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Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water.

A recombinant enoate reductase was expressed in cyanobacteria and used for the light-catalyzed, enantioselective reduction of C=C bonds. The coupling of oxidoreductases to natural photosynthesis allows asymmetric syntheses fueled by the oxidation of water. Bypassing the addition of sacrificial cosubstrates as electron donors significantly improves the atom efficiency and avoids the formation of undesired side products. Crucial factors for product formation are the availability of NADPH and the amount of active enzyme in the cells. The efficiency of the reaction is comparable to typical whole-cell biotransformations in E. coli. Under optimized conditions, a solution of 100 mg prochiral 2-methylmaleimide was reduced to optically pure 2-methylsuccinimide (99 % ee, 80 % yield of isolated product). High product yields and excellent optical purities demonstrate the synthetic usefulness of light-catalyzed whole-cell biotransformations using recombinant cyanobacteria.

Köninger K, Gómez Baraibar Á, Mügge C, Paul CE, Hollmann F, Nowaczyk MM, Kourist R (2016) Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water. Angew Chem Int Ed DOI: 10.1002/anie.201601200

Press Release: http://aktuell.ruhr-uni-bochum.de/pm2016/pm00043.html.en

Publications

2017

  • Zhao F, Plumeré N, Nowaczyk MM, Ruff A, Schuhmann W, Conzuelo F (2017) Interrogation of a PS1-based Photocathode by Means of Scanning Photoelectrochemical Microscopy Small DOI
  • Essmann V, Zhao F, Hartmann V, Nowaczyk MM, Schuhmann W, Conzuelo F (2017) In operando investigation of electrically coupling of photosystem 1 and photosystem 2 by means of bipolar electrochemistry Analytical Chemistry DOI
  • Zhao F, Conzuelo F, Hartmann V, Li H, Stapf S, Nowaczyk MM, Rögner M, Plumeré N, Lubitz W, Schuhmann W (2017) A novel versatile microbiosensor for local hydrogen detection by means of scanning photoelectrochemical microscopy Biosensors and Bioelectronics 94, 433-437 DOI

2016

  • Nowaczyk MM and Plumeré N (2016) Photosynthesis: Short Circuit at the Chlorophyll - News and Views in Nature Chemical Biology 12:990-991 DOI
  • Nowaczyk MM and Kourist R (2016) Lichtgetriebene Ganzzell-biotransformation mit rekombinanten Cyanobakterien Biospektrum 22:765 DOI
  • Ziehe D, Dünschede B, Zenker M, Funke S, Nowaczyk MM, Schünemann D (2016) The chloroplast SRP systems of charophytes and bryophytes as intermediates in the evolution of SRP-dependent protein transport in higher plants PLoS One PLoS One 11:e0166818 DOI
  • Calow J, Behrens AJ, Mader S, Bockau U, Struwe WB, Harvey DJ, Cormann KU, Nowaczyk MM, Loser K, Schinor D, Hartmann MWW, Crispin M (2016) Antibody production using a ciliate generates unusual antibody glycoforms displaying enhanced cell-killing activity MAbs 8:1498-1511 DOI
  • Heinz S, Rast A, Shao L, Gutu A, Gügel IL, Heyno E, Labs M, Rengstl B, Viola S, Nowaczyk MM, Leister D, Nickelsen J (2016) Thylakoid Membrane Architecture in Synechocystis Depends on CurT, a Homolog of the Granal CURVATURE THYLAKOID1 Proteins Plant Cell 28:2238-2260 DOI
  • Sokol KP, Mersch D, Hartmann V, Zhang JZ, Nowaczyk MM, Rögner M, Ruff A, Schuhmann W, Plumeré N, Reisner E (2016) Rational wiring of photosystem II to hierarchical indium tin oxide electrodes using redox polymers Energy Environ Sci 9:3698-3709 [cover] DOI
  • Köninger K, Gómez Baraibar Á, Mügge C, Paul CE, Hollmann F, Nowaczyk MM, Kourist R (2016) Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water Angew Chem Int Ed 55:5582-5585 DOI
  • Cormann KU, Möller M, Nowaczyk MM (2016) Critical assessment of protein cross-linking and molecular docking: an updated model for the interaction between photosystem II and Psb27 Front Plant Sci 7:157 DOI
  • Vöpel T, Saw EN, Hartmann V, Williams R, Müller F, Schuhmann W, Plumeré N, Nowaczyk M, Ebbinghaus S, Rögner M (2016) Simultaneous measurements of photocurrents and H2O2 evolution from solvent exposed Photosystem 2 complexes Biointerphases 11:019001 DOI
  • Heinz S, Liauw P, Nickelsen J, Nowaczyk M (2016) Analysis of photosystem II biogenesis in cyanobacteria BBA Bioenergetics 1857:274-287 DOI
  • Korste A, Wulfhorst H, Ikegami T, Nowaczyk MM, Stoll R (2016) NOE distance and dihedral angle restraints to calculate the solution structure of the NDH-1 complex subunit CupS from Thermosynechococcus elongatus Data in brief 6:249-252 DOI
  • Plumeré N and Nowaczyk MM (2016) Biophotoelectrochemistry of Photosynthetic Proteins DOI

