Biotransformations in organic chemistry : a textbook

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Bibliographic Information

Biotransformations in organic chemistry : a textbook

Kurt Faber

Springer, c2018

7th extended and corr. ed

Available at  / 2 libraries

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Includes bibliographical references and index

Description and Table of Contents

Description

This well-established textbook on biocatalysis provides a basis for undergraduate and graduate courses in modern organic chemistry, as well as a condensed introduction into this field. After a basic introduction into the use of biocatalysts-principles of stereoselective transformations, enzyme properties and kinetics-the different types of reactions are explained according to the 'reaction principle', such as hydrolysis, reduction, oxidation, C-C bond formation, etc. Special techniques, such as the use of enzymes in organic solvents, immobilization techniques, artificial enzymes and the design of cascade-reactions are treated in a separate section. A final chapter deals with the basic rules for the safe and practical handling of biocatalysts. The use of biocatalysts, employed either as isolated enzymes or whole microbial cells, offers a remarkable arsenal of highly selective transformations for state-of-the-art synthetic organic chemistry. Over the last two decades, this methodology has become an indispensable tool for asymmetric synthesis, not only at the academic level, but also on an industrial scale. In this 7th edition new topics have been introduced which include alcohol and amine oxidases, amine dehydrogenases, imine reductases, haloalkane dehalogenases, ATP-independent phosphorylation, Michael-additions and cascade reactions. This new edition also emphasizes the use of enzymes in industrial biotransformations with practical examples.

Table of Contents

1 Introduction and Background Information 1.1 Introduction.......................................................................................... 1.2 Common Prejudices Against Enzymes............................................... 1.3 Advantages and Disadvantages of Biocatalysts.................................. 1.3.1 Advantages of Biocatalysts........................................................ 1.3.2 Disadvantages of Biocatalysts................................................... 1.3.3 Isolated Enzymes vs. Whole Cell Systems......................... 1.4 Enzyme Properties and Nomenclature............................................... 1.4.1 Structural Biology in a Nutshell.............................. 1.4.2 Mechanistic Aspects of Enzyme Catalysis........................... 1.4.3 Classification and Nomenclature............................................ 1.4.4 Coenzymes....................................................................... 1.4.5 Enzyme Sources.............................................................. References..... ................................................................................... 2 Biocatalytic Applications 2.1 Hydrolytic Reactions.......................................................................... 2.1.1 Mechanistic and Kinetic Aspects............................................. 2.1.2 Hydrolysis of the Amide Bond................................................ 2.1.3 Ester Hydrolysis....................................................................... 2.1.3.1 Esterases and Proteases............................................. 2.1.3.2 Lipases....................................................................... 2.1.3.3 Hydrolysis of Lactones....................................................................... 2.1.4 Hydrolysis and Formation of Phosphate Esters...................... 2.1.5 Hydrolysis of Epoxides........................................................... 2.1.6 Hydrolysis of Nitriles.............................................................. 2.2 Reduction Reactions.......................................................................... 2.2.1 Recycling of Cofactors............................................................ 2.2.2 Reduction of Aldehydes and Ketones Using Isolated Enzymes..................................................... 2.2.3 Reduction of Aldehydes and Ketones Using Whole Cells.... 2.2.4 Reduction of C=N Bonds ....................... 2.2.5 Reduction of C=C-Bonds ....................... 2.3 Oxidation Reactions.......................................................................... 2.3.1 Oxidation of Alcohols and Aldehydes................................... 2.3.2 Oxidation of Amines ................................... 2.3.3 Oxygenation Reactions........................................................... 2.3.3.1 Hydroxylation of Alkanes........................................ 2.3.3.2 Hydroxylation of Aromatic Compounds................. 2.3.3.3 Epoxidation of Alkenes............................................ 2.3.3.4 Sulfoxidation Reactions............................................ 2.3.3.5 Baeyer-Villiger Reactions......................................... 2.3.3.6 Formation of Hydroperoxides............................................. 2.3.3.7 Dihydroxylation of Aromatic Compounds and Conjugated C=C Bonds............... 2.3.4 Peroxidation Reactions............................................................ 2.4 Formation of Carbon-Carbon Bonds................................................. 2.4.1 Aldol Reactions....................................................................... 2.4.2 Thiamine-Dependent Acyloin and Benzoin Reactions......... 2.5 Addition and Elimination Reactions................................................. 2.5.1 Addition of Water........................................................ 2.5.2 Addition of Ammonia.......................................................... 2.5.3 Cyanohydrin Formation and Henry Reaction........................................... 2.5.4 Michael-Type Additions............................................ 2.6 Transfer Reactions............................................................. 2.6.1 Glycosyl Transfer Reactions.............................................. 2.6.1.1 Glycosyl Transferases........................................ 2.6.1.2 Glycoside phosphorylases and Trans-glycosidases........................................ 2.6.1.3 Glycosidases........................................ 2.6.2 Amino Transfer Reactions................................................... 2.7 Halogenation and Dehalogenation Reactions................................... 2.7.1 Halogenation........................................................................... 2.7.2 Dehalogenation....................................................................... References....................................................................................... 3 Special Techniques 3.1 Enzymes in Organic Solvents.......................................................... 3.1.1 Ester Synthesis........................................................................ 3.1.2 Lactone Synthesis................................................................... 3.1.3 Amide Synthesis..................................................................... 3.1.4 Peptide Synthesis.................................................................... 3.1.5 Peracid Synthesis.................................................................... 3.1.6 Redox Reactions..................................................................... 3.1.7 Medium Engineering............................................................... 3.2 Cascade Reactions............................................................... 3.3 Immobilization.................................................................................. 3.4 Artificial and Modified Enzymes..................................................... 3.4.1 Artificial Enzyme Mimics..................................................... 3.4.2 Modified Enzymes.......................................................... 3.4.2.1 Chemically Modified Enzymes................................ 3.4.2.2 Genetically Modified Enzymes................................ 3.4.3 Catalytic Antibodies................................................................ References........................................................................................ 4 State of the Art and Outlook................................................................. 5 Appendix 5.1 Basic Rules for Handling Biocatalysts.............................................. 5.2 Abbreviations.................................................................................... 5.3 Suppliers of Enzymes....................................................................... 5.4 Commonly Used Enzyme Preparations........................................... 5.5 Major Culture Collections................................................................ 5.6 Pathogenic Bacteria and Fungi........................................................

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