Biocatalysts for selective introduction of oxygen

Three types of oxygenase biocatalysts are treated in detail in this review: the non-haem iron alkene mono-oxygenases, the haem and vanadium haloperoxidases, and flavin-based Baeyer–Villiger mono-oxygenases. Other oxygenases are briefly included for comparison. Characteristics of the biocatalysts are presented, and the scope and limitations concerning their applicability for the selective introduction of oxygen are discussed. Key issues include catalytic activity, productivity, cloning and expression, as well as process engineering aspects. Various bottlenecks are identified for the different biocatalysts and measures to increase the number of oxygenase reactions in practical use are discussed.

[1]  Andrea Mattevi,et al.  Crystal structure of a Baeyer-Villiger monooxygenase. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[2]  R. Sheldon,et al.  Selective oxidations catalyzed by peroxidases , 1997 .

[3]  J. Bont,et al.  Bioformation of optically pure epoxides , 1993 .

[4]  H. Heipieper,et al.  Prediction of the Adaptability of Pseudomonas putida DOT-T1E to a Second Phase of a Solvent for Economically Sound Two-Phase Biotransformations , 2005, Applied and Environmental Microbiology.

[5]  L. Hager,et al.  Post-translational modifications of chloroperoxidase from Caldariomyces fumago. , 1987, Archives of biochemistry and biophysics.

[6]  Ortiz de Montellano,et al.  Cytochrome P-450: Structure, Mechanism, and Biochemistry , 1986 .

[7]  H. Dalton,et al.  The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate n-alkanes, n-alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds. , 1977, The Biochemical journal.

[8]  A. Willetts Structural studies and synthetic applications of Baeyer-Villiger monooxygenases. , 1997, Trends in biotechnology.

[9]  D. Leak,et al.  Cloning, Expression, and Site-Directed Mutagenesis of the Propene Monooxygenase Genes from Mycobacterium sp. Strain M156 , 2005, Applied and Environmental Microbiology.

[10]  Stephen J. Lippard,et al.  Crystal structure of a bacterial non-haem iron hydroxylase that catalyses the biological oxidation of methane , 1993, Nature.

[11]  M. Mihovilovic,et al.  Asymmetric oxidations at sulfur catalyzed by engineered strains that overexpress cyclohexanone monooxygenase , 1999 .

[12]  M. Manns,et al.  Heterologous expression of human drug-metabolizing enzymes. , 1997, Drug metabolism and disposition: the biological fate of chemicals.

[13]  Djamaladdin G. Musaev,et al.  Mechanism of the methane → methanol conversion reaction catalyzed by methane monooxygenase: A density functional study , 1999 .

[14]  Stephen J. Lippard,et al.  Mechanistic studies of the reaction of reduced methane monooxygenase hydroxylase with dioxygen and substrates , 1999 .

[15]  John C Whitman,et al.  Improving catalytic function by ProSAR-driven enzyme evolution , 2007, Nature Biotechnology.

[16]  S. Lütz,et al.  Electroenzymatic Synthesis of Chiral Sulfoxides , 2006 .

[17]  V. Alphand,et al.  Microbial transformations 59: first kilogram scale asymmetric microbial Baeyer-Villiger oxidation with optimized productivity using a resin-based in situ SFPR strategy. , 2005, Biotechnology and bioengineering.

[18]  D. Leak,et al.  Cloning and expression of the genes encoding the propene monooxygenase from Xanthobacter, Py2 , 2004, Applied Microbiology and Biotechnology.

[19]  John M Woodley,et al.  Microbial biocatalytic processes and their development. , 2006, Advances in applied microbiology.

[20]  W. Pryor Cytochrome P450: Structure, mechanism, and biochemistry , 1996 .

[21]  U. Kragl,et al.  Synthesis of chiral ε-lactones in a two-enzyme system of cyclohexanone mono-oxygenase and formate dehydrogenase with integrated bubble-free aeration , 1997 .

[22]  J. Woodley,et al.  Large scale production of cyclohexanone monooxygenase from Escherichia coli TOP10 pQR239. , 2001, Enzyme and microbial technology.

