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.

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.

Preface

Acknowledgements

Chapter 01 Introduction

1.1  Discovery and nature of enzyme

1.2  Enzyme structure and catalytic function

1.2.1       Enzyme structure

1.2.2       Catalytic function

1.3  Cofactors and coenzymes

1.4  Molecular recognition and enzyme specificity

1.4.1       Substrate specificity

1.4.2       Regiospecificity

1.4.3       Stereo-specificity

1.5  Enzyme classes and nomenclature

1.6  Enzyme and green chemistry

Chapter 02 Organic Synthesis with Oxidoreductases

2.1 Oxidation reactions

2.1.1  Oxidation of alcohols and aldehydes

2.1.2  Hydroxylation of alkanes

2.1.3  Hydroxylation of aromatic compounds

2.1.4  Dihydroxylation of aromatic compounds

2.1.5  Epoxidation

2.1.6  Sulfoxidation reactions

2.1.7  Baeyer-Villiger reactions

2.1.8  Peroxidation reactions

2.2 Reduction reactions

2.2.1  Reduction of aldehydes and ketones

2.2.2  Reduction of C=C bonds

Bibliography

Chapter 3 Organic Synthesis with Transferases

3.1 Transamination with Aminotransferases

3.2 Glycosyl-transfer with glycosyltransferase

3.3 Phosphorylation with kinases

3.4 Acetyl group transfer with acetyltransferase

Bibliography

Chapter 4 Organic Synthesis with Hydrolases

4.1 Hydrolysis of ester bond

4.1.1 Ester hydrolysis with esterases

4.1.2 Ester hydrolysis with lipases

4.1.3 Ester hydrolysis with proteases

4.2 Hydrolysis of amide bond

4.3 Hydrolysis of phosphate esters

4.4 Hydrolysis of epoxides

4.5 Hydrolysis of hydantoins

4.6 Hydrolysis of glycosidic bonds and natural polysaccharides

4.6.1 Hydrolysis of starch and applications

4.6.2 Hydrolysis of cellulose and applications

4.6.3 Hydrolysis of hemicellulose and applications

Bibliography

Chapter 5 Organic Synthesis with Lyases

5.1 Lyases with carbon-carbon bonds

5.1.1 Aldolases in organic syntheses

5.1.2 Enzymatic acyloin condensation

5.1.2.1 Acyloin condensation catalyzed by pyruvate decarboxylase

5.1.2.2 Acyloin condensation catalyzed by benzoylformate decarboxylase

5.1.2.3 Acyloin condensation catalyzed by benzaldehyde lyase

5.1.2.4 Acyloin condensation catalyzed by phenylpyruvate decarboxylase

5.1.3 Cyanohydrin formation with hydroxynitrile lyases

5.2 Lyases with carbon-oxygen bonds

5.2.1 Enzyme-catalyzed water addition to electron-rich C=C bonds

5.2.1.1 Oleate hydratase

5.2.1.2 Linalool dehydratase-isomerase

5.2.1.3 Limonene hydratase

5.2.2 Enzyme-catalyzed water addition to electron-deficient C=C bonds

5.2.2.1 Fumarase

5.2.2.2 Malease

5.2.2.3 Enoyl-CoA hydratase

5.3 Lyases with carbon-nitrogen bonds

5.3.1 Aspartate ammonia lyase

5.3.2 Methylaspartate ammonia lyase

5.3.3 Aromatic amino acid ammonia lyases

5.3.3.1 L-Arylalanines synthesis

5.3.3.2 D-Arylalanines synthesis

5.3.3.3 b-Arylalanines synthesis

5.3.3.4 Applications for arylalanines synthesis

5.4 Lyases with carbon-sulfur bonds

5.5 Lyases with carbon-halide bonds

5.5.1 Synthesis of chiral epoxides

5.5.2 Synthesis of enantiopure β-substituted alcohols

5.5.3 Application of cascade reactions

Bibliography

Chapter 6 Organic Synthesis with Isomerases

6.1 Amino acid racemases not requiring cofactors

6.2 Amino acid racemases requiring pyridoxal 5’-phosphate

6.3 Mandelate racemase

6.4 Isopenicillin N epimerase

6.5 Aldose-ketose isomerases

6.6 L-Rhamnose isomerase

6.7 L-fucose isomerase

6.8 N-Acetyl-D-glucosamine 2- epimerase

6.9 Allylic isomeriation

6.10 Maleylacetoacetate isomerase

6.11 Retinol isomerase

6.12 Maleate cis-trans isomerase

6.13 Unsaturated fatty acid cis-trans isomerase

Bibliography

Chapter 7 Organic Synthesis with Ligases

7.1 Aldol reactions with aldolases

7.2 Keto and aldol transfer reactions with transketolase

7.3 Dehydroquinate synthase

7.4 Thiolase

7.5 Isoprenoid synthesis

Bibliography

Chapter 8 Future Perspectives

8.1 Monooxygenation and dioxygenation

8.2 Substitutions

8.3 Formylation, hydroxymethylation, methylation

8.4 Rearrangements

Bibliography

Index

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