Biocatalysis for the pharmaceutical industry: discovery, development, and manufacturing
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Singapore [u.a.]
Wiley
2009
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Includes bibliographical references and index |
| Physical Description: | X, 324 S. Ill., graph. Darst. |
| ISBN: | 0470823143 9780470823149 |
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| adam_text | Titel: Biocatalysis for the pharmaceutical industry
Autor: Tao, Junhua
Jahr: 2009
Contents
Preface xi
1 Enzymes and Their Synthetic Applications: An Overview 1
1.1 Introduction 1
1.2 Enzyme Families 1
1.3 Enzyme Discovery and Optimization 2
1.4 Enzyme Production 3
1.5 Enzymes and Synthetic Applications 3
1.5.1 Ketoreductases (EC 1.1.1.2) 4
1.5.2 Enoate Reductases or Ene Reductases (EC 1.3.1.16) 4
1.5.3 Oxygenases (EC. xxxx) 5
1.5.4 Alcohol Oxidases (EC 1.1.3.X) 6
1.5.5 Peroxidases (EC l.ll.l.X) 7
1.5.6 Halogenases (EC. xxxx) 8
1.5.7 Nitrilases (EC 3.5.5.1) 9
1.5.8 Nitrile Hydratases (EC 4.2.1.84) 9
1.5.9 Epoxide Hydrolases (EC 3.3.2.X) 10
1.5.10 w-Transaminases (EC 2.6.1.X) 10
1.5.11 Hydroxynitrile Lyases (EC 4.1.2.X) 10
1.5.12 Aldolases (EC. xxxx) 12
1.5.13 Glycosidases (EC. xxxx) 12
1.5.14 Glycosyltransferase (EC. xxxx) 14
1.6 Conclusions 15
2 Expression Hosts for Enzyme Discovery and Production 21
2.1 Introduction 21
2.2 How to Choose an Expression System 22
2.3 Prokaryotic Expression Systems 24
2.3.1 Posttranslational Modification in Prokaryotes 25
2.3.2 Escherichia coli 25
2.3.3 Bacilli 26
2.3.4 Pseudomonas fluorescens 27
2.3.5 Other Prokaryotic Expression Systems 28
2.4 Eukaryotic Expression Systems 29
2.4.1 Yeasts 29
2.4.2 Filamentous Fungi 32
2.4.3 Insect/Baculovirus System 33
2.4.4 Mammalian Cell Cultures 34
2.4.5 Other Expression Systems 35
2.5 Cell-Free Expression Systems 36
2.6 Conclusions 37
3 Directed Enzyme Evolution and High-Throughput Screening 45
3.1 Introduction 45
3.2 Directed Evolution Library Creation Strategies 46
3.2.1 Random and Semi-Rational Mutagenesis 47
3.2.2 Gene Shuffling 48
3.3 Directed Evolution Library Screening/Selection Methods 52
3.3.1 In Vivo Methods: Genetic Complementation 52
3.3.2 In Vivo Methods: Chemical Complementation 53
3.3.3 In Vivo Methods: Surface Display 53
3.3.4 In Vitro Methods: Lysate Assay 55
3.3.5 In Vitro Methods: Ribosome Display 55
3.3.6 In Vitro Methods: In Vitro Compartmentalization 55
3.3.7 Equipment/Automation 56
3.4 Selected Industrial Examples 56
3.4.1 Activity 56
3.4.2 Thermostability 58
3.4.3 Substrate Specificity 58
3.4.4 Product Specificity 59
3.4.5 Enantioselectivity 59
3.5 Conclusions and Future Directions 60
4 Applications of Reaction Engineering to Industrial Biotransformations 65
4.1 Introduction 65
4.2 Metabolic Bioconversion 66
4.3 Enzymatic Biotransformations 67
4.3.1 Cofactor Regeneration 67
4.3.2 Racemic Mixtures 69
4.3.3 Equilibrium Conversion 72
4.3.4 By-Product Formation 76
4.3.5 Substrate Inhibition 79
4.3.6 Low Solubility 82
4.4 Conclusions 83
5 Chiral Synthesis of Pharmaceutical Intermediates Using Oxynitrilases 89
5.1 Introduction 89
5.2 HNL 89
5.2.1 The Natural Function and Distribution of HNLs 89
5.2.2 Classification of HNLs 91
5.2.3 New HNLs and High-Throughput Screening 93
5.3. Reaction of HNLs 95
5.3.1 Reaction System 95
5.3.2 Immobilization of Enzyme 97
5.3.3 Continuous Reactors 98
5.3.4 Henry Reaction 98
5.4 Transformation of Cyanohydrins 99
5.4.1 Transformation of Hydroxyl Group 99
5.4.2 Transformation of Nitrile Group 100
5.4.3 Intramolecular Reaction 102
5.5 Summary 104
6 Expanding the Scope of Aldolases as Tools for Organic Synthesis 111
6.1 Directed Evolution and Rational Mutagenesis 111
6.2 Reaction Engineering 114
6.3 Broad Substrate Tolerance of Wild-Type Aldolases 116
