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• Enzymatic Activation Of Alkanes Constraints And Prospects Ukulele
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Abstract

Methane monooxygenases (MMOs) mediate the facile conversion of methane into methanol in methanotrophic bacteria with high efficiency under ambient conditions. Because the selective oxidation of methane is extremely challenging, there is considerable interest in understanding how these enzymes carry out this difficult chemistry. The impetus of these efforts is to learn from the microbes to develop a biomimetic catalyst to accomplish the same chemical transformation. Here, we review the progress made over the past two to three decades toward delineating the structures and functions of the catalytic sites in two MMOs: soluble methane monooxygenase (sMMO) and particulate methane monooxygenase (pMMO). sMMO is a water-soluble three-component protein complex consisting of a hydroxylase with a nonheme diiron catalytic site; pMMO is a membrane-bound metalloenzyme with a unique tricopper cluster as the site of hydroxylation. The metal cluster in each of these MMOs harnesses O₂ to functionalize the C—H bond using different chemistry. We highlight some of the common basic principles that they share. Finally, the development of functional models of the catalytic sites of MMOs is described. These efforts have culminated in the first successful biomimetic catalyst capable of efficient methane oxidation without overoxidation at room temperature.

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Enzymatic Activation Of Alkanes Constraints And Prospects Ukulele

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Enzymatic Activation Of Alkanes Constraints And Prospects Uk 2016

• Abels, C.; Carstensen, F.; Wessling, M.
• Methane partial oxidation by unsupported and silica supported iron phosphate catalysts—influence of reaction conditions and co-feeding of water on activity and selectivity

  Alptekin, G.O.; Herring, A.M.; Williamson, D.L.; Ohno, T.R.; McCormick, R.L.
• Anthony, C.
• Selective hydroxylation of benzene derivatives and alkanes with hydrogen peroxide catalysed by a manganese complex incorporated into mesoporous silica-alumina
• Cofactor-independent oxygenation reactions catalyzed by soluble methane monooxygenase at the surface of a modified gold electrode

  Astier, Y.; Balendra, S.; Hill, H.A.O.; Smith, T.J.; Dalton, H.
• Enzymatic activation of alkanes: constraints and prospective
• Mild, aqueous, aerobic, catalytic oxidation of methane to methanol and acetaldehyde catalyzed by a supported bipyrimidinylplatinum-polyoxometalate hybrid compound
• Elucidating membrane surface properties for preventing fouling of bioreactor membranes by surfactin

  Behary, N.; Lecouturier, D.; Perwuelz, A.; Dhulster, P.
• Direct oxidation of methane to oxygenates over heteropolyanions

  Benlounes, O.; Mansouri, S.; Rabia, C.; Hocine, S.
• Structure and catalytic properties of VOx/MCM materials for the partial oxidation of methane to formaldehyde

  Berndt, H.; Martin, A.; Bruckner, A.; Schreier, E.; Muller, D.; Kosslick, H.; Wolf, G.U.; Lucke, B.
• Production of primary aliphatic-alcohols with a recombinant Pseudomonas strain, encoding the alkane hydroxylase enzyme-system

  Bosetti, A.; van Beilen, J.B.; Preusting, H.; Lageveen, R.G.; Witholt, B.
• The methanotrophs − the families methylococcaceae and methylocystaceeae
• Bacterial dry matter content and biomass estimations
• Methane as raw material in synthetic chemistry: the final frontier
• Utilizing terminal oxidants to achieve P450-Catalyzed oxidation of methane
• Directed Evolution of Cytochrome P450 for Small Alkane Hydroxylation. Thesis
• Oxygen transfer in hydrocarbon-aqueous dispersions and its applicability to alkane bioprocesses: a review
• Envisioning the bioconversion of methane to liquid fuels
• Kinetic characterization of the soluble butane monooxygenase from Thauera butanivorans, formerly ‘ Pseudomonas butanovora ’

  Cooley, R.B.; Dubbel, B.L.; Sayavedra-Soto, L.A.; Bottomley, P.J.; Arp, D.J.
• Green oxidation of fatty alcohols: challenges and opportunities

  Cortes Corberan, V.; Gonzalez-Perez, M.E.; Martinez-Gonzalez, S.; Gomez-Aviles, A.
• High-rate conversion of methane to methanol by Methylosinus trichosporium OB3b
• Butane monooxygenase of ‘ Pseudomonas butanovora ': purification and biochemical characterization of a terminal-alkane hydroxylating diiron monooxygenase
• Regio- and stereoselectivity of particulate methane monooxygenase from Methylococcus capsulatus (Bath)

