S, Iwata N, Yoneyama H (2000) Asymmetric electrosynthesis of amino acid using an electrode modified with amino acid oxidase and electron mediator. Chem Lett 2:110–111
Jeon JS, Shin IH, Sang BI, Park DH (2005) Electrochemical regeneration of FAD by catalytic electrode without electron mediator and biochemical reducing power. J Microbiol Biotechnol 15(2):281–286
Sono M, Roach MP, Coulter ED, Dawson JH (1996) Heme-containing oxygenases. Chem Rev 96(7):2841–2888
Cirino PC, Arnold FH (2002) Protein engineering of oxygenases for biocatalysis. Curr Opin Chem Biol 6(2):130–135
Faber K (2000) Biotransformations in organic chemistry, 4th edn. Springer, New York (5th edn available)
Creveling CR, Daly JW, Witkop B, Undenfriend S (1962) Substrates and inhibitors of dopamine-beta-oxidase. Biochim Biophys Acta 64:125–134
Girhard M, Bakkes PJ, Mahmoud O, Urlacher VB (2005) P450 biotechnology. In: de Montellano O (ed) Cytochrome P450: structure, mechanism, and biochemistry, 3rd edn. Kluwer Academic/Plenum, New York, pp 451–520
Kaufman S (1963) The structure of the phenylalanine-hydroxylation cofactor. PNAS 50:1085–1093
Suske WA, Held M, Schmid A, Fleischmann T, Wubbolts MG, Kohler HPE (1997) Purification and characterization of 2-hydroxybiphenyl 3-monooxygenase, a novel NADH-dependent, FAD-containing aromatic hydroxylase from Pseudomonas azelaica HBP1. J Biol Chem 272(39):24257–24265
Faulkner KM, Shet MS, Fisher CW, Estabrook RW (1995) Electrocatalytically driven omega-hydroxylation of fatty-acids using cytochrome-P450 4A1. PNAS 92(17):7705–7709
Estabrook RW, Faulkner KM, Shet MS, Fisher CW (1996) Application of electrochemistry for P450-catalyzed reactions. Methods Enzymol 272:44–51
Udit AK, Arnold FH, Gray HB (2004) Cobaltocene-mediated catalytic monooxygenation using holo and heme domain cytochrome P450BM3. J Inorg Biochem 98(9):1547–1550
Çekiç SZ, Holtmann D, Güven G, Mangold K-M, Schwaneberg U, Schrader J (2010) Mediated electron transfer with P450cin. Electrochem Commun 12(11):1547–1550
Hollmann F, Schmid A, Steckhan E (2001) The first synthetic application of a monooxygenase employing indirect electrochemical NADH regeneration. Angew Chem Int Ed 40(1):169–171
Hollmann F, Hofstetter K, Habicher T, Hauer B, Schmid A (2005) Direct electrochemical regeneration of monooxygenase subunits for biocatalytic asymmetric epoxidation. J Am Chem Soc 127(18):6540–6541
Ruinatscha R, Buehler K, Schmid A (2014) Development of a high performance electrochemical cofactor regeneration module and its application to the continuous reduction of FAD. J Mol Catal B Enzym 103:100–105
Tosstorff A, Dennig A, Ruff AJ, Schwaneberg U, Sieber V, Mangold K-M, Schrader J, Holtmann D (2014) Mediated electron transfer with monooxygenases—insight in interactions between reduced mediators and the co-substrate oxygen. J Mol Catal B Enzym 108:51–58
Ströhle FW, Cekic SZ, Magnusson AO, Schwaneberg U, Roccatano D, Schrader J, Holtmann D (2013) A computational protocol to predict suitable redox mediators for substitution of NAD(P)H in P450 monooxygenases. J Mol Catal B Enzym 88:47–51
Ley C, Schewe H, Ströhle FW, Ruff AJ, Schwaneberg U, Schrader J, Holtmann D (2013) Coupling of electrochemical and optical measurements in a microtiter plate for the fast development of electro enzymatic processes with P450s. J Mol Catal B Enzym 92:71–78
Seelbach K, van Deurzen MPJ, van Rantwijk F, Sheldon RA, Kragl U (1997) Improvement of the total turnover number and space-time yield for chloroperoxidase catalyzed oxidation. Biotechnol Bioeng 55(2):283–288