[23]  E. Horjales,et al.  Cross-linked crystals of chloroperoxidase. , 2002, Biochemical and biophysical research communications.

[24]  J. Stewart,et al.  An Efficient Enzymatic Baeyer–Villiger Oxidation by Engineered Escherichiacoli Cells under Non‐Growing Conditions , 2002, Biotechnology progress.

[25]  H. Lipson Crystal Structures , 1949, Nature.

[26]  V. Alphand,et al.  Microbiological transformations. Part 51: The first example of a dynamic kinetic resolution process applied to a microbiological Baeyer–Villiger oxidation , 2002 .

[27]  D. Leak,et al.  The alkene monooxygenase from Xanthobacter Py2 is a binuclear non‐haem iron protein closely related to toluene 4‐monooxygenase , 1998, FEBS letters.

[28]  A. A. Shteinman,et al.  The mechanism of methane and dioxygen activation in the catalytic cycle of methane monooxygenase , 1995, FEBS letters.

[29]  M G Wubbolts,et al.  Production of enantiopure styrene oxide by recombinant Escherichia coli synthesizing a two-component styrene monooxygenase. , 2000, Biotechnology and bioengineering.

[30]  Motoshi Suzuki,et al.  The Biotransformation of Propylene to Propylene Oxide by Methylococcus Capsulatus (Bath): 2. A Study of the Biocatalyst Stability , 1992 .

[31]  H. Dalton,et al.  Activation of the hydroxylase of sMMO from Methylococcus capsulatus (Bath) by hydrogen peroxide. , 1993, Biochimica et biophysica acta.

[32]  V Massey,et al.  Mechanistic studies of cyclohexanone monooxygenase: chemical properties of intermediates involved in catalysis. , 2001, Biochemistry.

[33]  John M. Woodley,et al.  Characterization of a recombinant Escherichia coli TOP10 [pQR239] whole-cell biocatalyst for stereoselective Baeyer–Villiger oxidations , 2003 .

[34]  Andrew L. Feig,et al.  Reactions of Non-Heme Iron(II) Centers with Dioxygen in Biology and Chemistry , 1994 .

[35]  P. Trudgill,et al.  The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871. , 1976, European journal of biochemistry.

[36]  L. Kanerva,et al.  Chloroperoxidase-catalysed oxidation of alcohols to aldehydes , 2000 .

[37]  C. Murphy New frontiers in biological halogenation. , 2003, Journal of applied microbiology.

[38]  J. Andreesen,et al.  Cloning and characterization of a gene cluster involved in tetrahydrofuran degradation in Pseudonocardia sp. strain K1 , 2003, Archives of Microbiology.

[39]  N. Gorlatova,et al.  Purification, characterization, and mechanism of a flavin mononucleotide-dependent 2-nitropropane dioxygenase from Neurospora crassa. , 1998, Applied and environmental microbiology.

[40]  Stephen J. Lippard,et al.  Structure and Mössbauer Spectrum of a (μ-1,2-Peroxo)bis(μ-carboxylato)diiron(III) Model for the Peroxo Intermediate in the Methane Monooxygenase Hydroxylase Reaction Cycle , 1996 .

[41]  K. Yoshizawa Two-step concerted mechanism for methane hydroxylation on the diiron active site of soluble methane monooxygenase. , 2000, Journal of inorganic biochemistry.

[42]  T. Lee,et al.  Peroxide oxidation of primary alcohols to aldehydes by chloroperoxidase catalysis. , 1983, Biochemical and biophysical research communications.

[43]  D. Leak,et al.  The microbial production of epoxides , 1992 .

[44]  A. Choi,et al.  Cationic Species Can Be Produced in Soluble Methane Monooxygenase-Catalyzed Hydroxylation Reactions; Radical Intermediates Are Not Formed , 1999 .

[45]  a Takaharu Ookubo,et al.  cis-μ-1,2-Peroxo Diiron Complex: Structure and Reversible Oxygenation , 1996 .

[46]  R. Sheldon,et al.  Highly efficient immobilization of glycosylated enzymes into polyurethane foams. , 2000, Biotechnology and Bioengineering.

