Wiring step-wise reactions with immobilized multi-enzyme systems

References

• Aissaoui N, Bergaoui L, Boujday S, Lambert JF, Méthivier C, Landoulsi J. 2014. Enzyme immobilization on silane-modified surface through short linkers: fate of interfacial phases and impact on catalytic activity. Langmuir 30:4066–4077.
   PubMed Web of Science ®Google Scholar
• Ba S, Haroune L, Cruz-Morató C, Jacquet C, Touahar IE, Bellenger JP, Legault CY, Jones JP, Cabana H. 2014. Synthesis and characterization of combined cross-linked laccase and tyrosinase aggregates transforming acetaminophen as a model phenolic compound in wastewaters. Sci Total Environ 487:748–755.
   PubMed Web of Science ®Google Scholar
• Barbosa O, Torres R, Ortiz C, Berenguer-Murcia A, Rodrigues RC, Fernandez-Lafuente R. 2013. Heterofunctional supports in enzyme immobilization: From traditional immobilization protocols to opportunities in tuning enzyme properties. Biomacromolecules 14:2433–2462.
   PubMed Web of Science ®Google Scholar
• Beauchamp J, Vieille C. 2015. Activity of select dehydrogenases with Sepharose-immobilized N(6)-carboxymethyl-NAD . Bioengineered 6:106–110.
   PubMed Web of Science ®Google Scholar
• Bučko M, Gemeiner P, Schenkmayerová A, Krajčovič T, Rudroff F, Mihovilovič MD. 2016. Baeyer-Villiger oxidations: biotechnological approach. Appl Microbiol Biotechnol 100:6585–6599.
   PubMed Web of Science ®Google Scholar
• Chado GR, Stoykovich MP, Kaar JL. 2016. Role of dimension and spatial arrangement on the activity of biocatalytic cascade reactions on scaffolds. ACS Catal 6:5161–5169.
   Web of Science ®Google Scholar
• Chung J, Hwang ET, Kim JH, Kim BC, Gu MB. 2014. Modular multi-enzyme cascade process using highly stabilized enzyme microbeads. Green Chem 16:1163–1167.
   Web of Science ®Google Scholar
• Dubey NC, Tripathi BP, Müller M, Stamm M, Ionov L. 2016. Bienzymatic sequential reaction on microgel particles and their cofactor dependent applications. Biomacromolecules 17:1610–1620.
   PubMed Web of Science ®Google Scholar
• Eguílaz M, Villalonga R, Yáñez-Sedeño P, Pingarrón JM. 2011. Designing electrochemical interfaces with functionalized magnetic nanoparticles and wrapped carbon nanotubes as platforms for the construction of high-performance bienzyme biosensors. Anal Chem 83:7807–7814.
   PubMed Web of Science ®Google Scholar
• El-Zahab B, Donnelly D, Wang P. 2008. Particle-tethered NADH for production of methanol from CO(2) catalyzed by coimmobilized enzymes. Biotechnol Bioeng 99:508–514.
   PubMed Web of Science ®Google Scholar
• El-Zahab B, Jia H, Wang P. 2004. Enabling multienzyme biocatalysis using nanoporous materials. Biotechnol Bioeng 87:178–183.
   PubMed Web of Science ®Google Scholar
• Fessner WD. 2015. Systems Biocatalysis: development and engineering of cell-free 'artificial metabolisms' for preparative multi-enzymatic synthesis. New Biotechnol 32:658–664.
   PubMed Web of Science ®Google Scholar
• Fu J, Liu M, Liu Y, Woodbury NW, Yan H. 2012. Interenzyme substrate diffusion for an enzyme cascade organized on spatially addressable DNA nanostructures. J Am Chem Soc 134:5516–5519.
   PubMed Web of Science ®Google Scholar
• Fu J, Yang YR, Johnson-Buck A, Liu M, Liu Y, Walter NG, Woodbury NW, Yan H. 2014. Multi-enzyme complexes on DNA scaffolds capable of substrate channelling with an artificial swinging arm. Nat Nanotechnol 9:531–536.
   PubMed Web of Science ®Google Scholar
• Gao H, Khera E, Lee JK, Wen F. 2016. Immobilization of multi-biocatalysts in alginate beads for cofactor regeneration and improved reusability. J Vis Exp 110:e53944. doi: 10.3791/53944
   Google Scholar
• Gao X, Ni K, Zhao C, Ren Y, Wei D. 2014. Enhancement of the activity of enzyme immobilized on polydopamine-coated iron oxide nanoparticles by rational orientation of formate dehydrogenase. J Biotechnol 188:36–41.
