Redox biocatalysis: fundamentals and applications
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| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Hoboken, NJ
Wiley
2013
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| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Literaturangaben |
| Physical Description: | X, 537 S. graph. Darst. 25 cm |
| ISBN: | 9780470874202 0470874201 |
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Record in the Search Index
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|---|---|
| adam_text | Titel: Redox biocatalysis
Autor: Gamenara, Daniela
Jahr: 2013
CONTENTS
PREFACE ix
1. Enzymes Involved in Redox Reactions: Natural Sources and
Mechanistic Overview 1
1.1 Motivation: Green Chemistry and Biocatalysis 1
1.2 Sources of Biocatalysts 2
1.2.1 Plants and Animals as Sources of Redox Biocatalysts 3
1.2.2 Wild-Type Microorganisms 7
1.2.2.1 Yeasts 7
1.2.2.2 Fungi 8
1.2.2.3 Bacteria 8
1.2.3 Metagenomic Assessments 9
1.3 Overview of Redox Enzymes 10
1.3.1 Dehydrogenases 13
1.3.1.1 Zn-Dependent Dehydrogenases 14
1.3.1.2 Flavin-Dependent Dehydrogenases 15
1.3.1.3 Pterin-Dependent Dehydrogenases 16
1.3.1.4 Quinoprotein Dehydrogenases 17
1.3.1.5 Dehydrogenases without Prosthetic Group 18
1.3.2 Oxygenases 19
1.3.2.1 Monooxy genases 20
1.3.2.2 Dioxy genases 38
1.3.3 Oxidases 50
1.3.3.1 Iron-Containing Oxidases 5 0
1.3.3.2 Copper-Containing Oxidases 51
1.3.3.3 Flavin-Dependent Oxidases 56
1.3.4 Peroxidases 61
1.4 Concluding Remarks 64
References 64
2. Natural Cofactors and Their Regeneration Strategies 86
2.1 Types of Natural Cofactors-Mechanisms 86
2.2 Cofactor Regeneration 88
2.2.1 Enzymatic Regeneration of Reduced Cofactors 88
VI CONTENTS
2.2.1.1 Substrate-Assisted Method 88
2.2.1.2 Enzyme-Assisted Method 89
2.2.2 Enzymatic Regeneration of Oxidized Cofactors 92
2.2.3 Chemical Regeneration of Cofactors 94
2.2.4 Electrochemical Regeneration of Cofactors 95
2.2.5 Photochemical Regeneration of Cofactors 96
2.3 Concluding Remarks 97
References 98
3. Reactions Involving Dehydrogenases 101
3.1 General Considerations 101
3.2 Reduction of Carbonyl Groups 105
3.2.1 Reduction of Aliphatic and Aromatic Ketones 106
3.2.2 Reduction of a- and y0-keto Esters and Derivatives 119
3.2.3 Reduction of Diketones 126
3.2.4 Reduction of Aldehydes 128
3.3 Racemization and Deracemization Reactions 130
3.4 Preparation of Amines 135
3.5 Reduction of C-C Double Bonds 142
3.6 Oxidation Reactions 152
3.7 Dehydrogenase-Catalyzed Redox Reactions in
Natural Products 159
3.8 Concluding Remarks 164
References 165
4. Reactions Involving Oxygenases 180
4.1 Monooxygenase-Catalyzed Reactions 180
4.1.1 Hydroxylation of Aliphatic Compounds 181
4.1.2 Hydroxylation of Aromatic Compounds 187
4.1.3 Baeyer-Villiger Reactions 189
4.1.3.1 Classification and Metabolic Role of BVMOs 192
4.1.3.2 Isolated Enzymes versus Whole-Cell Systems
(Wild-Type and Recombinant Microorganisms) 194
4.1.3.3 Substrate Profile of Available Baeyer-Villiger
Monooxy genases 195
4.1.3.4 Synthetic Applications of BVMOs 201
4.1.4 Epoxidation of Alkenes 240
4.2 Dioxygenase-Catalyzed Reactions 251
4.2.1 Aromatic Dioxygenases 251
4.2.1.1 Dihydroxylation of Aromatic Compounds 251
4.2.1.2 Other Oxidation Reactions Performed by
Aromatic Dioxygenases 274
4.2.2 Miscellaneous Dioxygenases 279
4.2.2.1 Lipoxygenase 279
CONTENTS VII
4.3 Concluding Remarks 285
References 286
5. Reactions Involving Oxidases and Peroxidases 303
5.1 Oxidase-Catalyzed Reactions 304
5.1.1 Oxidases Acting on C-0 Bonds 304
5.1.1.1 Galactose Oxidase 304
5.1.1.2 Pyranose Oxidase 308
5.1.1.3 Alcohol Oxidase 311
5.1.1.4 Glucose Oxidase 313
5.1.1.5 Glycolate Oxidase 313
