Biotransformations in Organic Chemistry: A Textbook

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.................................