  Elliott, S.J.; Zhu, M.; Tso, L.; Nguyen, H.H.T.; Yip, J.H.K.; Chan, S.I.
• Enzymatic synthesis of butyl acetate in a packed bed reactor underliquid and supercritical conditions

  Escandell, J.; Wurm, D.J.; Belleville, M.-P.; Sanchez, J.; Harasek, M.; Paolucci-Jeanjean, D.
• Engineered alkane-hydroxylating cytochrome P450(BM3) exhibiting nativelike catalytic properties
• Direct catalytic-oxidation of methane to methanol—a review
• Production of α,(-Alkanediols using Escherichia coli expressing a cytochrome p450 from Acinetobacter sp. OC4

  Fujii, T.; Narikawa, T.; Sumisa, F.; Arisawa, A.; Takeda, K.; Kato, J.
• Application of a continuously stirred tank bioreactor (CSTR) for bioremediation of hydrocarbon-rich industrial wastewater effluents

  Gargouri, B.; Karray, F.; Mhiri, N.; Aloui, F.; Sayadi, S.
• Biological conversion of methane to liquid fuels: status and opportunities
• Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase
• Catalyst-controlled aliphatic C–H oxidations with a predictive model for site-selectivity
• Whole-cell bio-oxidation of n-dodecane using the alkane hydroxylase system of P-putida GPo1 expressed in E-coil
• Substrate-specificity of soluble methane monooxygenase − mechanistic implications
• Selective oxidation of methane by the bis(mu-oxo) dicopper core stabilized on ZSM-5 and mordenite zeolites

  Groothaert, M.H.; Smeets, P.J.; Sels, B.F.; Jacobs, P.A.; Schoonheydt, R.A.
• Engineered catalytic biofilms for continuous large scale production of n-octanol and ( S )-styrene oxide
• Single-site trinuclear copper oxygen clusters in mordenite for selective conversion of methane to methanol

  Grundner, S.; Markovits, M.A.C.; Li, G.; Tromp, M.; Pidko, E.A.; Hensen, E.J.M.; Jentys, A.; Sanchez-Sanchez, M.; Lercher, J.A.
• Hanson, R.S.; Hanson, T.E.
• Methane partial oxidation to methanol over Ga2O3 based catalysts: use of the CH4 /D2 exchange reaction as a design tool

  Hargreaves, J.S.J.; Hutchings, G.J.; Joyner, R.W.; Taylor, S.H.
• Non-enzymatic regeneration of nicotinamide and flavin cofactors for monooxygenase catalysis
• Separation of methanol from methanol/water mixtures with pervaporation hybrid membranes
• A review of separation technologies in current and future biorefineries

  Huang, H.J.; Ramaswamy, S.; Tschirner, U.W.; Ramarao, B.V.
• Strategies for regeneration of nicotinamide coenzymes emphasizing self-sufficient closed-loop recycling systems
• Biocatalytic conversion of methane to methanol as a key step for development of methane-Based biorefineries

  Hwang, I.Y.; Lee, S.H.; Choi, Y.S.; Park, S.J.; Na, J.G.; Chang, I.S.; Kim, C.; Kim, H.C.; Kim, Y.H.; Lee, J.W.; Lee, E.Y.
• Methane oxidation at 55 degrees C and pH 2 by a thermoacidophilic bacterium belonging to the Verrucomicrobia phylum

  Islam, T.; Jensen, S.; Reigstad, L.J.; Larsen, O.; Birkeland, N.K.
• Methane hydroxylation using light energy by the combination of thylakoid and methane monooxygenase

  Ito, H.; Mori, F.; Tabata, K.; Okura, I.; Kamachi, T.
• Activation of the hydroxylase of sMMO from Methylococcus-capsulatus (Bath) by hydrogen-peroxide
• Selective oxidation of methane to methanol catalyzed, with CH activation, by homogeneous, cationic gold

