Enzyme-Based Organic Synthesis

ISBN-13: 9781118027943 / Angielski / Twarda / 2022 / 544 str.

Cheanyeh Cheng

Opis

This book discusses the methods and applications of enzymatic and microbial processes for organic synthesis, in particular asymmetric synthesis. Coverage also includes basic principles associated of enzyme specificity and catalytic abilities. The author details organic syntheses with the main classes of enzymes, illustrating their important characteristics of substrate and chemical specificity, regioselectivity, and stereoselectivity that these enzymes bring to organic synthesis. Applications for pharmaceutical and medicinal industry, food industry, cosmetics, fragrance, and health care are also described.

Spis treści

Preface xiAcknowledgements xv1 Introduction 11.1 Discovery and Nature of Enzyme 11.2 Enzyme Structure and Catalytic Function 21.2.1 Enzyme Structure 21.2.2 Catalytic Function 31.3 Cofactors and Coenzymes 51.4 Molecular Recognition and Enzyme Specificity 61.4.1 Substrate Specificity 71.4.2 Regiospecificity 91.4.3 Stereospecificity 101.5 Enzyme Classes and Nomenclature 131.6 Enzyme and Green Chemistry 151.7 The Winner of Year 2010: Greener Manufacturing of Sitagliptin Enabled by an Evolved Transaminase 171.8 The Winner of Year 2009: A Solvent-Free Biocatalytic Process for Cosmetic and Personal Care Ingredients 17References 182 Organic Synthesis with Oxidoreductases 212.1 Oxidation Reactions 212.1.1 Oxidation of Alcohols and Aldehydes 212.1.2 Hydroxylation of Alkanes 262.1.3 Hydroxylation of Aromatic Compounds 292.1.4 Dihydroxylation of Aromatic Compounds 312.1.5 Epoxidation 352.1.6 Sulfoxidation Reactions 382.1.7 Baeyer-Villiger Reactions 392.1.8 Peroxidation Reactions 412.2 Reduction Reactions 442.2.1 Reduction of Aldehydes and Ketones 442.2.2 Reduction of C=C Bonds 50References 553 Organic Synthesis with Transferases 633.1 Transamination with Aminotransferases 633.2 Glycosyl-transfer with glycosyltransferase 683.3 Phosphorylation with Kinases 733.4 Acetyl Group Transfer with Acetyltransferase 75References 784 Organic Synthesis with Hydrolases 834.1 Hydrolysis of Ester Bond 834.1.1 Ester Hydrolysis with Esterases 834.1.2 Ester Hydrolysis with Lipases 894.1.3 Ester Hydrolysis with Proteases 944.2 Hydrolysis of Amide Bond 974.3 Hydrolysis of Phosphate Esters 1034.4 Hydrolysis of Epoxides 1054.5 Hydrolysis of Hydantoins 1114.6 Hydrolysis of Glycosidic Bonds and Natural Polysaccharide 1184.6.1 Hydrolysis of Starch and Applications 1194.6.2 Hydrolysis of Cellulose and Applications 1214.6.3 Hydrolysis of Hemicellulose and Applications 127References 1295 Organic Synthesis with Lyases 1395.1 Lyases with Carbon-Carbon Bonds 1395.1.1 Aldolases in Organic Syntheses 1395.1.2 Enzymatic Acyloin Condensation 1455.1.2.1 Acyloin Condensation Catalyzed by Pyruvate Decarboxylase 1465.1.2.2 Acyloin Condensation Catalyzed by Benzoylformate Decarboxylase 1475.1.2.3 Acyloin Condensation Catalyzed by Benzaldehyde Lyase 1485.1.2.4 Acyloin Condensation Catalyzed by Phenylpyruvate Decarboxylase 1515.1.3 Cyanohydrin Formation with Hydroxynitrile Lyases 1525.2 Lyases with Carbon-Oxygen Bonds 1585.2.1 Enzyme-Catalyzed Water Addition to Electron-Rich C=C Bonds 1595.2.1.1 Oleate Hydratase 