Biocatalysis

Biotransformations and biocatalysis

Characteristic advantages and disadvantages of processes – Enzyme classification and nomenclature – Coenzymes – Enzyme kinetics – Protein structure and basics of enzyme action – Effect of conditions on enzyme activity – Characteristics of microbial transformations – Enzyme- and cell immobilization

Development of novel biocatalysts

Genetic engineering tools – Production of biocatalysts by recombinant organisms – Novel methods of modifications of enzyme properties by genetic methods: site directed mutagenesis, gene shuffling, directed evolution, metabolic engineering, random DNA cloning – Catalytic antibodies – High throughput test methods

Stereochemical issues related to biocatalytic processes

Basic terms of stereochemistry – Methods to determine enantiomeric composition – Classification of selective transformations

Types of selectivities for biocatalytic processes

Mild conditions – Chemoselectivity – Regioselectivity – Diastereomer selectivity – Diastereotopic selectivity – Enantiomer selectivity – Enantiotopic selectivity – Parallel manifestation of multiple selectivities

Hydrolases

General features of processes performed by hydrolases

Characteristics of hydrolases used for preparative purposes – General features of transformations by hydrolases: hydrolytic processes in aqueous media – non-hydrolytic processes in organic solvents

Preparative application of hydrolases: types of the applicable selectivities

Biotransformations under mild conditions – Substrate specificity, chemoselectivity – Regioselective transformations – Diastereomer and diastereotopic selective processes – Enantiomer selective biotransformations: general considerations, transformations of amino acids and their derivatives, selective transformations of racemic acids (ester hydrolysis, alcoholysis, transesterification), selective transformations of racemic alcohols (ester hydrolysis, acylation, transesterification), racemic lactones, amines, epoxides and other compounds – Enantiotopic selective biotransformations: general considerations, transformations of compounds with a single prochiral center, reactions of meso compounds, enantiotopic and diastereotopic face distinctions by hydrolases

Oxidoreductases

General features of processes by oxidoreductases

Features of oxidoreductases applied for preparative purposes – Processes by oxidoreductases acting without external cofactor – General features of oxidoreductases acting with externally added cofactors – Cofactor regeneration methods by using oxidoreductases

Preparative use of oxidoreductases: types of useful selectivities

Reduction of racemic aldehydes – Oxidation of racemic alcohols – Reduction of achiral carbonyl compounds – Oxidation of prochiral and meso alcohols – Simultaneous manifestation of multiple selectivities in processes with oxidoreductases – Enzymatic Baeyer-Villiger-type oxidations

Baker's yeast as whole-cell system for preparative use

General considerations – Reduction of ketones: achiral ketones, racemic ketones, 1,2-dioxo compounds, 1,3-dioxo compounds, other dioxo compounds – Reduction of oxocarboxylic acid derivatives: 2-oxocarboylic acid derivatives, 3-oxocarboylic acid derivatives, 2-substituted-3-oxocarboylic acid derivatives, oxocarboxylic acid derivatives with carbonyl function at 4 or more distant position – Reduction of carbon-carbon double bond – Other reductions – Hydrolysis – Lyase activity – Cyclizations

Other preparative application of enzymes and microorganisms

Other enzymes: transferases (glycosidases, aminotransferases, phosphorylases) – Lyases (aldolases, oxynitrilases) – Selected examples of whole-cell biotransformations

Industrial applications of biotransformation

Enzyme and cell immobilization – Bioreactors – Stereoselective biotransformations carried out on an industrial scale