Enzyme-Based Organic Synthesis

Enzyme-Based Organic Synthesis
 
An insightful exploration of an increasingly popular technique in organic chemistry
 
In Enzyme-Based Organic Synthesis, expert chemist Dr. Cheanyeh Cheng delivers a comprehensive discussion of the principles, methods, and applications of enzymatic and microbial processes for organic synthesis. The book thoroughly explores this growing area of green synthetic organic chemistry, both in the context of academic research and industrial practice.
 
The distinguished author provides a single point of access for enzymatic methods applicable to organic synthesis and focuses on enzyme catalyzed organic synthesis with six different classes of enzyme. This book serves as a link between enzymology and biocatalysis and serves as an invaluable reference for the growing number of organic chemists using biocatalysis.
 
Enzyme-Based Organic Synthesis provides readers with multiple examples of practical applications of the main enzyme classes relevant to the pharmaceutical, medical, food, cosmetics, fragrance, and health care industries.
 
Readers will also find:
* A thorough introduction to foundational topics, including the discovery and nature of enzymes, enzyme structure, catalytic function, molecular recognition, enzyme specificity, and enzyme classes
* Practical discussions of organic synthesis with oxidoreductases, including oxidation reactions and reduction reactions
* Comprehensive explorations of organic synthesis with transferases, including transamination with aminotransferases and phosphorylation with kinases
* In-depth examinations of organic synthesis with hydrolases, including the hydrolysis of the ester bond
 
Perfect for organic synthetic chemists, chemical and biochemical engineers, biotechnologists, process chemists, and enzymologists, Enzyme-Based Organic Synthesis is also an indispensable resource for practitioners in the pharmaceutical, food, cosmetics, and fragrance industries that regularly apply this type of synthesis.

