Modern Biooxidation Enzymes, Reactions and Applications
by Schmid, Rolf D.; Urlacher, VladaEdition: 1st
Format: Hardcover
Pub. Date: 2007-09-04
Publisher(s): Wiley-VCH
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Summary
Filling a gap in the literature, leading expert editors and top international authors present the field of biooxidation from an academic and industrial point of view, taking many examples from modern pharmaceutical research. Topics range from the application of different monooxygenases to applications in the pharmaceutical industry, making this volume of high interest not only for those working in biotechnology but also for organic synthetic chemists, among others.
Author Biography
Rolf Schmid obtained his PhD in 1970. After post-doctoral studies in France and the USA, he joined the research laboratories of Henkel KGaA in D?orf in 1972 where he became Director of the Biotechnology Laboratories. In 1987, he moved to the 'Gesellschaft f?technologische Forschung' (GBF) in Braunschweig where he headed the Division of Enzyme Technology and Natural Products Research.
In 1993, he accepted an invitation to build up the newly founded Institute for Technical Biochemistry at the University of Stuttgart. He is further in charge of the Department of Molecular Biotechnology at the Fraunhofer Institute for Membrane Science and Biotechnology in Stuttgart, and he is chairman of the IUPAC Commission of Biotechnology.
In 1993, he accepted an invitation to build up the newly founded Institute for Technical Biochemistry at the University of Stuttgart. He is further in charge of the Department of Molecular Biotechnology at the Fraunhofer Institute for Membrane Science and Biotechnology in Stuttgart, and he is chairman of the IUPAC Commission of Biotechnology.
Vlada B. Urlacher obtained her diploma in Biology at the University of Tashkent, Uzbekistan. After receiving her PhD from the Academy of Sciences, Uzbekistan, she spent a postdoctoral year at the Institute of Technical Biochemistry, University of Stuttgart, Germany and then two years in the Institute of Biotechnology, University Halle-Wittenberg, Germany. In 2001 she returned to the Institute of Technical Biochemistry, University of Stuttgart. Since 2003 she has been head of Biocatalysis group at this Insitute. Her main research interests are engineering the technical application of oxidizing enzymes.
Table of Contents
| Biooxidation with PQQ- and FAD-Dependent Dehydrogenases | p. 1 |
| Introduction | p. 1 |
| Basic Technical Information Regarding Membrane-bound Enzymes | p. 4 |
| Preparation of Cytosolic Fractions and Membrane Fractions | p. 4 |
| EDTA Treatment of the Membrane Fraction Carrying PQQ as Coenzyme | p. 9 |
| Assays of Enzyme Activity | p. 5 |
| PQQ-Dependent Dehydrogenases | p. 6 |
| Alcohol Oxidation | p. 6 |
| Membrane-Bound Alcohol Dehydrogenase (ADH III) | p. 6 |
| Soluble Alcohol Dehydrogenases | p. 9 |
| Cyclic Alcohol Dehydrogenase (Secondary Alcohol Dehydrogenase), Membrane-Bound | p. 9 |
| Glucose Oxidation | p. 11 |
| Membrane-Bound D-Glucose Dehydrogenase (m-GDH) | p. 11 |
| Soluble D-Glucose Dehydrogenase (s-GDH) | p. 12 |
| Applications of Quinoprotein GDHs as D-Glucose Sensors | p. 13 |
| Polyol Oxidation | p. 14 |
| D-Arabitol Dehydrogenase, Membrane-Bound | p. 14 |
| meso-Erythritol Oxidation Dehydrogenase, Membrane-Bound | p. 16 |
| D-Gluconate Oxidizing Polyol Dehydrogenase, Membrane-Bound | p. 17 |
| Glycerol Dehydrogenase, Membrane-Bound | p. 19 |
| D-Mannitol Dehydrogenase, Membrane-Bound | p. 20 |
| Ribitol Dehydrogenase, Membrane-Bound | p. 21 |