[47]  V. Alphand,et al.  Microbial Transformations, 56. Preparative Scale Asymmetric Baeyer–Villiger Oxidation using a Highly Productive “Two‐in‐One” Resin‐Based in situ SFPR Concept , 2004 .

[48]  B. Fox,et al.  Recombinant toluene-4-monooxygenase: catalytic and Mössbauer studies of the purified diiron and rieske components of a four-protein complex. , 1996, Biochemistry.

[49]  S. Colonna,et al.  Oxidation of organic cyclic sulfites to sulfates: a new reaction catalyzed by cyclohexanone monooxygenase , 1998 .

[50]  B. Robertson,et al.  Stereoselective synthesis of S-(-)-B-blockers via microbially produced epoxide intermediates , 1987 .

[51]  John M Woodley,et al.  On oxygen limitation in a whole cell biocatalytic Baeyer–Villiger oxidation process , 2006, Biotechnology and bioengineering.

[52]  R. H. Olsen,et al.  Nucleotide sequence analysis of genes encoding a toluene/benzene-2-monooxygenase from Pseudomonas sp. strain JS150 , 1995, Applied and environmental microbiology.

[53]  T. Smith,et al.  Adventitious reactions of alkene monooxygenase reveal common reaction pathways and component interactions among bacterial hydrocarbon oxygenases , 2005, The FEBS journal.

[54]  R. Sheldon,et al.  Improvement of the total turnover number and space-time yield for chloroperoxidase catalyzed oxidation. , 1997, Biotechnology and bioengineering.

[55]  J. Lipscomb,et al.  Transient intermediates of the methane monooxygenase catalytic cycle. , 1993, The Journal of biological chemistry.

[56]  J. Stewart,et al.  ‘Designer yeast’: a new reagent for enantioselective Baeyer–Villiger oxidations , 1996 .

[57]  R. Germani,et al.  Stabilization of Chloroperoxidase by Polyethylene Glycols in Aqueous Media: Kinetic Studies and Synthetic Applications , 2008, Biotechnology progress.

[58]  O. Weichold,et al.  Biotransformations with peroxidases. , 1999, Advances in biochemical engineering/biotechnology.

[59]  V. Alphand,et al.  Comparison of microbiologically and enzymatically mediated Baeyer–Villiger oxidations: synthesis of optically active caprolactones , 1996 .

[60]  Thomas E Hanson,et al.  Methanotrophic bacteria. , 1996, Microbiological reviews.

[61]  D. Bianchi,et al.  Cyclohexanone monooxygenase catalyzed oxidation of methyl phenyl sulfide and cyclohexanone with macromolecular NADP in a membrane reactor , 1993, Biotechnology Letters.

[62]  M. Mahmoudian,et al.  Biocatalysts for production of chiral epoxides , 1992, Applied Microbiology and Biotechnology.

[63]  D. Clark,et al.  New reaction system for hydrocarbon oxidation by chloroperoxidase. , 2006, Biotechnology and bioengineering.

[64]  Roger A. Sheldon,et al.  Enzyme Immobilization: The Quest for Optimum Performance , 2007 .

[65]  J. Shennan Utilisation of C2–C4 gaseous hydrocarbons and isoprene by microorganisms , 2006 .

[66]  L. Kanerva,et al.  Novel applications of chloroperoxidase: enantioselective oxidation of racemic epoxyalcohols , 1999 .

[67]  P. Barbieri,et al.  Analysis of the Gene Cluster Encoding Toluene/o-Xylene Monooxygenase from Pseudomonas stutzeri OX1 , 1998, Applied and Environmental Microbiology.

[68]  B. Fox,et al.  Toluene Monooxygenase-Catalyzed Epoxidation of Alkenes , 2000, Applied and Environmental Microbiology.

[69]  I. Schlichting,et al.  Crystal Structures of Chloroperoxidase with Its Bound Substrates and Complexed with Formate, Acetate, and Nitrate* , 2006, Journal of Biological Chemistry.

[70]  Frances H. Arnold,et al.  Laboratory evolution of a soluble, self-sufficient, highly active alkane hydroxylase , 2002, Nature Biotechnology.