van de Velde F, van Rantwijk F, Sheldon RA (1999) Selective oxidations with molecular oxygen, catalyzed by chloroperoxidase in the presence of a reductant. J Mol Catal B Enzym 6(5):453–461
Pletcher D (1999) Indirect oxidations using electrogenerated hydrogen peroxide. Acta Chem Scand 53(10):745–750
Chen JK, Nobe K (1993) Oxidation of dimethylaniline by horseradish-peroxidase and electrogenerated peroxide. J Electrochem Soc 140(2):299–303
Lee K, Moon SH (2003) Electroenzymatic oxidation of veratryl alcohol by lignin peroxidase. J Biotechnol 102(3):261–268
Laane C, Weyland A, Franssen M (1986) Bioelectrosynthesis of halogenated compounds using chloroperoxidase. Enzyme Microb Technol 8(6):345–348
Dembitsky VM (2003) Oxidation, epoxidation and sulfoxidation reactions catalysed by haloperoxidases. Tetrahedron 59(26):4701–4720
Lütz S, Steckhan E, Liese A (2004) First asymmetric electroenzymatic oxidation catalyzed by a peroxidase. Electrochem Commun 6(6):583–587
Lütz S, Vuorilehto K, Liese A (2007) Process development for the electroenzymatic synthesis of (R)-methylphenylsulfoxide by use of a 3-dimensional electrode. Biotechnol Bioeng 98:525–534
Kohlmann C, Lütz S (2006) Electroenzymatic synthesis of chiral sulfoxides. Eng Life Sci 6(2):170–174
Krieg T, Huttmann S, Mangold KM, Schrader J, Holtmann D (2011) Gas diffusion electrode as novel reaction system for an electro-enzymatic process with chloroperoxidase. Green Chem 13(10):2686–2689
Holtmann D, Krieg T, Getrey L, Schrader J (2014) Electroenzymatic process to overcome enzyme instabilities. Catal Commun 51:82–85
Horst AEW, Bormann S, Meyer J, Steinhagen M, Ludwig R, Drews A, Ansorge-Schumacher M, Holtmann D (2016) Electro-enzymatic hydroxylation of ethylbenzene by the evolved unspecific peroxygenase of Agrocybe aegerita. J Mol Catal B Enzym. https://doi.org/10.1016/j.molcatb.2016.12.008
Slusarczyk H, Felber S, Kula MR, Pohl M (2000) Stabilization of NAD-dependent formate dehydrogenase from Candida boidinii by site-directed mutagenesis of cysteine residues. Eur J Biochem 267(5):1280–1289
Lutz J, Hollmann F, Ho TV, Schnyder A, Fish RH, Schmid A (2004) Bioorganometallic chemistry: biocatalytic oxidation reactions with biomimetic NAD+/NADH co-factors and [Cp*Rh(bpy)H]+ for selective organic synthesis. J Organomet Chem 689(25):4783–4790
Steckhan E, Herrmann S, Ruppert R, Dietz E, Frede M, Spika E (1991) Analytical study of a series of substituted (2,2′-bipyridyl)(pentamethylcyclopentadienyl)rhodium and iridium complexes with regard to their effectiveness as redox catalysts for the indirect electrochemical and chemical-reduction of NAD(P)+. Organometallics 10(5):1568–1577
Höllrigl V, Otto K, Schmid A (2007) Electroenzymatic asymmetric reduction of rac-3-methylcyclohexanone to (1S,3S)-3-methylcyclohexanol in organic/aqueous media catalyzed by a thermophilic alcohol dehydrogenase. Adv Synth Catal 349(8–9):1337–1340
Speiser B (1981) Elektroanalytische methoden II: cyclische voltammetrie. Chemie Unserer Zeit 15(2):62–67
Hamann CH, Vielstich W (1998) Elektrochemie, 3rd edn. Wiley, Weinheim
Lütz S, Rao N, Wandrey C (2006) Membranes in Biotechnology. Chem Eng Technol 29:1404–1415
Dreisbach C, Wischnewski G, Kragl U, Wandrey C (1995) Changes of enantioselectivity with the substrate ratio for the addition of diethylzinc to aldehydes using a catalyst coupled to a soluble polymer. J Chem Soc 7:875–878
Greiner L, Laue S, Liese A, Wandrey C (2006) Continuous homogeneous asymmetric transfer hydrogenation of ketones: lessons from kinetics. Chem Eur J 12(6):1818–1823
Kragl U, Dreisbach C (1996) Kontinuierliche asymmetrische synthese in einem membranreaktor. Angew Chem 108(6):684–685