  Jones, C.J.; Taube, D.; Ziatdinov, V.R.; Periana, R.A.; Nielsen, R.J.; Oxgaard, J.; Goddard, W.A.
• Enzyme Catalysis in an Aqueous/Organic Segment Flow Microreactor: Ways to Stabilize Enzyme Activity
• Use of perfluorocarboxylic acids to trick cytochrome p450bm3 into initiating the hydroxylation of gaseous alkanes
• Direct hydroxylation of primary carbons in small alkanes by wild-type cytochrome P450 BM3 containing perfluorocarboxylic acids as decoy molecules
• Selective oxidation of methane by molecular oxygen catalyzed by a bridged binuclear ruthenium complex at moderate pressures and ambient temperature
• Kim, J.; Grate, J.W.; Wang, P.
• Regeneration of the nicotinamide cofactor using a mediator-free electrochemical method with a tin oxide electrode
• Optimization of lab scale methanol production by Methylosinus trichosporium OB3b
• Partial oxidation of methane over silica catalysts promoted by 3D transition-metal ions

  Kobayashi, T.; Nakagawa, K.; Tabata, K.; Haruta, M.
• In vivo evolution of butane oxidation by terminal alkane hydroxylases AlkB and CYP153A6

  Koch, D.J.; Chen, M.M.; van Beilen, J.B.; Arnold, F.H.
• Pervaporative removal of organics from water using hydrophobic membranes Binary mixtures
• Novel dual extraction process for acetone-butanol-ethanol fermentation
• Petroleum-contaminated water treatment in a fluidized-bed bioreactor with immobilized Rhodococcus cells

  Kuyukina, M.S.; Ivshina, I.B.; Serebrennikova, M.K.; Krivorutchko, A.B.; Podorozhko, E.A.; Ivanov, R.V.; Lozinsky, V.I.
• Catalytic oxygenation of organic substrates: toward greener ways for incorporating oxygen
• H 2 -driven cofactor regeneration with NAD(P)+-reducing hydrogenases
• Efficient and selective formation of methanol from methane in a fuel cell-type reactor
• Coenzyme analogs: excellent substitutes (not poor imitations) for electrochemical regeneration
• Selective oxidation of methane and its homologues to alcohols catalyzed by gold compounds and a proposed reaction mechanism

  Levchenko, L.A.; Lobanova, N.G.; Martynenko, V.M.; Sadkov, A.P.; Shestakov, A.F.; Shilova, A.K.; Shilov, A.E.
• Biological methane oxidation: Regulation, biochemistry, and active site structure of particulate methane monooxygenase
• Rhodococcus erythropolis strain NTU-1 efficiently degrades and traps diesel and crude oil in batch and fed-batch bioreactors
• Towards continuous sustainable processes for enzymatic synthesis of biodiesel in hydrophobic ionic liquids/supercritical carbon dioxide biphasic systems
• Halogenated metalloporphorin complexes as catalysts for selective reactions of acyclic alkanes with molecular oxygen
• Integrated two-liquid phase bioconversion and product-recovery processes for the oxidation of alkanes: process design and economic evaluation
• Microbial communities involved in anaerobic degradation of alkanes

  Mbadinga, S.M.; Wang, L.Y.; Zhou, L.; Liu, J.F.; Gu, J.D.; Mu, B.Z.
• Methanol biosynthesis by covalently immobilized cells of Methylosinus trichosporium : batch and continuous studies
• Direct conversion of ethane to ethanol by engineered cytochrome P450BM3

  Meinhold, P.; Peters, M.W.; Chen, M.M.Y.; Takahashi, K.; Arnold, F.H.
• Hydrogen peroxide as an effecter on the inactivation of particulate methane monooxygenase under aerobic conditions

  Miyaji, A.; Suzuki, M.; Baba, T.; Kamachi, T.; Okura, I.
• The P450 Superfamily: Updated Listing of All Genes and Recommended Nomenclature for the chromosomal Loci

  Nebert, D.W.; Nelson, D.R.; Adesnik, M.; Coon, M.J.; Estabrook, R.W.; Gonzalez, F.J.; Guengerich, F.P.; Gunsalus, I.C.; Johnson, E.F.; Kemper, B.; Levin, W.; Phillips, I.R.; Sato, R.; Waterman, M.R.
• The P450 superfamily: update on new sequences, gene-mapping, and recommended nomenclature

  Nebert, D.W.; Nelson, D.R.; Coon, M.J.; Estabrook, R.W.; Feyereisen, R.; Fujiikuriyama, Y.; Gonzalez, F.J.; Guengerich, F.P.; Gunsalus, I.C.; Johnson, E.F.; Loper, J.C.; Sato, R.; Waterman, M.R.; Waxman, D.J.
• The P450 Superfamily: update on new sequences, gene-mapping, accession numbers, early trivial names of enzymes, and nomenclature