2015

  • Mutoh R, Muraki N, Shinmura K, Kubota-Kawai H, Lee YH, Nowaczyk MM, Rögner M, Hase T, Ikegami T, Kurisu G (2015) X-ray Structure and Nuclear Magnetic Resonance Analysis of the Interaction Sites of the Ga-substituted Cyanobacterial Ferredoxin Biochemistry 54:6052-6061 DOI
  • Zhao F, Conzuelo F, Hartmann V, Li H, Nowaczyk MM, Plumeré N, Rögner M, Schuhmann W (2015) Light Induced H2 Evolution from a Biophotocathode Based on Photosystem 1 - Pt Nanoparticles Complexes Integrated in Solvated Redox Polymers Films J Phys Chem B 119:13726-31 DOI
  • Korste A, Wulfhorst H, Ikegami T, Nowaczyk MM, Stoll R (2015) Solution structure of the NDH-1 complex subunit CupS from Thermosynechococcus elongatus BBA Bioenergetics1847:1212-1221 DOI
  • Bartsch M, Gassmeyer SK, Köninger K, Igarashi K, Liauw P, Dyczmons-Nowaczyk N, Miyamoto K, Nowaczyk MM, Kourist R (2015) Photosynthetic production of enantioselective biocatalysts Microb Cell Fact 14:53 DOI
  • Liauw P, Kannchen D, Gasper R, Dyczmons-Nowaczyk N, Nowaczyk MM, Hofmann E (2015) Cloning, expression, crystallization and preliminary X-ray studies of a superfolder GFP fusion of cyanobacterial Psb32 Acta Cryst F 71:409-413 DOI
  • Walter B, Hristou A, Nowaczyk MM, Schünemann D (2015) In vitro reconstitution of cotranslational D1 insertion reveals a role of the cpSec/Alb3 translocase and Vipp1 in photosystem II biogenesis Biochem J 468: 315-324 DOI
  • Korste A, Wulfhorst H, Ikegami T, Nowaczyk MM, Stoll R (2015) 1H, 13C and 15N chemical shift assignments of the NDH-1 complex subunit CupS. Biomol NMR Assign 9:169-171 DOI
  • Nowaczyk MM, Rexroth S, Rögner M (2015) Biotechnological Potential of Cyanobacteria DOI

2014

  • Corman KU, Bartsch M, Rögner M, Nowaczyk MM (2014) Localization of the CyanoP binding site on photosystem II by surface plasmon resonance spectroscopy. Front Plant Sci 5:595 DOI
  • Wulfhorst H, Franken LE, Wessinghage T, Boekema EJ, Nowaczyk MM (2014) The 5 kDa Protein NdhP Is Essential for Stable NDH-1L Assembly in Thermosynechococcus elongatus. PLoS One 9:e103584 DOI
  • Rexroth S, Rexroth D, Veit S, Plohnke N, Cormann KU, Nowaczyk MM, Rögner M (2014) Functional Characterization of the Small Regulatory Subunit PetP from the Cytochrome b6f Complex in Thermosynechococcus elongatus. Plant Cell 26:3435-3448 DOI
  • Hartmann V, Kothe T, Pöller S, El-Mohsnawy E, Nowaczyk MM, Plumere N, Schuhmann W, Rögner M (2014) Redox hydrogels with adjusted redox potential for improved efficiency in Z-scheme inspired biophotovoltaic cells. Phys Chem Chem Phys 16:11936-11941 DOI
  • Lohmiller T, Krewald V, Pérez Navarro M, Retegan M, Rapatskiy L, Nowaczyk MM, Boussac A, Neese F, Lubitz W, Pantazis DA, Ames WM, Cox N (2014) Structure, ligands and substrate coordination of the oxygen-evolving complex of photosystem II in the S2 state: a combined EPR and DFT study. Phys Chem Chem Phys 16:11877-11892 DOI