| D-Sorbitol Dehydrogenase, Membrane-Bound | p. 22 |
| L-Sorbosone Dehydrogenase, Membrane-Bound | p. 23 |
| Quinate Oxidation. Membrane-Bound Quinate Dehydrogenase (QDH) | p. 24 |
| FAD-Dependent Dehydrogenase | p. 27 |
| D-Fructose Dehydrogenase, Membrane-Bound | p. 27 |
| D-Gluconate Dehydrogenase, Membrane-Bound | p. 28 |
| D-Hexosamine Dehydrogenase, Membrane-Bound | p. 29 |
| 2-Keto-D-gluconate Dehydrogenase, Membrane-Bound | p. 31 |
| Sorbitol Dehydrogenase, Membrane-Bound | p. 32 |
| Miscellaneous | p. 33 |
| Aldehyde Dehydrogenase, Membrane-Bound | p. 33 |
| References | p. 35 |
| Catalytic Applications of Laccase | p. 43 |
| Properties of Classical Laccase | p. 43 |
| Structure | p. 43 |
| Enzymology | p. 44 |
| 4As Industrial Catalysts | p. 46 |
| Advantages | p. 46 |
| Shortcomings | p. 48 |
| Applications of Laccase for Industrial Oxidation Processes | p. 48 |
| Laboratory-Level Trials | p. 49 |
| Delignification | p. 49 |
| Dye and Colorant Bleaching | p. 50 |
| Bioremediation | p. 50 |
| Other Degradation Applications | p. 51 |
| Functional Biotransformation | p. 51 |
| Biosensing | p. 53 |
| Desirable Application Modes | p. 53 |
| Commercialized Applications | p. 55 |
| Preventing Taint in Cork Stoppers | p. 56 |
| Denim Bleaching | p. 56 |
| Paper Mill Effluent Treatment and Cardboard Strengthening | p. 56 |
| Major Hurdles to Further Development from Laboratory Trials | p. 57 |
| More Recent Developments | p. 57 |
| Novel Laccase Catalytic Systems | p. 57 |
| New Laccases | p. 57 |
| New Mediators | p. 60 |
| Cooperation with Other Enzymes | p. 62 |
| New Leads for Laccase Application | p. 62 |
| Laccase-Based Defense Against Biological and Chemical Warfare Agents | p. 62 |
| Degradation of PAH, Plastics, or Lipids | p. 63 |
| Enzymatic Fuel Cells/Batteries | p. 64 |
| Novel Synthetic Applications | p. 65 |
| Biorefinery | p. 66 |
| Further Developing Laccase Catalysis | p. 66 |
| Laccase Engineering | p. 66 |
| Laccase Production | p. 67 |
| References | p. 68 |
| Biocatalytic Scope of Baeyer-Villiger Monooxygenases | p. 77 |
| Introduction | p. 77 |
| The Baeyer-Villiger Reaction | p. 77 |
| Baeyer-Villiger Biocatalysts: Classification and Occurrence | p. 78 |
| Type I Baeyer-Villiger Monooxygenases | p. 78 |
| Type II Baeyer-Villiger Monooxygenases | p. 78 |
| Alternative Baeyer-Villiger Biocatalysts | p. 79 |
| Type I Baeyer-Villiger Monooxygenases: Versatile Oxidative Biocatalysts | p. 80 |
| Mechanistic and Structural Properties of Type I BVMOs | p. 80 |
| Diversity | p. 84 |
| Molecular Features | p. 86 |
| Kinetic Characteristics | p. 86 |
| Coenzyme Dependency | p. 87 |
| Uncoupling and Overoxidation | p. 88 |
| Biocatalyst Stability | p. 88 |
| Substrate Specificity | p. 89 |
| Unexplored Type I BVMOs | p. 90 |
| Mining Genomes for Novel BVMOs | p. 92 |
| Concluding Remarks | p. 93 |
| References | p. 94 |
| The Bacterial Cytochrome P450 Monooxygenases: P450cam and P450BM-3 | p. 99 |
| Introduction | p. 99 |
| Biotransformation by Bacterial P450 Enzymes | p. 99 |
| General Features of P450cam and P450BM-3 | p. 102 |
| Aromatic Compounds | p. 105 |
| Alkanes and Alicyclics | p. 109 |
| Terpenoid Compounds | p. 111 |
| Human Metabolites | p. 114 |
| The Scope of P450 Engineering | p. 116 |
| References | p. 117 |
| Cytochrome P450 Redox Partner Systems: Biodiversity and Biotechnological Implications | p. 123 |
| Introduction | p. 123 |
| P450 Redox Partners | p. 124 |
| A "Historical" Perspective | p. 124 |
| The P450 Catalytic Cycle and Electron Transfer Events | p. 125 |
| P450cam and its Reductase System | p. 127 |
