Selective Biocatalysis: A Synthetic Approach

List of Abbreviations 1 Biotransformation and Biocatalysts 1.1 Characteristics of Enzyme Catalyzed Processes 1.1.1 Classification and Nomenclature of Enzymes 1.1.2 Coenzymes 1.1.3 Enzyme Kinetics 1.1.4 Enzyme Immobilization 1.1.5 Effect of Operational Conditions on Enzyme Activity 1.2 Practical Aspects of Transformations Carried Out with Microorganisms 1.2.1 How to Carry Out Microbial Transformations 1.2.2 Immobilized Cells 1.3 Novel Types of Biocatalysts 1.3.1 Biotransformations with Cells of Higher Order Animals and Plants 1.3.2 Artificial Metabolism, Artificial Cells 1.3.3 Modified Enzymes and Cells 1.3.4 Semisynthetic and Fully Synthetic Enzyme Models 1.3.5 Biocatalysis with Biomolecules Other Than Enzymes 2 Stereochemical Aspects of Biocatalysis 2.1 Some Basic Concepts of Stereochemistry 2.2 Determination of Enantiomeric Composition 2.3 Classification of Selective Reactions 2.3.1 Selective Biotransformations: Kinetics and Thermodynamics 2.3.2 Applications of Biocatalysis and Utilization of Various Types of Selectivity 2.3.2.1 Utilization of the Mild Conditions of Biocatalysis 2.3.2.2 Chemoselective Biotransformations 2.3.2.3 Regioselective Biotranformations 2.3.2.4 Diastereomer Selectivity 2.3.2.5 Diastereotope Selectivity 2.3.2.6 Enantiomer Selectivity 2.3.2.7 Enantiotope Selective Biotransformations 2.3.2.8 Biotransformations Involving More Than One Type of Selectivity 3 Hydrolases: Preparative Biocatalysis 3.1 Hydrolases Used for Preparative Purposes 3.1.1 Preparation and Characteristics of Frequently Used Hydrolases 3.2 Biotransformations with Hydrolases: General Considerations 3.2.1 Hydrolysis 3.2.2 Non-Hydrolytic Processes in Organic Solvents 3.3 Biotransformations with Hydrolases: Utilizable Selectivities 3.3.1 Hydrolases: Non-Selective Transformations Under Mild Conditions 3.3.2 Hydrolases: Chemoselectivity - Substrate Specificity 3.3.3 Hydrolases: Regioselectivity 3.3.4 Hydrolases: Diastereomer and Diastereotope Selectivity 3.3.5 Hydrolases: Enantiomer Selectivity 3.3.5.1 Transformations of Amino Acid Derivatives 3.3.5.2 Derivatives of Racemic Acids: Ester Hydrolysis, Alcoholysis, and Esterification 3.3.5.3 Derivatives of Racemic Alcohols: Ester Hydrolysis, Transesterification, Acylation 3.3.5.3 Enantiomer Selectivity with Lactones, Epoxides, Amines and Other Compounds 3.3.6 Hydrolases: Enantiotope Selectivity 3.3.6.1 Transformation of Compounds Containing a Single Prochiral Center 3.3.6.2 Transformation of Meso Compounds 3.3.6.3 Transformation of Enantiotopic and Diastereotopic Faces 4 Oxidoreductases: Preparative Biocatalysis 4.1 Oxidoreductases Not Requiring Added Cofactors 4.2 Oxidoreductases Requiring Added Cofactors 4.2.1 Selective Reactions with Oxidoreductases Requiring Added Cofactors 4.2.1.1 Enantiomer Selectivity: Reduction of Racemic Aldehydes and Oxidation of Racemic Alcohols 4.2.1.2 Enantiotope Selective Reduction of Achiral Carbonyl Compounds 4.2.1.3 Enantiotope Selective Oxidation of Prochiral and Meso-Diols 4.2.1.4 Transformations Involving More Than One Type of Selectivity 5 Baker's yeast 5.1 Reduction of Carbonyl Compounds with Baker's yeast 5.1.1 Reduction of Racemic Aldehydes 5.1.2 Reduction of Ketones 5.1.2.1 Achiral Ketones 5.1.2.2 Racemic Ketones 5.1.3 Reduction of Dioxo Compounds 5.1.3.1 1,2-Dioxo Compounds 5.1.3.2 1,3-Dioxo Compounds 5.1.3.3 Compounds Containing Two Oxo Groups in 1,4 or More Distant Positions 5.1.2 Reduction of Oxocarboxylic Acid Derivatives 5.1.4.1 2-Oxocarboxylic Acid Derivatives 5.1.4.2 3-Oxocarboxylic Acid Derivatives 5.1.4.3 2-Substituted 3-Oxocarboxylic Acid Derivatives 5.1.4.4 Carboxylic Acid Derivatives Containing the Oxo Group in 4 or More Remote Positions 5.2 Reduction of Carbon-Carbon Double Bonds with Baker's yeast 5.3 Other Oxidoreductions with Baker's Yeast 5.4 Hydrolysis with Baker's Yeast 5.5 Exploitation of the Lyase Activity of Baker's Yeast 5.5.1 Acyloin Condensation 5.6 Cyclization Reactions 6 Other Enzymes and Microorganisms 6.1 Isolated Enzymes other than Hydrolases or Oxidoreductases 6.1.1 Enzymes with Transferase Acitivity 6.1.1.1 Enzymes Catalyzing Glycosyl Transfer 6.1.1.2 Aminotransferases 6.1.1.3 Enzymic Phosphorylations 6.1.2 Lyases 6.1.2.1 Aldolases 6.1.2.2 Oxynitrilases 6.2 Microbial Transformations: Selected Examples 6.2.1 Hydrolyric Transformations 6.2.2 Oxidoreductions with Microorganisms Literature Index