2013

  • Kothe T, Plumeré N, Badura A, Nowaczyk MM, Guschin DA, Rögner M, Schuhmann W (2013) Combination of a Photosystem 1-Based Photocathode and a Photosystem 2-Based Photoanode to a Z-Scheme Mimic for Biophotovoltaic Applications. Angew Chem Int Ed 52:14233-14236 DOI
  • Pérez Navarro M, Ames WM, Nilsson H, Lohmiller T, Pantazis DA, Rapatskiy L, Nowaczyk MM, Neese F, Boussac A, Messinger J, Lubitz W, Cox N (2013) Ammonia binding to the oxygen-evolving complex of photosystem II identifies the solvent-exchangeable oxygen bridge (µ-oxo) of the manganese tetramer. Proc Natl Acad Sci USA 110:15561-15567 DOI

2012

  • Rapatskiy L, Cox N, Savitsky A, Ames WM, Sander J, Nowaczyk MM, Rögner M, Boussac A, Neese F, Messinger J, Lubitz W (2012) Detection of the Water Binding Sites of the Oxygen-evolving Complex of Photosystem II Using W-band (17)O ELDOR-detected NMR Spectroscopy. J Am Chem Soc 134:16619-16653 DOI
  • Nowaczyk MM, Krause K, Mieseler M, Sczibilanski A, Ikeuchi, M, Rögner M (2012) Deletion of psbJ leads to accumulation of Psb27–Psb28 photosystem II complexes in Thermosynechococcus elongatus. BBA Bioenergetics 1817:1339-1345 DOI

2011

  • Grasse N, Mamedov F, Becker K, Styring S, Rögner M, Nowaczyk MM (2011) The role of a novel dimeric Photosystem II-Psb27 complex in PSII repair. J Biol Chem 286:29548-29555 DOI
  • Becker K, Cormann KU, Nowaczyk MM (2011) Assembly of the water-oxidizing complex in photosystem II. J Photochem Photobiol B 104:204-11 DOI
  • Nowaczyk MM, Wulfhorst H, Ryan CM, Souda P, Zhang H, Cramer WA, Whitelegge JP (2011) NdhP and NdhQ: two novel small subunits of the cyanobacterial NDH-1 complex. Biochemistry 50:1121-1125 DOI

2010

  • El-Mohsnawy E, Kopczak MJ, Schlodder E, Nowaczyk M, Meyer HE, Warscheid B, Karapetyan NV, Rögner M (2010) Structure and Function of Intact Photosystem 1 Monomers from the Cyanobacterium Thermosynechococcus elongatus. Biochemistry 49:4740-4751 DOI
  • Sander J, Nowaczyk M, Buchta J, Dau H, Vass I, Deak Z, Dorogi M, Iwai M, Roegner M (2010) Functional characterization and quantification of the alternative PsbA copies in Thermosynechococcus elongatus and their role in photoprotection. J Biol Chem 285:29851-29856 DOI
  • Nowaczyk MM, Sander J, Grasse N, Cormann KU, Gomolla D, Bernat G, Rögner M (2010) Dynamics of the cyanobacterial photosynthetic network: Communication and modification of membrane protein complexes. Eur J Cell Biol 89:974-982 DOI

2009

  • Szczepaniak M, Sander J, Nowaczyk M, Müller MG, Rögner M, Holzwarth AR (2009) Charge separation, stabilization, and protein relaxation in photosystem II core particles with closed reaction center. Biophys J 96:621-31 DOI
  • Cormann KU, Bangert JA, Ikeuchi M, Rögner M, Stoll R, Nowaczyk MM (2009) Structure of Psb27 in solution: implications for transient binding to Photosystem II during biogenesis and repair. Biochemistry 48:8768-70 DOI
  • Cormann KU, Ikeuchi M, Rögner M, Nowaczyk MM, Stoll R (2009) Sequence-specific 1H, 13C, and 15N backbone assignment of Psb27 from Synechocystis PCC 6803. Biomol NMR Assign 3:247-9 DOI
  • Schottkowski M, Ratke J, Oster U, Nowaczyk M, Nickelsen J (2009) Pitt, a Novel Tetratricopeptide Repeat Protein Involved in Light-Dependent Chlorophyll Biosynthesis and Thylakoid Membrane Biogenesis in Synechocystis sp PCC 6803. Mol Plant 2:1289-1297 DOI

