Hydrolysis and Formation of Carboxylic Acid and Alcohol Derivatives

Hydrolases are the enzymes most widely used for organic synthesis. The five most useful and commercially available hydrolases for organic synthesis are the lipases from Candida antarctica, from Candida rugosa and from Burkholderia cepacia, the esterase from pig liver and the protease subtilisin. Hydrolases accept a broad range of substrates, including many typical intermediates in organic synthesis. Beside hydrolysis of carboxylic acid derivatives in water or water-organic solvent mixtures, hydrolases also catalyze the formation of these derivatives in organic solvents. This chapter explains how to plan hydrolase-catalyzed reactions by choosing hydrolases and substrates that are likely to be resolved efficiently and where products are easily separated. Examples include kinetic resolutions (using hydrolysis or acylation), desymmetrizations of prochiral substrates, and dynamic kinetic resolutions.