| Adrenodoxin and Adrenodoxin Reductase | p. 128 |
| Cytochrome P450 Reductase | p. 129 |
| P450BM-3 and Related CPR Fusion Enzymes | p. 131 |
| A Novel Class of P450-Redox Partner Fusion Enzymes | p. 136 |
| Increasing P450-Redox Partner Complexity: Flavodoxins and Diverse Ferredoxins | p. 137 |
| Natural and Artificial P450-Redox Partner Fusion Enzymes and their Biocatalytic Potential | p. 138 |
| Other Routes to Driving P450 Catalytic Function | p. 140 |
| Uncoupling, Enzyme Stability and Coenzyme Issues | p. 142 |
| Future Prospects | p. 143 |
| References | p. 145 |
| Steroid Hydroxylation: Microbial Steroid Biotransformations Using Cytochrome P450 Enzymes | p. 155 |
| Introduction | p. 155 |
| Cytochrome P450-Dependent Steroid Hydroxylase Systems | p. 156 |
| Native Microorganisms in Steroid Biotransformation | p. 159 |
| 11[alpha]-Hydroxylation | p. 160 |
| 11[beta]-Hydroxylation | p. 161 |
| 16[alpha]-Hydroxylation | p. 162 |
| Conclusions | p. 163 |
| Genetically Modified Microorganisms in Steroid Biotransformation | p. 163 |
| Soluble Cytochromes P450 | p. 164 |
| Membrane-Bound Cytochromes P450 | p. 166 |
| Synopsis and Concluding Remarks | p. 170 |
| References | p. 171 |
| A Modular Approach to Biotransformation Using Microbial Cytochrome P450 Monooxygenases | p. 177 |
| Introduction | p. 177 |
| Experimental Outline | p. 180 |
| Gene Sequences | p. 180 |
| pT7NS-camAB | p. 180 |
| Plasmids to Express Bacterial CYPs | p. 180 |
| Preparation of Whole Cell Catalysts | p. 181 |
| Biotransformation of the CYP Substrates | p. 181 |
| Carbomycin A | p. 181 |
| Pravastatin | p. 182 |
| 7-Hydroxycoumarin | p. 182 |
| Biotransformation by CYP Reaction Array | p. 182 |
| Bacterial CYP Expression System in E. coli | p. 183 |
| Construction of a Bacterial CYP Library | p. 185 |
| Construction of a Bacterial CYP Reaction Array | p. 186 |
| Application of the CYP Reaction Array to Biotransformation Screening | p. 187 |
| References | p. 190 |
| Selective Microbial Oxidations in Industry: Oxidations of Alkanes, Fatty Acids, Heterocyclic Compounds, Aromatic Compounds and Glycerol Using Native or Recombinant Microorganisms | p. 193 |
| Introduction | p. 193 |
| Selective Oxidation of Hydrocarbons and Fatty Acids | p. 194 |
| Alkane Oxidation to Medium-Chain Alcohols [11] | p. 194 |
| Alkane and Fatty Acid Oxidation to Dicarboxylic Acids | p. 196 |
| Alkanes | p. 197 |
| Dicarboxylic Acids | p. 197 |
| Aromatic Compounds/Fine Chemicals | p. 198 |
| Conversion of Toxic Compounds: Catechols | p. 198 |
| Production of (R)-2-(4-Hydroxyphenoxy)propionic Acid | p. 199 |
| Selective Oxidation to Aromatic Aldehydes with Recombinant Cells | p. 200 |
| Styrene Oxide Production in a Two-Liquid Phase System | p. 200 |
| Heterocyclic Compounds | p. 200 |
| Enzymatic Oxidation of Methyl Groups in Aromatic Heterocycles | p. 201 |
| Preparation of 6-Hydroxynicotinic Acid | p. 202 |
| Preparation of 5-Hydroxypyrazinecarboxylic Acid | p. 202 |
| Preparation of 6-Hydroxy-(S)-nicotine and 4-[6-Hydroxypyridin-3-yl]4-oxobutyrate | p. 202 |
| Bulk Chemicals/Indigo | p. 203 |
| Glycerol Conversion to Dihydroxyacetone | p. 206 |
| Perspectives | p. 207 |
| References | p. 207 |
| Preparation of Drug Metabolites using Fungal and Bacterial Strains | p. 211 |
| Introduction | p. 211 |
| Phase I Drug-Metabolizing Enzymes | p. 212 |
| Needs and "Platforms" for the Generation of Drug Metabolites | p. 214 |
| Recombinant Human Cytochrome P450 (rhCYP) Systems (acquired from British Technology Group/University of Dundee) | p. 215 |