2008

  • Folea IM, Zhang P, Nowaczyk MM, Ogawa T, Aro EM, Boekema EJ (2008) Single particle analysis of thylakoid proteins from Thermosynechococcus elongatus and Synechocystis 6803: localization of the CupA subunit of NDH-1. FEBS Lett 582:249-54 DOI
  • Martinez-Junza V, Szczepaniak M, Braslavsky SE, Sander J, Nowaczyk M, Rögner M, Holzwarth AR (2008) A photoprotection mechanism involving the D(2) branch in photosystem II cores with closed reaction centers. Photochem Photobiol Sci 7:1337-43 DOI

2007

  • Mamedov F, Nowaczyk MM, Thapper A, Rögner M, Styring S (2007) Functional Characterization of Monomeric Photosystem II Core Preparations from Thermosynechococcus elongatus with or without the Psb27 Protein. Biochemistry 46:5542-5551 DOI
  • Klinkert B, Nowaczyk MM, Nickelsen J (2007) Function of Genetic Material: Assembly Factors of the Photosynthetic Machinery in Cyanobacteria. Progress in Botany (Esser K, Lüttge U, Beyschlag W, Murata J, eds) 68: 57-79 DOI

2006

  • Milaslavina Y, Szczepaniak M, Müller MG, Sander J, Nowaczyk M, Rögner M, Holzwarth, AR (2006) Charge separation kinetics in intact photosystem II core particles is traplimited. A picosecond fluorescence study. Biochemistry 45:2436-2442 DOI
  • Holzwarth AR, Müller MG, Reus M, Nowaczyk M, Sander J, Rögner M (2006) Mechanism of electron transfer in intact photosystem II and in isolated reaction centers. Pheophytin is the primary electron acceptor. Proc Natl Acad Sci USA 103:6895-6900 DOI
  • Nowaczyk MM, Hebeler R, Schlodder E, Meyer HE, Warscheid B, Rögner M (2006) Psb27, a Cyanobacterial Lipoprotein, Is Involved in the Repair Cycle of Photosystem II. Plant Cell 18:3121-3131 DOI
  • Nowaczyk M, Berghaus C, Steinhoff,H-J, Stoll R, Rögner M (2006) Preliminary NMR and EPR studies of the 33 kDa protein (PsbO) in solution. Essays on Science (Rashid S, ed), Hamdard Foundation, Pakistan, 184-196

2005

  • Arteni AA, Nowaczyk M, Lax J, Kouril R, Rögner M, Boekema EJ (2005) Single particle electron microscopy in combination with mass spectrometry to investigate novel complexes of membrane proteins. J Struct Biol 149:325-331 DOI
  • Nowaczyk M, Steinhoff H-J, Rögner M (2005) EPR-spectroscopy of spin-labeled PsbO from Thermosynechococcus elongatus. Photosynthesis: Fundamental Aspects to Global Perspectives" (van der Est A and Bruce D, eds) 246-248

2004

  • Nowaczyk M, Berghaus C, Stoll R, Rögner M (2004) Preliminary structural characterisation of the 33 kDa protein (PsbO) in solution studied by site-directed mutagenesis and NMR spectroscopy. Phys Chem Chem Phys 6:4878-4881 DOI
  • Nowaczyk M, Ambill M, Lax J, Prodöhl A, Oworah-Nkruma R, Rögner M (2004) Biochemical Analysis of a new 'His-Tag' PS2-Preparation from Thermosynechococcus elongatus. Cell Mol Biol Lett 9:79
  • Nowaczyk M, Oworah-Nkruma R, Rögner M, Popot JL (2004) Amphipols: Strategies For an Improved PS2 Environment in Aqueous Solution. Biohydrogen III (Miyake J, Igarashi Y, Rögner M, eds) 151-159 DOI

 

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