   PubMed Web of Science ®Google Scholar
• Gao X, Zhao C, Yu T, Yang S, Ren Y, Wei D. 2015. Construction of a reusable multi-enzyme supramolecular device via disulfide bond locking. Chem Commun (Camb.) 51:10131–10133.
   PubMed Web of Science ®Google Scholar
• Haga T, Hirakawa H, Nagamune T. 2013. Fine tuning of spatial arrangement of enzymes in a PCNA-mediated multienzyme complex using a rigid poly-L-proline linker. PLoS One 8:e75114. doi: 10.1371/journal.pone.0075114
   PubMed Web of Science ®Google Scholar
• Heidepriem PM, Kohl HH, Riedman ME. 1980. Immobilization of several multienzyme systems on porous glass beads. J Solid-Phase Biochem 5:5–9.
   Google Scholar
• Hirano K, Kurosaki M, Nihei S, Hasegawa H, Shinoda S, Haruki M, Hirano N. 2016. Enzymatic diversity of the Clostridium thermocellum cellulosome is crucial for the degradation of crystalline cellulose and plant biomass. Sci Rep 6:35709. doi: 10.1038/srep35709
   PubMed Web of Science ®Google Scholar
• Hollmann F, Arends IWCE, Buehler K. 2010. Biocatalytic redox reactions for organic synthesis: nonconventional regeneration methods. ChemCatChem 2:762–782.
   Web of Science ®Google Scholar
• Huang X, Li M, Mann S. 2014. Membrane-mediated cascade reactions by enzyme-polymer proteinosomes. Chem Commun (Camb.) 50:6278–6280.
   PubMed Web of Science ®Google Scholar
• Idan O, Hess H. 2013. Origins of activity enhancement in enzyme cascades on scaffolds. ACS Nano 7:8658–8665.
   PubMed Web of Science ®Google Scholar
• Ji Q, Wang B, Tan J, Zhu L, Li L. 2016. Immobilized multienzymatic systems for catalysis of cascade reactions. Process Biochem 51:1193–1203.
   Web of Science ®Google Scholar
• Ji X, Su Z, Wang P, Ma G, Zhang S. 2014a. Polyelectrolyte doped hollow nanofibers for positional assembly of bienzyme system for cascade reaction at O/W interface. ACS Catal 4:4548–4559.
   Web of Science ®Google Scholar
• Ji X, Su Z, Wang P, Ma G, Zhang S. 2015. Tethering of nicotinamide adenine dinucleotide inside hollow nanofibers for high-yield synthesis of methanol from carbon dioxide catalyzed by coencapsulated multienzymes. ACS Nano 9:4600–4610.
   PubMed Web of Science ®Google Scholar
• Ji X, Wang P, Su Z, Ma G, Zhang S. 2014b. Enabling multi-enzyme biocatalysis using coaxial-electrospun hollow nanofibers: redesign of artificial cells. J Mater Chem B 2:181–190.
   Web of Science ®Google Scholar
• Jia F, Mallapragada SK, Narasimhan B. 2015. Multienzyme immobilization and colocalization on nanoparticles enabled by DNA hybridization. Ind Eng Chem Res 54:10212–10220.
   Web of Science ®Google Scholar
• Jia F, Narasimhan B, Mallapragada S. 2014. Materials-based strategies for multi-enzyme immobilization and co-localization: a review. Biotechnol Bioeng 111:209–222.
   PubMed Web of Science ®Google Scholar
• Kang W, Liu J, Wang J, Nie Y, Guo Z, Xia J. 2014. Cascade biocatalysis by multienzyme-nanoparticle assemblies. Bioconjug Chem 25:1387–1394.
   PubMed Web of Science ®Google Scholar
• Köhler V, Turner NJ. 2014. Artificial concurrent catalytic processes involving enzymes. Chem Commun (Camb.) 51:450–464.
   PubMed Web of Science ®Google Scholar
• Küchler A, Yoshimoto M, Luginbühl S, Mavelli F, Walde P. 2016. Enzymatic reactions in confined environments. Nat Nanotechnol 11:409–420.
   PubMed Web of Science ®Google Scholar
• Li Z, Zhang Y, Su Y, Ouyang P, Ge J, Liu Z. 2014. Spatial co-localization of multi-enzymes by inorganic nanocrystal-protein complexes. Chem Commun (Camb.) 50:12465–12468.
   PubMed Web of Science ®Google Scholar
• Liu W, Wang P. 2007. Cofactor regeneration for sustainable enzymatic biosynthesis. Biotechnol Adv 25:369–384.
   PubMed Web of Science ®Google Scholar
• Liu W, Zhang S, Wang P. 2009. Nanoparticle-supported multi-enzyme biocatalysis with in situ cofactor regeneration. J Biotechnol 139:102–107.