5.1.2 Laccases and Tyrosinases (Phenol Oxidases) 315
5.1.2.1 Laccase 315
5.1.2.2 Tyrosinase and Other Polyphenol Oxidases 352
5.1.3 Oxidases Acting on C-N Bonds 361
5.1.3.1 D-AminoAcid Oxidase 361
5.1.3.2 L-Amino Acid Oxidase 368
5.1.3.3 Monoamine Oxidase 368
5.1.3.4 Copper Amine Oxidases 371
5.1.4 Miscellaneous 371
5.1.4.1 Cholesterol Oxidase 372
5.1.4.2 Vanillyl Alcohol Oxidase 373
5.1.4.3 Alditol Oxidase 373
5.2 Peroxidase-Catalyzed Reactions 375
5.2.1 Peroxidase Mediated Transformations 379
5.2.1.1 Oxidative Dehydrogenation (2 RH + H202 -
2 R* + 2 H20 ^R-R) 379
5.2.1.2 Oxidative Halogenation (RH + H202 +X +
H+^RX + 2H20) 385
5.2.1.3 Oxygen-Transfer Reactions (RH + H202 -*
ROH + H20) 390
5.3 Concluding Remarks 403
References 404
6. Hydrolase-Mediated Oxidations 433
6.1 Hydrolase Promiscuity and in situ Peracid Formation.
Perhydrolases vs. Hydrolases. Other Promiscuous
Hydrolase-Mediated Oxidations 433
6.2 Hydrolase-Mediated Bulk Oxidations in Aqueous Media (e.g.,
Bleaching, Disinfection, etc.) 436
6.3 Lipase-Mediated Oxidations: Prileshajev Epoxidations and
Baeyer-Villiger Reactions 439
6.4 Hydrolase-Mediated Oxidation and Processing of Lignocellulosic
Materials 445
VIII CONTENTS
6.5 Concluding Remarks 448
References 448
7. Bridging Gaps: From Enzyme Discovery to Bioprocesses 453
7.1 Context 453
7.2 Enzyme Directed Evolution and High-Throughput-Screening of
Biocatalysts 454
7.3 Successful Case: Baker s Yeast Redox Enzymes, Their Cloning,
and Separate Overexpression 467
7.4 Whole-Cells vs. Isolated Enzymes: Medium Engineering 473
7.5 Beyond: Multistep Domino Biocatalytic Processes 477
7.6 Concluding Remarks 482
References 483
8. Industrial Applications of Biocatalytic Redox Reactions: From
Academic Curiosities to Robust Processes 487
8.1 Motivation: Drivers for Industrial Biocatalytic Processes 487
8.2 Key Aspects in Industrial Biocatalytic Processes 488
8.3 Industrial Biocatalytic Redox Processes: Free Enzymes 492
8.4 Industrial Biocatalytic Redox Processes-Whole-Cells: The
Designer Bug Concept and Beyond (Metabolic Engineering) 500
8.5 Concluding Remarks and Future Perspectives 511
References 516
INDEX 521
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| spelling | Redox biocatalysis fundamentals and applications Daniela Gamenara ... Hoboken, NJ Wiley 2013 X, 537 S. graph. Darst. 25 cm txt rdacontent n rdamedia nc rdacarrier Literaturangaben Redoxreaktion (DE-588)4177303-2 gnd rswk-swf Biokatalyse (DE-588)4393622-2 gnd rswk-swf Enzymes--Biotechnology. Oxidation-reduction reaction. Biokatalyse (DE-588)4393622-2 s Redoxreaktion (DE-588)4177303-2 s DE-604 Gamenara, Daniela Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025726539&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Redox biocatalysis fundamentals and applications Redoxreaktion (DE-588)4177303-2 gnd Biokatalyse (DE-588)4393622-2 gnd |
| subject_GND | (DE-588)4177303-2 (DE-588)4393622-2 |
| title | Redox biocatalysis fundamentals and applications |
| title_auth | Redox biocatalysis fundamentals and applications |
| title_exact_search | Redox biocatalysis fundamentals and applications |
| title_full | Redox biocatalysis fundamentals and applications Daniela Gamenara ... |
| title_fullStr | Redox biocatalysis fundamentals and applications Daniela Gamenara ... |
| title_full_unstemmed | Redox biocatalysis fundamentals and applications Daniela Gamenara ... |
| title_short | Redox biocatalysis |
| title_sort | redox biocatalysis fundamentals and applications |
| title_sub | fundamentals and applications |
| topic | Redoxreaktion (DE-588)4177303-2 gnd Biokatalyse (DE-588)4393622-2 gnd |
| topic_facet | Redoxreaktion Biokatalyse |
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