[71]  M. Mihovilovic,et al.  An Enantiodivergent Trend in Microbial Baeyer−Villiger Oxidations of Functionalized Pentalenones by Recombinant Whole Cells Expressing Monooxygenases from Acinetobacter and Pseudomonas , 2003 .

[72]  J D Lipscomb,et al.  Large kinetic isotope effects in methane oxidation catalyzed by methane monooxygenase: evidence for C-H bond cleavage in a reaction cycle intermediate. , 1996, Biochemistry.

[73]  S. Colonna,et al.  Recent biotechnological developments in the use of peroxidases. , 1999, Trends in biotechnology.

[74]  D. Clark,et al.  Deactivation mechanisms of chloroperoxidase during biotransformations , 2006, Biotechnology and bioengineering.

[75]  Hiroki Iida,et al.  An aerobic, organocatalytic, and chemoselective method for Baeyer-Villiger oxidation. , 2005, Angewandte Chemie.

[76]  S. Murahashi,et al.  Flavin-catalyzed oxidation of amines and sulfur compounds with hydrogen peroxide , 1989 .

[77]  R. Sheldon,et al.  Chloroperoxidase-catalyzed enantioselective oxidations in hydrophobic organic media. , 2001, Biotechnology and bioengineering.

[78]  Thomas K. Wood,et al.  Directed Evolution of Toluene ortho-Monooxygenase for Enhanced 1-Naphthol Synthesis and Chlorinated Ethene Degradation , 2002, Journal of bacteriology.

[79]  A. Baeyer,et al.  Einwirkung des Caro'schen Reagens auf Ketone , 1899 .

[80]  M. Baboulene,,et al.  Regioselective bromohydroxylation of alkenes catalyzed by chloroperoxidase: Advantages of the immobilization of enzyme on talc , 1998 .

[81]  J. Dordick,et al.  Highly enantioselective oxidation of cis-cyclopropylmethanols to corresponding aldehydes catalyzed by chloroperoxidase. , 2002, The Journal of organic chemistry.

[82]  A. Conesa,et al.  Examining the Role of Glutamic Acid 183 in Chloroperoxidase Catalysis* , 2003, The Journal of Biological Chemistry.

[83]  D. Leak,et al.  Copper stress underlies the fundamental change in intracellular location of methane mono-oxygenase in methane-oxidizing organisms: Studies in batch and continuous cultures , 2004, Biotechnology Letters.

[84]  R. H. Olsen,et al.  Sequence analysis of the gene cluster encoding toluene-3-monooxygenase from Pseudomonas pickettii PKO1. , 1995, Gene.

[85]  B. Krebs,et al.  Methane monooxygenase and its related biomimetic models. , 2000, Current opinion in chemical biology.

[86]  R. Sheldon,et al.  Improving the catalytic performance of peroxidases in organic synthesis. , 2001, Trends in biotechnology.

[87]  R. Azerad Microbial models for drug metabolism. , 1999, Advances in biochemical engineering/biotechnology.

[88]  G J Lye,et al.  Application of in situ product-removal techniques to biocatalytic processes. , 1999, Trends in biotechnology.

[89]  S. Colonna,et al.  Enantioselective oxidation of sulfides to sulfoxides catalysed by bacterial cyclohexanone monooxygenases , 1996 .

[90]  A. Dexter,et al.  Highly Enantioselective Epoxidation of 1,1-Disubstituted Alkenes Catalyzed by Chloroperoxidase , 1995 .

[91]  D. Schomburg,et al.  Protocatechuate 3,4-dioxygenase , 1994 .

[92]  Jordan T. Watson,et al.  Catalytic activity of mesoporous silicate-immobilized chloroperoxidase , 2002 .

[93]  J. Woodley,et al.  Towards large-scale synthetic applications of Baeyer-Villiger monooxygenases. , 2003, Trends in biotechnology.

[94]  Karin Hofstetter,et al.  Integrated Biocatalytic Synthesis on Gram Scale: The Highly Enantioselective Preparation of Chiral Oxiranes with Styrene Monooxygenase , 2001 .