   PubMed Web of Science ®Google Scholar
• Logan TC, Clark DS, Stachowiak TB, Svec F, Fréchet JMJ. 2007. Photopatterning enzymes on polymer monoliths in microfluidic devices for steady-state kinetic analysis and spatially separated multi-enzyme reactions. Anal Chem 79:6592–6598.
   PubMed Web of Science ®Google Scholar
• Luo J, Meyer AS, Mateiu RV, Pinelo M. 2015. Cascade catalysis in membranes with enzyme immobilization for multi-enzymatic conversion of CO2 to methanol. New Biotechnol 32:319–327.
   PubMed Web of Science ®Google Scholar
• Mahdi R, Guérard-Hélaine C, Prévot V, deBerardinis V, Forano C, Lemaire M. 2015. Design of artificial metabolisms in layered nanomaterials for the enzymatic synthesis of phosphorylated sugars. ChemCatChem 7:3110–3115.
   Web of Science ®Google Scholar
• Mallin H, Wulf H, Bornscheuer UT. 2013. A self-sufficient Baeyer-Villiger biocatalysis system for the synthesis of ɛ-caprolactone from cyclohexanol. Enzyme Microb Technol 53:283–287.
   PubMed Web of Science ®Google Scholar
• Mateo C, Grazu V, Palomo JM, Lopez-Gallego F, Fernandez-Lafuente R, Guisan JM. 2007. Immobilization of enzymes on heterofunctional epoxy supports. Nat Protoc 2:1022–1033.
   PubMed Web of Science ®Google Scholar
• Meeuwissen SA, Rioz-Martínez A, De Gonzalo G, Fraaije MW, Gotor V, Van Hest JCM. 2011. Cofactor regeneration in polymersome nanoreactors: enzymatically catalysed Baeyer-Villiger reactions. J Mater Chem 21:18923–18926.
   Web of Science ®Google Scholar
• Ngo TA, Nakata E, Saimura M, Morii T. 2016. Spatially organized enzymes drive cofactor-coupled cascade reactions. J Am Chem Soc 138:3012–3021.
   PubMed Web of Science ®Google Scholar
• Obert R, Dave BC. 1999. Enzymatic conversion of carbon dioxide to methanol: enhanced methanol production in silica sol-gel matrices [5]. J Am Chem Soc 121:12192–12193.
   Web of Science ®Google Scholar
• Ottolina G, Carrea G, Riva S, Bückmann AF. 1990. Coenzymatic properties of low molecular-weight and macromolecular N6-derivatives of NAD + and NADP + with dehydrogenases of interest for organic synthesis. Enzyme Microb Technol 12:596–602.
   PubMed Web of Science ®Google Scholar
• Paul CE, Hollmann F. 2016. A survey of synthetic nicotinamide cofactors in enzymatic processes. Appl Microbiol Biotechnol 100:4773–4778.
   PubMed Web of Science ®Google Scholar
• Peirce S, Virgen-Ortíz JJ, Tacias-Pascacio VG, Rueda N, Bartolome-Cabrero R, Fernandez-Lopez L, Russo ME, Marzocchella A, Fernandez-Lafuente R. 2016. Development of simple protocols to solve the problems of enzyme coimmobilization. Application to coimmobilize a lipase and a β-galactosidase. RSC Adv 6:61707–61715.
   Web of Science ®Google Scholar
• Pescador P, Katakis I, Toca-Herrera JL, Donath E. 2008. Efficiency of a bienzyme sequential reaction system immobilized on polyelectrolyte multilayer-coated colloids. Langmuir 24:14108–14114.
   PubMed Web of Science ®Google Scholar
• Roberts CC, Chang CEA. 2015. Modeling of enhanced catalysis in multienzyme nanostructures: Effect of molecular scaffolds, spatial organization, and concentration. J Chem Theory Comput 11:286–292.
   PubMed Web of Science ®Google Scholar
• Rocha-Martin J, Acosta A, Guisan JM, Lõpez-Gallego F. 2015. Immobilizing systems biocatalysis for the selective oxidation of glycerol coupled to insitu cofactor recycling and hydrogen peroxide elimination. ChemCatChem 7:1939–1947.
   Web of Science ®Google Scholar
• Rocha-Martín J, Rivas BL, Muñoz R, Guisán JM, López-Gallego F. 2012. Rational co-immobilization of bi-enzyme cascades on porous supports and their applications in bio-redox reactions with insitu recycling of soluble cofactors. ChemCatChem 4:1279–1288.
   Web of Science ®Google Scholar
• Rocha-Martin J, Velasco-Lozano S, Guisán JM, López-Gallego F. 2014. Oxidation of phenolic compounds catalyzed by immobilized multi-enzyme systems with integrated hydrogen peroxide production. Green Chem 16:303–311.