1595.2.1.2 Linalool Dehydratase-Isomerase 1625.2.1.3 Limonene Hydratase 1635.2.2 Enzyme-Catalyzed Water Addition to Electron-Deficient C=C Bonds 1645.2.2.1 Fumarase 1645.2.2.2 Malease 1665.2.2.3 Enoyl-CoA Hydratase 1675.3 Lyases with Carbon-Nitrogen Bonds 1695.3.1 Aspartate Ammonia Lyase 1705.3.2 Methylaspartate Ammonia Lyase 1735.3.3 Aromatic Amino Acid Ammonia Lyases 1755.3.3.1 l-Arylalanines Synthesis 1765.3.3.2 d-Arylalanines Synthesis 1805.3.3.3 ß-Arylalanines Synthesis 1825.3.3.4 Applications for Arylalanines Synthesis 1845.4 Lyases with Carbon-Sulfur Bonds 1885.5 Lyases with Carbon-Halide Bonds 1935.5.1 Synthesis of Chiral Epoxides 1945.5.2 Synthesis of Enantiopure ß-Substituted Alcohols 1965.5.3 Application of Cascade Reactions 202References 2056 Organic Synthesis with Isomerases 2216.1 Racemases and Epimerases 2216.1.1 Amino Acid Racemases and Epimerases 2216.1.1.1 d-Amino Acid Synthesis with PLP-Dependent Amino Acid Racemases 2236.1.1.2 d-Amino Acid Synthesis with PLP-Independent Amino Acid Racemases 2246.1.1.3 Amino Acid Racemases with Broad Substrate Specificity 2266.1.1.4 Applications of Amino Acid Racemases and Epimerases 2286.1.2 Hydroxy Acid Racemases and Epimerases 2296.1.2.1 Lactate Racemase 2296.1.2.2 Mandelate Racemase 2306.1.3 N-Acetyl-d-glucosamine 2- epimerase 2356.1.4 Hydantoin Racemase 2386.2 Cis-Trans Isomerase 2426.2.1 Maleate Cis-Trans Isomerase 2426.2.2 Linoleate Isomerase 2446.3 Intramolecular Oxidoreductases 2476.3.1 Aldose-Ketose isomerases 2476.3.1.1 Xylose (Glucose) Isomerase 2476.3.1.2 l-Rhamnose Isomerase 2566.3.1.3 l-Fucose Isomerase 2616.4 Intramolecular Transferases 2656.4.1 Phosphopentomutase 2656.4.2 Lysine 2,3-Aminomutase 2706.4.3 Lysine 5,6-Aminomutase 2746.4.4 Tyrosine 2,3-Aminomutase 2756.4.5 Phenylalanine Aminomutase 2786.4.5.1 l-ß-Phenylalanine Forming 2786.4.5.2 d-ß-Phenylalanine Forming 2826.5 Intramolecular Lyases 2876.5.1 ent-Copalyl Diphosphate Synthase 2876.5.2 Lycopene ß-Cyclase 294References 3047 Organic Synthesis with Ligases 3217.1 Ligases for Carbon-Oxygen Bonds Formation 3217.1.1 Olefin ß-Lactone Synthetase 3217.2 Ligases for Carbon-Sulfur Bonds Formation 3237.2.1 Acetate-CoA Ligase (AMP-forming) 3237.2.2 Medium-chain Acyl-CoA Ligase 3317.2.3 Long-chain-fatty-acid-CoA Ligase 3407.3 Ligases for Carbon-Nitrogen Bonds Formation 3477.3.1 Glutamine Synthetase 3477.3.2 l-Alanine-l-anticapsin Ligase 3557.3.3 Carbapenam-3-carboxylate Synthase 3597.4 Ligases for Carbon-Carbon Bonds Formation 3637.4.1 Pyruvate Carboxylase 3637.4.2 Acetyl-CoA Carboxylase 383References 4148 Future Perspectives 4318.1 Combinatorial Enzymatic Organic Synthesis 4318.1.1 Combinatorial Chemistry 4318.1.2 Principle of Combinatorial Chemistry 4328.1.3 Combinatorial Chemistry with Enzymes 4338.1.3.1 Enzymes as a Tool in Combinatorial Synthesis 4348.1.3.2 Combinatorial Biocatalysis 4378.1.3.3 Combinatorial Biosynthesis 4458.2 Artificial Intelligence Assisted Enzymatic Organic Synthesis 4528.2.1 Introduction to Artificial Intelligence 4528.2.2 Categorization of Artificial Intelligence 4538.2.3 Machine Learning 4548.2.4 Artificial Intelligence with Enzymatic Organic Synthesis 455References 460Index 465

O autorze

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.