[95]  J. Lipscomb,et al.  Gating Effects of Component B on Oxygen Activation by the Methane Monooxygenase Hydroxylase Component (*) , 1995, The Journal of Biological Chemistry.

[96]  Roland Wohlgemuth,et al.  On the influence of oxygen and cell concentration in an SFPR whole cell biocatalytic Baeyer–Villiger oxidation process , 2006, Biotechnology and bioengineering.

[97]  J D Lipscomb,et al.  Crystal structure of the hydroxylase component of methane monooxygenase from Methylosinus trichosporium OB3b , 1997, Protein science : a publication of the Protein Society.

[98]  T. Uchida,et al.  Zr[bis(salicylidene)ethylenediaminato]-mediated Baeyer-Villiger oxidation: stereospecific synthesis of abnormal and normal lactones. , 2004, Proceedings of the National Academy of Sciences of the United States of America.

[99]  Stephen J. Lippard,et al.  Radical clock substrate probes and kinetic isotope effect studies of the hydroxylation of hydrocarbons by methane monooxygenase , 1993 .

[100]  K. Furuhashi Biological Routes to Optically Active Epoxides , 1993 .

[101]  A. Petri,et al.  Covalent immobilization of chloroperoxidase on silica gel and properties of the immobilized biocatalyst , 2004 .

[102]  J. Stewart,et al.  Understanding and Improving NADPH‐Dependent Reactions by Nongrowing Escherichia coli Cells , 2008, Biotechnology progress.

[103]  H. Dalton,et al.  The Biotransformation of Propylene to Propylene Oxide by Methylococcus Capsulatus (Bath): 1. Optimization of Rates , 1992 .

[104]  D. Dodds,et al.  Chloroperoxidase-catalyzed asymmetric oxidations: substrate specificity and mechanistic study. , 1995 .

[105]  D. Leak,et al.  The Alkene Monooxygenase from Xanthobacter Strain Py2 Is Closely Related to Aromatic Monooxygenases and Catalyzes Aromatic Monohydroxylation of Benzene, Toluene, and Phenol , 1999, Applied and Environmental Microbiology.

[106]  J. Murrell,et al.  Heterologous expression of alkene monooxygenase from Rhodococcus rhodochrous B-276. , 2001, European journal of biochemistry.

[107]  S. Raimondi,et al.  Comparison of cyclohexanone monooxygenase as an isolated enzyme and whole cell biocatalyst for the enantioselective oxidation of 1,3-dithiane , 2004 .

[108]  A. Munro,et al.  Roles of key active-site residues in flavocytochrome P450 BM3. , 1999, The Biochemical journal.

[109]  John M. Schwab,et al.  Cyclohexanone oxygenase: stereochemistry, enantioselectivity, and regioselectivity of an enzyme-catalyzed Baeyer-Villiger reaction , 1983 .

[110]  T. Poulos,et al.  Stereochemistry of the chloroperoxidase active site: crystallographic and molecular-modeling studies. , 1998, Chemistry & biology.

[111]  H. Hill,et al.  Cofactor-independent oxygenation reactions catalyzed by soluble methane monooxygenase at the surface of a modified gold electrode. , 2003, European journal of biochemistry.

[112]  M. Hofrichter,et al.  Heme-thiolate haloperoxidases: versatile biocatalysts with biotechnological and environmental significance , 2006, Applied Microbiology and Biotechnology.

[113]  D. Leak,et al.  Heterologous expression of alkene monooxygenase components from Xanthobacter autotrophicus Py2 and reconstitution of the active complex. , 2004, FEMS microbiology letters.

[114]  D. MacMillan,et al.  α-Oxidation Reactions , 2011 .

[115]  C. Sanfilippo,et al.  Chloroperoxidase from Caldariomyces fumago is active in the presence of an ionic liquid as co-solvent , 2004, Biotechnology Letters.

[116]  V. Urlacher,et al.  Catalytic Hydroxylation in Biphasic Systems using CYP102A1 Mutants , 2005 .

[117]  Peter W. H. Wan,et al.  Enzyme-catalysed Baeyer–Villiger oxidations , 1998 .