  Nelson, D.R.; Kamataki, T.; Waxman, D.J.; Guengerich, F.P.; Estabrook, R.W.; Feyereisen, R.; Gonzalez, F.J.; Coon, M.J.; Gunsalus, I.C.; Gotoh, O.; Okuda, K.; Nebert, D.W.
• P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature

  Nelson, D.R.; Koymans, L.; Kamataki, T.; Stegeman, J.J.; Feyereisen, R.; Waxman, D.J.; Waterman, M.R.; Gotoh, O.; Coon, M.J.; Estabrook, R.W.; Gunsalus, I.C.; Nebert, D.W.
• Biodegradation pattern of hydrocarbons from a fuel oil-type complex residue by an emulsifier-producing microbial consortium

  Nievas, M.L.; Commendatore, M.G.; Esteves, J.L.; Bucala, V.
• Functional expression system for cytochrome P450 genes using the reductase domain of self-sufficient P450RhF from Rhodococcus sp NCIMB 9784
• Regio- and stereoselective subterminal hydroxylations of n-Decane by fungi in a liquid-Liquid interface bioreactor (L–L IBR)
• Enhancement of biodegradation of oil adsorbed on fine soils in a bioslurry reactor

  Okuda, T.; Alcantara-Garduno, M.E.; Suzuki, M.; Matsui, C.; Kose, T.; Nishijima, W.; Okada, M.
• Park, D.H.; Lee, J.
• Microbial oxidation of hydrocarbons: properties of a soluble methane monooxygenase from a facultative methane-utilizing organism, Methylobacterium sp. Strain CRL-26
• Butane oxidation process development in a circulating fluidized bed
• A mercury-catalyzed, high-yield system for the oxidation of methane to methanol

  Periana, R.A.; Taube, D.J.; Evitt, E.R.; Loffler, D.G.; Wentrcek, P.R.; Voss, G.; Masuda, T.
• Evolving P450pyr hydroxylase for highly enantioselective hydroxylation at non-activated carbon atom

  Pham, S.Q.; Pompidor, G.; Liu, J.; Li, X.D.; Li, Z.
• Engineering of recombinant E. coli cells co-expressing P450pyrTM monooxygenase and glucose dehydrogenase for highly regio- and stereoselective hydroxylation of alicycles with cofactor recycling
• Identification of novel methane-, ethane-, and propane-oxidizing bacteria at marine hydrocarbon seeps by stable isotope probing
• Analysis of methane biodegradation by Methylosinus trichosporium OB3b
• Selective catalytic oxidation of CH bonds with molecular oxygen

  Roduner, E.; Kaim, W.; Sarkar, B.; Urlacher, V.B.; Pleiss, J.; Glaser, R.; Einicke, W.D.; Sprenger, G.A.; Beifuß, U.; Klemm, E.; Liebner, C.; Hieronymus, H.; Hsu, S.F.; Plietker, B.; Laschat, S.
• Synthesis, molecular structure, and catalytic potential of the tetrairon complex Fe 4 (N 3 O 2 -L)( 4 )(μ-O)( 2 ) ( 4+ ) (L=1-carboxymethyl-4,7-dimethyl-1,4,7-triazacyclononane)

  Romakh, V.B.; Therrien, B.; Suss-Fink, G.; Shul'pin, G.B.
• P450cam biocatalysis in surfactant-stabilized two-phase emulsions
• Regioselective -hydroxylation of medium-chain n-alkanes and primary alcohols by CYP153 enzymes from Mycobacterium marinum and Polaromonas sp strain JS666

  Scheps, D.; Malca, S.H.; Hoffmann, H.; Nestl, B.M.; Hauer, B.
• Whole-cell biocatalysis for selective and productive CO functional group introduction and modification

  Schrewe, M.; Julsing, M.K.; Buhler, B.; Schmid, A.
• Semrau, J.D.; Dispirito, A.A.; Yoon, S.
• Mossbauer studies of alkane omega-hydroxylase: evidence for a diiron cluster in an integral-membrane enzyme

  Shanklin, J.; Achim, C.; Schmidt, H.; Fox, B.G.; Munck, E.
• Distribution and diversity of Verrucomicrobia methanotrophs in geothermal and acidic environments