Inhaltsverzeichnis

Preface xi
 
Acknowledgements xv
 
1 Introduction 1
 
1.1 Discovery and Nature of Enzyme 1
 
1.2 Enzyme Structure and Catalytic Function 2
 
1.2.1 Enzyme Structure 2
 
1.2.2 Catalytic Function 3
 
1.3 Cofactors and Coenzymes 5
 
1.4 Molecular Recognition and Enzyme Specificity 6
 
1.4.1 Substrate Specificity 7
 
1.4.2 Regiospecificity 9
 
1.4.3 Stereospecificity 10
 
1.5 Enzyme Classes and Nomenclature 13
 
1.6 Enzyme and Green Chemistry 15
 
1.7 The Winner of Year 2010: Greener Manufacturing of Sitagliptin Enabled by an Evolved Transaminase 17
 
1.8 The Winner of Year 2009: A Solvent-Free Biocatalytic Process for Cosmetic and Personal Care Ingredients 17
 
References 18
 
2 Organic Synthesis with Oxidoreductases 21
 
2.1 Oxidation Reactions 21
 
2.1.1 Oxidation of Alcohols and Aldehydes 21
 
2.1.2 Hydroxylation of Alkanes 26
 
2.1.3 Hydroxylation of Aromatic Compounds 29
 
2.1.4 Dihydroxylation of Aromatic Compounds 31
 
2.1.5 Epoxidation 35
 
2.1.6 Sulfoxidation Reactions 38
 
2.1.7 Baeyer-Villiger Reactions 39
 
2.1.8 Peroxidation Reactions 41
 
2.2 Reduction Reactions 44
 
2.2.1 Reduction of Aldehydes and Ketones 44
 
2.2.2 Reduction of C=C Bonds 50
 
References 55
 
3 Organic Synthesis with Transferases 63
 
3.1 Transamination with Aminotransferases 63
 
3.2 Glycosyl-transfer with glycosyltransferase 68
 
3.3 Phosphorylation with Kinases 73
 
3.4 Acetyl Group Transfer with Acetyltransferase 75
 
References 78
 
4 Organic Synthesis with Hydrolases 83
 
4.1 Hydrolysis of Ester Bond 83
 
4.1.1 Ester Hydrolysis with Esterases 83
 
4.1.2 Ester Hydrolysis with Lipases 89
 
4.1.3 Ester Hydrolysis with Proteases 94
 
4.2 Hydrolysis of Amide Bond 97
 
4.3 Hydrolysis of Phosphate Esters 103
 
4.4 Hydrolysis of Epoxides 105
 
4.5 Hydrolysis of Hydantoins 111
 
4.6 Hydrolysis of Glycosidic Bonds and Natural Polysaccharide 118
 
4.6.1 Hydrolysis of Starch and Applications 119
 
4.6.2 Hydrolysis of Cellulose and Applications 121
 
4.6.3 Hydrolysis of Hemicellulose and Applications 127
 
References 129
 
5 Organic Synthesis with Lyases 139
 
5.1 Lyases with Carbon-Carbon Bonds 139
 
5.1.1 Aldolases in Organic Syntheses 139
 
5.1.2 Enzymatic Acyloin Condensation 145
 
5.1.2.1 Acyloin Condensation Catalyzed by Pyruvate Decarboxylase 146
 
5.1.2.2 Acyloin Condensation Catalyzed by Benzoylformate Decarboxylase 147
 
5.1.2.3 Acyloin Condensation Catalyzed by Benzaldehyde Lyase 148
 
5.1.2.4 Acyloin Condensation Catalyzed by Phenylpyruvate Decarboxylase 151
 
5.1.3 Cyanohydrin Formation with Hydroxynitrile Lyases 152
 
5.2 Lyases with Carbon-Oxygen Bonds 158
 
5.2.1 Enzyme-Catalyzed Water Addition to Electron-Rich C=C Bonds 159
 
5.2.1.1 Oleate Hydratase 159
 
5.2.1.2 Linalool Dehydratase-Isomerase 162
 
5.2.1.3 Limonene Hydratase 163
 
5.2.2 Enzyme-Catalyzed Water Addition to Electron-Deficient C=C Bonds 164
 
5.2.2.1 Fumarase 164
 
5.2.2.2 Malease 166
 
5.2.2.3 Enoyl-CoA Hydratase 167
 
5.3 Lyases with Carbon-Nitrogen Bonds 169
 
5.3.1 Aspartate Ammonia Lyase 170
 
5.3.2 Methylaspartate Ammonia Lyase 173
 
5.3.3 Aromatic Amino Acid Ammonia Lyases 175
 
5.3.3.1 l-Arylalanines Synthesis 176
 
5.3.3.2 d-Arylalanines Synthesis 180
 
5.

Über den Autor / die Autorin

Cheanyeh Cheng, PhD, obtained his doctorate from the Department of Chemical and Biochemical Engineering at Rutgers University in 1987 and is Professor of Chemistry at Chung Yuan Christian University in Taiwan. His research covers the fields of bioorganic chemistry and biotransformation, analytical chemistry, and biosensors. He owns 15 patents from Taiwan, the United States of America, Japan, and the European Union.

Zusammenfassung

An insightful exploration of an increasingly popular technique in organic chemistry

In Enzyme-Based Organic Synthesis, expert chemist Dr. Cheanyeh Cheng delivers a comprehensive discussion of the principles, methods, and applications of enzymatic and microbial processes for organic synthesis. The book thoroughly explores this growing area of green synthetic organic chemistry, both in the context of academic research and industrial practice.

The distinguished author provides a single point of access for enzymatic methods applicable to organic synthesis and focuses on enzyme catalyzed organic synthesis with six different classes of enzyme. This book serves as a link between enzymology and biocatalysis and serves as an invaluable reference for the growing number of organic chemists using biocatalysis.

Enzyme-Based Organic Synthesis provides readers with multiple examples of practical applications of the main enzyme classes relevant to the pharmaceutical, medical, food, cosmetics, fragrance, and health care industries.

Readers will also find:
* A thorough introduction to foundational topics, including the discovery and nature of enzymes, enzyme structure, catalytic function, molecular recognition, enzyme specificity, and enzyme classes
* Practical discussions of organic synthesis with oxidoreductases, including oxidation reactions and reduction reactions
* Comprehensive explorations of organic synthesis with transferases, including transamination with aminotransferases and phosphorylation with kinases
* In-depth examinations of organic synthesis with hydrolases, including the hydrolysis of the ester bond

Perfect for organic synthetic chemists, chemical and biochemical engineers, biotechnologists, process chemists, and enzymologists, Enzyme-Based Organic Synthesis is also an indispensable resource for practitioners in the pharmaceutical, food, cosmetics, and fragrance industries that regularly apply this type of synthesis.

Produktdetails

• Autoren: C Cheng, Cheanyeh Cheng, Cheng Cheanyeh
• Verlag: Wiley, John and Sons Ltd
• Sprache: Englisch
• Produktform: Fester Einband
• Erschienen: 25.02.2022
• EAN: 9781118027943
• ISBN: 978-1-118-02794-3
• Seiten: 544
• Themen: Naturwissenschaften, Medizin, Informatik, Technik > Chemie > Organische Chemie; Chemie, Katalyse, chemistry, Catalysis, Organische Synthese, BIOCATALYSIS, BIOKATALYSE, Methods - Synthesis & Techniques, Organische Chemie / Methoden, Synthesen, Verfahren