[118]  The crystal structure of chloroperoxidase: a heme peroxidase--cytochrome P450 functional hybrid. , 1995, Structure.

[119]  B. Witholt,et al.  Using proteins in their natural environment: potential and limitations of microbial whole-cell hydroxylations in applied biocatalysis. , 2001, Current opinion in biotechnology.

[120]  P. Adlercreutz,et al.  Use of celite-immobilised chloroperoxidase in predominantly organic media , 1999 .

[121]  A. Schmid,et al.  Process implementation aspects for biocatalytic hydrocarbon oxyfunctionalization. , 2004, Journal of biotechnology.

[122]  J. Trewhella,et al.  Global conformational changes control the reactivity of methane monooxygenase. , 1999, Biochemistry.

[123]  H. Wagenknecht,et al.  Identification of intermediates in the catalytic cycle of chloroperoxidase. , 1997, Chemistry & biology.

[124]  R. Sheldon,et al.  The Baeyer-Villiger reaction: new developments toward greener procedures. , 2004, Chemical reviews.

[125]  S. Ohk,et al.  Purification and properties of bacteriolytic enzymes from Bacillus licheniformis YS-1005 against Streptococcus mutans. , 1999, Bioscience, biotechnology, and biochemistry.

[126]  Karin Hofstetter,et al.  Coupling of biocatalytic asymmetric epoxidation with NADH regeneration in organic-aqueous emulsions. , 2004, Angewandte Chemie.

[127]  C. Chiappe,et al.  Application of hydrophilic ionic liquids as co-solvents in chloroperoxidase catalyzed oxidations , 2006 .

[128]  R. Sheldon,et al.  Chloroperoxidase catalyzed oxidations in t-butyl alcohol/water mixtures , 1997 .

[129]  S. Colonna,et al.  Microencapsulated chloroperoxidase as a recyclable catalyst for the enantioselective oxidation of sulfides with hydrogen peroxide. , 2004, Angewandte Chemie.

[130]  R. Sheldon,et al.  Selective oxidations with molecular oxygen, catalyzed by chloroperoxidase in the presence of a reductant , 1999 .

[131]  M. D. Corbett,et al.  Peroxide oxidation of indole to oxindole by chloroperoxidase catalysis. , 1979, The Biochemical journal.

[132]  S. Lippard,et al.  Geometry of the soluble methane monooxygenase catalytic diiron center in two oxidation states. , 1995, Chemistry & biology.

[133]  J D Lipscomb,et al.  Oxygen activation catalyzed by methane monooxygenase hydroxylase component: proton delivery during the O-O bond cleavage steps. , 1999, Biochemistry.

[134]  R. Sheldon,et al.  Selective oxygen transfer catalysed by heme peroxidases: synthetic and mechanistic aspects. , 2000, Current opinion in biotechnology.

[135]  R. Sheldon,et al.  Synthesis of substituted oxindoles by chloroperoxidase catalyzed oxidation of indoles , 1996 .

[136]  J. Tramper,et al.  Stereospecific formation of 1,2-epoxypropane, 1,2-epoxybutane and 1-chloro-2,3-epoxypropane by alkene-utilizing bacteria , 1985 .

[137]  G E Turfitt,et al.  The microbiological degradation of steroids: 4. Fission of the steroid molecule. , 1948, The Biochemical journal.

[138]  S. Colonna,et al.  Enantioselective synthesis of tert-butyl tert-butanethiosulfinate catalyzed by cyclohexanone monooxygenase. , 2001, Chirality.

[139]  Jon D. Stewart,et al.  Cyclohexanone Monooxygenase: A Useful Reagent for Asymmetric Baeyer-Villiger Reactions , 1998, Current Organic Chemistry.

[140]  S. Colonna,et al.  Use of isolated cyclohexanone monooxygenase from recombinant Escherichia coli as a biocatalyst for Baeyer-Villiger and sulfide oxidations. , 2002, Biotechnology and bioengineering.

[141]  Marco W. Fraaije,et al.  Baeyer-Villiger monooxygenases, an emerging family of flavin-dependent biocatalysts , 2003 .