   Web of Science ®Google Scholar
• Rodríguez-Alonso MJ, Rodríguez-Vico F, Las Heras-Vázquez FJ, Clemente-Jiménez JM. 2016. Immobilization of a multi-enzyme system for L-amino acids production. J Chem Technol Biotechnol 91:1972–1981.
   Web of Science ®Google Scholar
• Rollin JA, Tam TK, Zhang YHP. 2013. New biotechnology paradigm: cell-free biosystems for biomanufacturing. Green Chem 15:1708–1719.
   Web of Science ®Google Scholar
• Schmidt-Dannert C, Lopez-Gallego F. 2016. A roadmap for biocatalysis: functional and spatial orchestration of enzyme cascades. Microb Biotechnol 9:601–609.
   PubMed Web of Science ®Google Scholar
• Schmidt S, Genz M, Balke K, Bornscheuer UT. 2015. The effect of disulfide bond introduction and related Cys/Ser mutations on the stability of a cyclohexanone monooxygenase. J Biotechnol 214:199–211.
   PubMed Web of Science ®Google Scholar
• Schoffelen S, Van Hest JCM. 2012. Multi-enzyme systems: bringing enzymes together in vitro. Soft Matter 8:1736–1746.
   Web of Science ®Google Scholar
• Sun J, Ge J, Liu W, Lan M, Zhang H, Wang P, Wang Y, Niu Z. 2014. Multi-enzyme co-embedded organic-inorganic hybrid nanoflowers: synthesis and application as a colorimetric sensor. Nanoscale 6:255–262.
   PubMed Web of Science ®Google Scholar
• Tan CY, Hirakawa H, Suzuki R, Haga T, Iwata F, Nagamune T. 2016. Immobilization of a bacterial cytochrome P450 monooxygenase system on a solid support. Angew Chem 128:15226–15230.
   Google Scholar
• Truppo MD. 2012. 7.4 cofactor recycling for enzyme catalyzed processes. In: Comprehensive Chirality. Vol. 7. Amsterdam: Elsevier. p. 46–70.
   Google Scholar
• Van Dongen SFM, Nallani M, Cornelissen JJLM, Nolte RJM, Van Hest JCM. 2009. A three-enzyme cascade reaction through positional assembly of enzymes in a polymersome nanoreactor. Chem Eur J 15:1107–1114.
   PubMed Web of Science ®Google Scholar
• Van Rantwijk F, Stolz A. 2015. Enzymatic cascade synthesis of (S)-2-hydroxycarboxylic amides and acids: cascade reactions employing a hydroxynitrile lyase, nitrile-converting enzymes and an amidase. J Mol Catal B: Enzym 114:25–30.
   Web of Science ®Google Scholar
• Velasco-Lozano S, Benítez-Mateos AI, López-Gallego F. 2016a. Co-immobilized phosphorylated cofactors and enzymes as self-sufficient heterogeneous biocatalysts for chemical processes. Angew Chem Int Edit 56:771–775.
   PubMed Web of Science ®Google Scholar
• Velasco-Lozano S, Rocha-Martin J, Favela-Torres E, Calvo J, Berenguer J, Guisán JM, López-Gallego F. 2016b. Hydrolysis and oxidation of racemic esters into prochiral ketones catalyzed by a consortium of immobilized enzymes. Biochem Eng J 112:136–142.
   Web of Science ®Google Scholar
• Wheeldon I, Minteer SD, Banta S, Barton SC, Atanassov P, Sigman M. 2016. Substrate channelling as an approach to cascade reactions. Nat Chem 8:299–309.
   PubMed Web of Science ®Google Scholar
• You C, Zhang YHP. 2013. Self-assembly of synthetic metabolons through synthetic protein scaffolds: one-step purification, co-immobilization, and substrate channeling. ACS Synthetic Biol 2:102–110.
   PubMed Web of Science ®Google Scholar
• Yuan J, Mishra P, Ching CB. 2017. Engineering the leucine biosynthetic pathway for isoamyl alcohol overproduction in Saccharomyces cerevisiae. J Ind Microbiol Biotechnol 4:107–117.
   Google Scholar
• Zheng M, Zhang S, Ma G, Wang P. 2011. Effect of molecular mobility on coupled enzymatic reactions involving cofactor regeneration using nanoparticle-attached enzymes. J Biotechnol 154:274–280.
   PubMed Web of Science ®Google Scholar
• Zhu Z, Kin Tam T, Sun F, You C, Percival Zhang YH. 2014. A high-energy-density sugar biobattery based on a synthetic enzymatic pathway. Nature Commun 5:3026. doi: 10.1038/ncomms4026
   PubMed Web of Science ®Google Scholar