| Microbial Strains Performing Oxidative Reactions (in-house technology) | p. 215 |
| Microbial Models for Oxidative Drug Metabolism | p. 215 |
| 2Prokaryotic P450s | p. 218 |
| Microbial Eukaryotic P450s | p. 218 |
| Correlation of Microbial and Mammalian Oxidative Drug Metabolism | p. 221 |
| Correlation of Microbial Reactions with Human CYP Isozyme-Specific Reactions | p. 221 |
| Novartis Research Examples of Microbial Hydroxylations | p. 225 |
| Preparation of 10,11-Epoxy-carbamazepine and 10,11-Dihydro-10-hydroxy-carbamazepine | p. 225 |
| Preparation of 4-(4[prime]-Hydroxyanilino)-5-anilinophthalimide and 4,5-Bis-(4[prime]-hydroxyanilino)-phthalimide by Microbial Hydroxylation | p. 227 |
| Microbial Oxidation of Natural Products | p. 228 |
| Microbial Hydroxylation and Epoxidation of Milbemycins | p. 229 |
| Conclusions | p. 229 |
| References | p. 231 |
| Recombinant Yeast and Bacteria that Express Human P450s: Bioreactors for Drug Discovery, Development, and Biotechnology | p. 233 |
| Background | p. 234 |
| Importance of Recombinant P450s for Drug Development | p. 234 |
| Fundamentals of Heterologous Expression in Bacteria | p. 235 |
| Fundamentals of Heterologous Expression in Yeast | p. 236 |
| Comparison of P450 Levels and Enzymic Activities in Various Models | p. 237 |
| Use of E. coli P450 Expression Systems in Bioreactors | p. 240 |
| General Considerations | p. 240 |
| The Roche Experience | p. 240 |
| Background and Utility of P450 Systems in Pharma Research | p. 240 |
| Fermentation of Recombinant E. coli | p. 241 |
| Biotransformations Catalyzed by Recombinant CYP450 | p. 241 |
| Preparation of N-Desethyl Amodiaquine | p. 242 |
| The Novartis Experience | p. 244 |
| Introduction | p. 244 |
| Production of E. coli Cells with CYP Activity | p. 244 |
| Whole Cell Biotransformation | p. 246 |
| Recent Developments | p. 246 |
| Conclusion | p. 246 |
| References | p. 247 |
| Human Cytochrome P450 Monooxygenases - a General Model of Substrate Specificity and Regioselectivity | p. 253 |
| Introduction | p. 253 |
| What Can We Learn From Sequence? | p. 254 |
| The Cytochrome P450 Engineering Database (CYPED) | p. 254 |
| The Effect of Mutations on Activity | p. 255 |
| What Can We Learn from Structure? | p. 258 |
| 2The Role of Flexibility | p. 258 |
| The Role of Binding Site Shape | p. 259 |
| Conclusion | p. 261 |
| References | p. 262 |
| Approaches to Recycling and Substituting NAD(P)H as a CYP Cofactor | p. 265 |
| Introduction | p. 265 |
| Chemical Substitution of Cofactors | p. 266 |
| Enzymatic Regeneration of Cofactors | p. 267 |
| Photochemical Approaches to Substituting or Regenerating Cofactors for P450 Systems | p. 271 |
| Electrochemical Systems for Substitution or Regeneration of Cofactors | p. 272 |
| Electrochemical Regeneration of Natural Cofactors | p. 273 |
| Electrochemical Regeneration of Artificial Cofactors | p. 274 |
| Electrochemical Generation of Hydrogen Peroxide | p. 275 |
| Electrochemistry of P450 at Modified Electrodes | p. 275 |
| Electrochemistry of P450 in Surfactant Films | p. 276 |
| Incorporation of Cytochrome P450 in Conducting Polymers | p. 278 |
| Redox Mediators | p. 278 |
| Molecular Biological Approaches | p. 280 |
| Peroxide Shunt | p. 280 |
| Artificial Electron Transfer Systems | p. 281 |
| Changing the Cofactor Specificity of P450 Systems | p. 281 |
| Intracellular Cofactor Regeneration | p. 282 |
| Conclusion and Outlook | p. 282 |
| References | p. 284 |
| Index | p. 291 |
| Table of Contents provided by Ingram. All Rights Reserved. |
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