6.4 Conclusions 118
7 Synthetic Applications of Ketoreductases and Alcohol Oxidases 121
7.1 Ketoreductases 121
7.1.1 Wild-Type Whole-Cell Biocatalysts 122
7.1.2 Recombinant Whole-Cell Biocatalysts Overexpressing
Catalytic Enzymes 125
7.1.3 Isolated Enzyme 129
7.2 Alcohol Oxidases 142
7.2.1 Primary Alcohol Oxidases 142
7.2.2 Secondary Alcohol Oxidases 144
8 Applications of Nitrile Hydratases and Nitrilases 153
8.1 Introduction 153
8.2 NHase 153
8.2.1 New NHases 153
8.2.2 Applications 154
8.3 Nitrilase 163
8.3.1 New Nitrilases 163
8.3.2 Applications 167
8.4 Conclusions 178
9 Biosynthesis of Drug Metabolites 183
9.1 Introduction 183
9.2 Metabolite Synthesis Using Mammalian Bioreactors 184
9.2.1 Selection of In Vitro Systems 185
9.2.2 Reaction Condition Optimization 187
9.2.3 Large Scale Incubations 190
9.2.4 Examples with Mammalian Bioreactors 190
9.2.5 In Vivo Samples 192
9.3 Metabolite Synthesis Using Microbial Bioreactors 192
9.3.1 Microbial Bioreactors Used in Metabolite Structure Elucidation 193
9.3.2 Microbial Bioreactors Used in Synthesis of Key Metabolites 193
9.3.3 Strain Selection 194
9.3.4 Microbial Glycoside Conjugation 196
9.3.5 Large Scale Reactions 199
9.3.6 Examples for Metabolite Synthesis with a Microbial Bioreactor 200
9.4 Recombinant Enzyme Bioreactors 202
9.4.1 Advantages of Using CYP Enzymes for Producing
Drug Metabolites 202
9.4.2 Human Cytochrome Biocatalysts 205
9.4.3 Microbial CYP Enzymes 206
9.5 Summary 207
10 Application of Whole-Cell Biotransformation in the
Pharmaceutical Industry 213
10.1 Introduction 213
10.1.1 Whole-Cell Biotransformation Processes Used in Commercial
Production of Pharmaceuticals 214
10.1.2 Application of Whole-Cell Biotransformation Process in the
Synthesis of Chiral Pharmaceutical Intermediates 214
10.2 Disadvantages of Whole-Cell Process Compared with the Isolated
Enzyme Process 217
10.2.1 Substrate Availability and Recovery of Products in Low
Concentrations 217
10.2.2 Undesirable Side Reactions 217
10.2.3 Toxicity of Substrate and Product 217
10.3 Advantages of Whole-Cell Process Compared with the Isolated
Enzyme Process 218
10.3.1 More Stable Sources than Isolated Enzymes 218
10.3.2 Regeneration of Cofactors and Multi-Enzymes Reactions 218
10.3.3 Diversity and Availability 218
10.3.4 Reactions with Non-Commercially Available Isolated Enzymes
for Preparative Scale Synthesis 218
10.3.5 Cost Effectiveness and Ease of Operation 219
10.4 Approaches to Address the Disadvantages of Whole-Cell
Biotransformation 220
10.4.1 Control of Substrate and Product Concentration by
Absorbing Resins 220
10.4.2 Immobilized-Cell Technology 221
10.4.3 Aqueous-Organic Two-Phase System 222
10.4.4 Genetic Engineering Approaches 223
10.5 Conclusions 224
11 Combinatorial Biosynthesis of Pharmaceutical Natural Products 229
11.1 Introduction 229
11.2 Combinatorial Biosynthesis: The Natural Way for Structural Diversity 230
11.3 Examples of Combinatorial Biosynthesis of Pharmaceutical
Natural Products 234
11.3.1 Erythromycin (Polyketide Biosynthesis) 234
11.3.2 Daptomycin (Nonribosomal Peptide Biosynthesis) 236
11.3.3 Patellamide (Ribosomal Peptide Biosynthesis) 239
11.4 Summary and Perspectives 240
12 Metabolic Engineering for the Development and Manufacturing
of Pharmaceuticals 247
12.1 Introduction 247
12.2 Metabolic Engineering Tools 248
12.2.1 Tools for the Cellular Metabolic Network Analysis 248
12.2.2 Tools for Rational Genetic Modification 251
12.3 Metabolic Engineering for the Development and Production
of Polyketide Pharmaceuticals 253
12.3.1 Biosynthesis of Polyketides 253
12.3.2 Metabolic Engineering for Improved Erythromycin Production 253
12.3.3 Metabolic Engineering for Overproduction of 6dEB