  Sharp, C.E.; Smirnova, A.V.; Graham, J.M.; Stott, M.B.; Khadka, R.; Moore, T.R.; Grasby, S.E.; Strack, M.; Dunfield, P.F.
• Anaerobic oxidation of methane and its homologues in the presence of gold compounds

  Shestakov, A.F.; Shilova, A.K.; Sadkov, A.P.; Lariontseva, N.V.; Golovanova, S.A.; Levchenko, L.A.; Shilov, A.E.
• Direct conversion of methane to methanol and formaldehyde over a double-layered catalyst bed in the presence of steam

  Shi, C.L.; Sun, Q.; Hu, H.C.; Herman, R.G.; Klier, K.; Wachs, I.E.
• Recent progress in oxidation of n-alkanes by heterogeneous catalysis

  Sivaramakrishna, A.; Suman, P.; Goud, E.V.; Janardan, S.; Sravani, C.; Yadav, C.S.; Clayton, H.S.
• Smith, T.J.; Murrell, J.C.
• Oxidation of methane and ethylene in water at ambient conditions

  Sorokin, A.B.; Kudrik, E.V.; Alvarez, L.X.; Afanasiev, P.; Millet, J.M.M.; Bouchu, D.
• Electrochemical reduction of CO 2 catalysed by Geobacter sulfurreducens grown on polarized stainless steel cathodes

  Soussan, L.; Riess, J.; Erable, B.; Delia, M.L.; Bergel, A.
• Biocatalytic hydroxylation of n-butane with in situ cofactor regeneration at low temperature and under normal pressure

  Staudt, S.; Mueller, C.A.; Marienhagen, J.; Boeing, C.; Buchholz, S.; Schwaneberg, U.; Groeger, H.
• Biocatalytic methanol production from methane with Methylosinus trichosporium OB3b: an approach to improve methanol accumulation
• CYP63A2, a catalytically versatile fungal P450 monooxygenase capable of oxidizing higher-molecular-weight polycyclic aromatic hydrocarbons, alkylphenols, and alkanes

  Syed, K.; Porollo, A.; Lam, Y.W.; Grimmett, P.E.; Yadav, J.S.
• Hydrogen and methanol formation utilizing bioprocesses
• The partial oxidation of methane to methanol: an approach to catalyst design

  Taylor, S.H.; Hargreaves, J.S.J.; Hutchings, G.J.; Joyner, R.W.; Lembacher, C.W.
• Dioxygen activation in soluble methane monooxygenase
• First structural-functional model of methane monooxygenase

  Trukhan, V.M.; Polukhov, V.V.; Sulimenkov, I.V.; Ovanesyan, N.S.; Koval'chuk, N.A.; Dodonov, A.F.; Shteinman, A.A.
• Cofactor regeneration—an important aspect of biocatalysis
• Production of 1-Octanol from n-Octane by Pseudomonas putida KT2440

  Vallon, T.; Glemser, M.; Malca, S.H.; Scheps, D.; Schmid, J.; Siemann-Herzberg, M.; Hauer, B.; Takors, R.
• Effect of membrane and process characteristics on cost and energy usage for separating alcohol-water mixtures using a hybrid vapor stripping-vapor permeation process
• A review of pervaporation for product recovery from biomass fermentation processes
• Partial oxidation of methane to methanol − Comparison of heterogeneous catalyst and homogeneous gas-phase reactions
• Partial oxidation of methane on Mo/Sn/P silica supported catalysts
• Enrichment, Isolation and some properties of methane-utilizing bacteria
• Production of methanol from methane by methanotrophic bacteria

  Xin, J.Y.; Cui, J.R.; Niu, J.Z.; Hua, S.F.; Xia, C.G.; Li, S.B.; Zhu, L.M.
• Engineering of P450pyr hydroxylase for the highly regio- and enantioselective subterminal hydroxylation of alkanes
• First steps towards a Zn/Co(III) sep-driven P450 BM3 reactor
• Expanding the alkane oxygenase toolbox: new enzymes and applications
• Alkane hydroxylases involved in microbial alkane degradation
• Substrate specificity of the alkane hydroxylase system of Pseudomonas oleovorans GPo1
• Zilly, F.E.; Acevedo, J.P.; Augustyniak, W.; Deege, A.; Haeusig, U.W.; Reetz, M.T.