Kragl U, Dwars T (2002) The development of new methods for the recycling of chiral catalysts. Trends Biotechnol 20(1):45–45
Liese A (2003) Biological principles applied to technical asymmetric catalysis. Habilitation, Rheinische Friedrich-Wilhelms-Universität, Bonn
Rissom S, Beliczey J, Giffels G, Kragl U, Wandrey C (1999) Asymmetric reduction of acetophenone in membrane reactors: comparison of oxazaborolidine and alcohol dehydrogenase catalysed processes. Tetrahedron Asymmetry 10(5):923–928
Woltinger J, Bommarius AS, Drauz K, Wandrey C (2001) The chemzyme membrane reactor in the fine chemicals industry. Org Process Res Dev 5(3):241–248
Woltinger J, Drauz K, Bommarius AS (2001) The membrane reactor in the fine chemicals industry. Appl Catal A 221(1-2):171–185
Vuorilehto K, Lütz S, Wandrey C (2004) Indirect electrochemical reduction of nicotinamide coenzymes. Bioelectrochemistry 65(1):1–7
van Deurzen MPJ, Seelbach K, van Rantwijk F, Kragl U, Sheldon RA (1997) Chloroperoxidase: use of a hydrogen peroxide-stat for controlling reactions and improving enzyme performance. Biocatal Biotransform 15(1):1–16
Hollmann F, Witholt B, Schmid A (2002) [Cp*Rh(bpy)(H2O)]2+: a versatile tool for efficient and non-enzymatic regeneration of nicotinamide and flavin coenzymes. J Mol Catal B Enzym 19:167–176
Steckhan E, Frede M, Herrmann S, Ruppert R, Spika E, Dietz E (1992) Enzymatische synthesen durch indirekte elektrochemische prozesse. DECHEMA-monographien, vol 125. VCH, Weinheim, pp 723–753
Greiner D, Kohlmann C, Leitner W, Lütz S, Wandrey C (2009) Procedure for the conversion of substrates e.g. organic sulfides, ketones and amino acids, to products by a combined electrochemical and catalytic process in a reaction medium containing ionic liquid. Patent DE102007044379 A1, 26 March 2009
Krieg T, Sydow A, Schroder U, Schrader J, Holtmann D (2014) Reactor concepts for bioelectrochemical syntheses and energy conversion. Trends Biotechnol 32(12):645–655
Min K, Park DH, Yoo YJ (2010) Electroenzymatic synthesis of L-DOPA. J Biotechnol 146(1–2):40–44
Varnicic M, Vidakovic-Koch T, Sundmacher K (2015) Gluconic acid synthesis in an electroenzymatic reactor. Electrochim Acta 176:1523–1523
Hildebrand F, Kohlmann C, Franz A, Lütz S (2008) Synthesis, characterization and application of new rhodium complexes for indirect electrochemical cofactor regeneration. Adv Synth Catal 350(6):909–918
Hofstetter K, Lutz J, Lang I, Witholt B, Schmid A (2004) Coupling of biocatalytic asymmetric epoxidation with NADH regeneration in organic-aqueous emulsions. Angew Chem 43(16):2163–2166
Ruinatscha R, Dusny C, Buehler K, Schmid A (2009) Productive asymmetric styrene epoxidation based on a next generation electroenzymatic methodology. Adv Synth Catal 351(14–15):2505–2515
Schmid A, Vereyken I, Held M, Witholt B (2001) Preparative regio- and chemoselective functionalization of hydrocarbons catalyzed by cell free preparations of 2-hydroxybiphenyl 3-monooxygenase. J Mol Catal B Enzym 11(4-6):455–462
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer International Publishing AG
About this chapter
Cite this chapter
Schmitz, L.M., Rosenthal, K., Lütz, S. (2017). Enzyme-Based Electrobiotechnological Synthesis. In: Harnisch, F., Holtmann, D. (eds) Bioelectrosynthesis. Advances in Biochemical Engineering/Biotechnology, vol 167. Springer, Cham. https://doi.org/10.1007/10_2017_33
Download citation
DOI: https://doi.org/10.1007/10_2017_33
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-03298-2
Online ISBN: 978-3-030-03299-9
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)