in Heterologous Hosts 254
12.3.4 Metabolic Engineering of Other Polyketides 256
12.3.5 Development of Novel Polyketides for Drug Discovery 256
12.4 Metabolic Engineering for the Production of /3-Lactam 257
12.5 Metabolic Engineering for Isoprenoid Production 258
12.5.1 Biosynthesis Pathway of Isoprenoids 259
12.5.2 Metabolic Engineering for Enhancing Precursor Supply for
Isoprenoid Production 260
12.5.3 Metabolic Engineering for Artemisinine Development
and Production 261
12.5.4 Metabolic Engineering for Carotenoid Production 262
12.5.5 Metabolic Engineering for Taxol Development
and Production 262
12.6 Conclusions 265
13 Multimodular Synthases and Supporting Enzymes
for Chemical Production 273
13.1 Introduction 273
13.2 Background 274
13.2.1 Multimodular Synthase Architecture 274
13.2.2 Natural Product Biosynthetic Cycle 276
13.3 Metabolic Engineering of Megasynthases 277
13.3.1 Daptomycin: Metabolic Engineering by Domain Swap 278
13.3.2 Avermectin: Metabolic Engineering by Directed Fermentation 281
13.4 Excised Domains for Chemical Transformations 284
13.4.1 Function of Individual Domains, Domain Autonomy 284
13.4.2 Cyclization 285
13.4.3 Halogenation 288
13.4.4 Heterocyclization/Aromatization 290
13.4.5 Methylation 292
13.4.6 Oxygenation 294
13.4.7 Glycosylation 295
13.5 Conclusions 299
14 Green Chemistry with Biocatalysis for Production of Pharmaceuticals 305
14.1 Introduction 305
14.2 Enzymatic Resolutions: Higher Yields, Less Waste 309
14.3 Bioreductions: Greener Ligands, Renewable Hydride
Donors, No Metals 312
14.3.1 Enzymatic Oxidations: Clean, Highly Selective and Catalytic 314
14.4 C—C Bond Formations: Atom Efficiency at Its Best 316
14.5 Summary and Outlook 318
Index 323
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| spelling | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing Junhua (Alex) Tao ... [eds] Singapore [u.a.] Wiley 2009 X, 324 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Includes bibliographical references and index Pharmaceutical biotechnology Enzymes / Biotechnology Enzymes Biotechnology Pharmazeutische Industrie (DE-588)4045696-1 gnd rswk-swf Biokatalyse (DE-588)4393622-2 gnd rswk-swf Biokatalyse (DE-588)4393622-2 s Pharmazeutische Industrie (DE-588)4045696-1 s DE-604 Tao, Junhua Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=017612818&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing Pharmaceutical biotechnology Enzymes / Biotechnology Enzymes Biotechnology Pharmazeutische Industrie (DE-588)4045696-1 gnd Biokatalyse (DE-588)4393622-2 gnd |
| subject_GND | (DE-588)4045696-1 (DE-588)4393622-2 |
| title | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing |
| title_auth | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing |
| title_exact_search | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing |
| title_full | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing Junhua (Alex) Tao ... [eds] |
| title_fullStr | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing Junhua (Alex) Tao ... [eds] |
| title_full_unstemmed | Biocatalysis for the pharmaceutical industry discovery, development, and manufacturing Junhua (Alex) Tao ... [eds] |
| title_short | Biocatalysis for the pharmaceutical industry |
| title_sort | biocatalysis for the pharmaceutical industry discovery development and manufacturing |
| title_sub | discovery, development, and manufacturing |
| topic | Pharmaceutical biotechnology Enzymes / Biotechnology Enzymes Biotechnology Pharmazeutische Industrie (DE-588)4045696-1 gnd Biokatalyse (DE-588)4393622-2 gnd |
| topic_facet | Pharmaceutical biotechnology Enzymes / Biotechnology Enzymes Biotechnology Pharmazeutische Industrie Biokatalyse |
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