[142]  J. Lipscomb,et al.  Dioxygen independent oxygenation of hydrocarbons by methane monooxygenae hydroxylase component , 1991 .

[143]  John M Woodley,et al.  Biocatalysis for pharmaceutical intermediates: the future is now. , 2007, Trends in biotechnology.

[144]  H. Saeki,et al.  Cloning and characterization of a Nocardia corallina B-276 gene cluster encoding alkene monooxygenase , 1994 .

[145]  J. Murrell,et al.  Improved System for Protein Engineering of the Hydroxylase Component of Soluble Methane Monooxygenase , 2002, Applied and Environmental Microbiology.

[146]  A. Schmid,et al.  Oxidative biotransformations using oxygenases. , 2002, Current opinion in chemical biology.

[147]  M. Hedström,et al.  A Mass Spectrometric Investigation of Native and Oxidatively Inactivated Chloroperoxidase , 2007, Chembiochem : a European journal of chemical biology.

[148]  N D Lourenço,et al.  Improved operational stability of peroxidases by coimmobilization with glucose oxidase. , 2000, Biotechnology and bioengineering.

[149]  Keith A. Powell,et al.  Directed Evolution and Biocatalysis. , 2001, Angewandte Chemie.

[150]  H. Dalton,et al.  Variations on a theme of Fe-O-Fe proteins. , 1994, Biochemical Society transactions.

[151]  S. Colonna,et al.  Chloroperoxidase and hydrogen peroxide: An efficient system for enzymatic enantioselective sulfoxidations. , 1992 .

[152]  D. Kelly,et al.  Flavin Monooxygenases—Uses as Catalysts for Baeyer‐Villiger Ring Expansion and Heteroatom Oxidation , 2001 .

[153]  S. Lippard,et al.  Crystal structures of the methane monooxygenase hydroxylase from Methylococcus capsulatus (Bath): Implications for substrate gating and component interactions , 1997, Proteins.

[154]  E. Torres,et al.  Stability and catalytic properties of chloroperoxidase immobilized on SBA-16 mesoporous materials , 2005 .

[155]  R. Libby,et al.  Quantitating Direct Chlorine Transfer from Enzyme to Substrate in Chloroperoxidase-catalyzed Reactions* , 1996, The Journal of Biological Chemistry.

[156]  R. Sheldon,et al.  Chloroperoxidase: Use of a Hydrogen Peroxide-Stat for Controlling Reactions and Improving Enzyme Performance , 1997 .

[157]  S. Colonna,et al.  A new enzymatic enantioselective synthesis of dialkyl sulfoxides catalysed by monooxygenases , 1997 .

[158]  J. Lipscomb,et al.  Probing the mechanism of C-H activation: oxidation of methylcubane by soluble methane monooxygenase from Methylosinus trichosporium OB3b. , 1999, Biochemistry.

[159]  J. Stewart,et al.  Recombinant Baker's Yeast as a Whole-Cell Catalyst for Asymmetric Baeyer−Villiger Oxidations , 1998 .

[160]  M. Taschner,et al.  The enzymatic Baeyer-Villiger oxidation: enantioselective synthesis of lactones from mesomeric cyclohexanones , 1988 .

[161]  F. Lakner,et al.  Enantioselective Epoxidation of ω-Bromo-2-methyl-1-alkenes Catalyzed by Chloroperoxidase. Effect of Chain Length on Selectivity and Efficiency , 1997 .

[162]  H. Leemhuis,et al.  Characterization of the Gene Cluster Involved in Isoprene Metabolism in Rhodococcus sp. Strain AD45 , 2000, Journal of bacteriology.

[163]  J. Lipscomb,et al.  Mechanistic insights into C-H activation from radical clock chemistry: oxidation of substituted methylcyclopropanes catalyzed by soluble methane monooxygenase from Methylosinus trichosporium OB3b. , 2000, Biochimica et biophysica acta.

[164]  B. Mueller,et al.  Monooxygenase-Mediated Baeyer—Villiger Oxidations , 2003 .

[165]  P. Rouvière,et al.  Assessing the substrate selectivities and enantioselectivities of eight novel Baeyer-Villiger monooxygenases toward alkyl-substituted cyclohexanones. , 2004, The Journal of organic chemistry.

