Redox Biocatalysis - Fundamentals and Applications

Paves the way for new industrial applications using redox biocatalysis
 
Increasingly, researchers rely on the use of enzymes to perform redox processes as they search for novel industrial synthetic routes. In order to support and advance their investigations, this book provides a comprehensive and current overview of the use of redox enzymes and enzyme-mediated oxidative processes, with an emphasis on the role of redox enzymes in chemical transformations. The authors examine the full range of topics in the field, from basic principles to new and emerging research and applications. Moreover, they explore everything from laboratory-scale procedures to industrial manufacturing.
 
Redox Biocatalysis begins with a discussion of the biochemical features of redox enzymes as well as cofactors and cofactor regeneration methods. Next, the authors present a variety of topics and materials to the research and development of full-scale industrial applications, including:
* Biocatalytic applications of redox enzymes such as dehydrogenases, oxygenases, oxidases, and peroxidases
* Enzyme-mediated oxidative processes based on biocatalytic promiscuity
* All the steps from enzyme discovery to robust industrial processes, including directed evolution, high-throughput screening, and medium engineering
* Case studies tracing the development of industrial applications using biocatalytic redox reactions
 
Each chapter ends with concluding remarks, underscoring the key scientific principles and processes. Extensive references serve as a gateway to the growing body of research in the field.
 
Researchers in both academia and industry will find this book an indispensable reference for redox biotransformations, guiding them from underlying core principles to new discoveries and emerging industrial applications.

Table des matières

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 Monooxygenases 20
 
1.3.2.2 Dioxygenases 38
 
1.3.3 Oxidases 50
 
1.3.3.1 Iron-Containing Oxidases 50
 
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
 
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 alpha- and ß-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 Monooxygenases 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
 
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-O 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

A propos de l'auteur

Daniela Gamenara, PhD, is Assistant Professor in the Organic Chemistry Department of the Faculty of Chemistry of Universidad de la República, Uruguay. After two short postdoctoral internships, her current scientific interest is the development of enzymatic methodologies for the synthesis of high added-value compounds and natural products as well, together with the use of new trends in organocatalysis for the same purposes.
Gustavo A. Seoane, PhD, is Full Professor and Head of the Organic Chemistry Department of the Faculty of Chemistry of Universidad de la República, Uruguay. His main scientific interest is the use of green procedures for the synthesis of bioactive natural products and analogs, in particular, intensive use of biotransformations to prepare polyoxygenated targets. He works actively to promote the development of biocatalysis in South America.
Patricia Saenz-Méndez, PhD, is Assistant Professor of Physical Organic Chemistry in the Faculty of Chemistry of Universidad de la República, Uruguay. She was previously appointed as postdoctoral fellow at the Örebro University, Sweden, and the National University of Ireland, Galway. Her work is devoted to the experimental and in silico development of biotechnological and organocatalytic tools for the preparation of high added-value chemicals and natural products.
Pablo Domínguez de María, PhD, is Group Leader at the Institute for Technical and Macromolecular Chemistry (ITMC), RWTH Aachen University, Germany. He was previously affiliated with AkzoNobel BV in the Netherlands and Degussa AG in Germany. Dr. Domínguez de María has also worked as a technical freelance advisor on emerging technologies (e.g., catalysis) applied to sustainable chemistry (www.sustainablemomentum.net). He was awarded the Young Scientist Prize by the Iberoamerican Academy of Pharmacy.

Résumé

Presenting the state of the art of biocatalysis and its interdisciplinary nature, this book covers the full range of topics in the field, from basic principles to forefront research, and from laboratory-scale procedures to chemical manufacturing at industrial-scale.

Détails du produit

• Auteurs: Pablo Dom?nguez De Mar?a, Pablo Gamenara Dominguez De Maria, Pablo Domínguez De María, DOMINGUEZ DE MARIA PABLO GAMENARA, D Gamenara, Daniel Gamenara, Daniela Gamenara, Daniela (Universidad De La Republica Gamenara, Daniela Seoane Gamenara, Daniela/ Seoane Gamenara, Gamenara Daniela, Patricia Saenz M?ndez, Patricia Saenz Mendez, Pa Saenz Méndez, Patricia Saenz Méndez, Gustav Seoane, Gustavo Seoane, Gustavo A. Seoane, Seoane Gustavo
• Edition: Wiley, John and Sons Ltd
• Langues: Anglais
• Format d'édition: Livre Relié
• Sortie: 16.11.2012
• EAN: 9780470874202
• ISBN: 978-0-470-87420-2
• Pages: 552
• Catégories: Sciences naturelles, médecine, informatique, technique > Chimie > Autres; Chemie, Katalyse, chemistry, BIOCATALYSIS, BIOKATALYSE, Chemical Engineering, chemische Verfahrenstechnik, Bioorganic Chemistry, Allg. Chemische Verfahrenstechnik, Bioorganische Chemie