Modern Biooxidation Enzymes, Reactions and Applications

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ISBN: 9783527315079 | 3527315071
Cover: Hardcover
Copyright: 9/4/2007

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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.

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
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Modern Biooxidation Enzymes, Reactions and Applications

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