[166]  R A Friesner,et al.  Activation of the C-H bond of methane by intermediate Q of methane monooxygenase: a theoretical study. , 2001, Journal of the American Chemical Society.

[167]  J. G. Leahy,et al.  Evolution of the soluble diiron monooxygenases. , 2003, FEMS microbiology reviews.

[168]  J. A. Thomas,et al.  Chloroperoxidase halogenation reactions. Chemical versus enzymic halogenating intermediates. , 1982, The Journal of biological chemistry.

[169]  R. Friesner,et al.  Intermediates in dioxygen activation by methane monooxygenase: a QM/MM study. , 2007, Journal of the American Chemical Society.

[170]  John M. Woodley,et al.  Process limitations in a whole-cell catalysed oxidation: Sensitivity analysis , 2006 .

[171]  Y. Imada,et al.  Asymmetric baeyer-villiger reaction with hydrogen peroxide catalyzed by a novel planar-chiral bisflavin. , 2002, Angewandte Chemie.

[172]  V. de Lorenzo,et al.  Engineering of a Stable Whole-Cell Biocatalyst Capable of (S)-Styrene Oxide Formation for Continuous Two-Liquid-Phase Applications , 1999, Applied and Environmental Microbiology.

[173]  E. Steckhan,et al.  First asymmetric electroenzymatic oxidation catalyzed by a peroxidase , 2004 .

[174]  R. Friesner,et al.  Dioxygen activation in methane monooxygenase: a theoretical study. , 2004, Journal of the American Chemical Society.

[175]  Giorgio Strukul,et al.  Transition Metal Catalysis in the Baeyer-Villiger Oxidation of Ketones. , 1998, Angewandte Chemie.

[176]  O. Hayaishi,et al.  Protocatechuate 3,4-Dioxygenase I. CRYSTALLIZATION AND CHARACTERIZATION , 1972 .

[177]  Christopher T. Walsh,et al.  Enzymic Baeyer–Villiger Oxidations by Flavin‐Dependent Monooxygenases , 1988 .

[178]  L. Hager,et al.  Biological Chlorination VI. CHLOROPEROXIDASE: A COMPONENT OF THE β-KETOADIPATE CHLORINASE SYSTEM , 1961 .

[179]  R. Sheldon,et al.  Chloroperoxidase-Catalyzed Oxidation of 5-Hydroxymethylfurfural , 1997 .

[180]  Andreas Schmid,et al.  Practical issues in the application of oxygenases. , 2003, Trends in biotechnology.

[181]  A. Butler Mechanistic considerations of the vanadium haloperoxidases , 1999 .

[182]  L. Hager,et al.  Highly Enantioselective Propargylic Hydroxylations Catalyzed by Chloroperoxidase. , 1999 .

[183]  J. Woodley,et al.  Choice of biocatalyst form for scalable processes. , 2006, Biochemical Society transactions.

[184]  R. Sheldon,et al.  Engineering chloroperoxidase for activity and stability , 2001 .

[185]  H. Dalton,et al.  Sequence-alignment modelling and molecular docking studies of the epoxygenase component of alkene monooxygenase from Nocardia corallina B-276. , 1998, European journal of biochemistry.

[186]  John M Woodley,et al.  Reactor Operation and Scale‐Up of Whole Cell Baeyer‐Villiger Catalyzed Lactone Synthesis , 2002, Biotechnology progress.

[187]  F. Arnold,et al.  A self-sufficient peroxide-driven hydroxylation biocatalyst. , 2003, Angewandte Chemie.

[188]  P. Ortiz de Montellano,et al.  Chloroperoxidase-catalyzed benzylic hydroxylation. , 1995, Archives of biochemistry and biophysics.

[189]  B. Fox,et al.  A Transient Intermediate of the Methane Monooxygenase Catalytic Cycle Containing an FeIVFeIV Cluster , 1993 .

[190]  Urs von Stockar,et al.  In situ product removal (ISPR) in whole cell biotechnology during the last twenty years. , 2003, Advances in biochemical engineering/biotechnology.