Janina E. Kaminska

Preparation of homochiral (S)- and (R)-1-(2-furyl)ethanols by lipase-catalyzed transesterification

Abstract 1-(2-Furyl)ethanol 1 was resolved by irreversible transesterification with vinyl acetate using Lipozyme IM or Porcine Pancreas Lipase (PPL) in an organic solvent. (S)-alcohol (99% e.e.) was obtained in 80–85% yield using Lipozyme IM in carbon tetrachloride while (R)-1-(2-furyl)ethyl acetate (96% e.e.) in 75–80% yield resulted from transesterification using Lipozyme IM in hexane or PPL in tetrahydrofuran.

Kinetic resolution of racemic 2-(2-furyl)-2-hydroxyethyl acetate in the presence of PS lipase

Abstract Kinetic resolution of racemic 2-(2-furyl)-2-hydroxyethyl acetate by transesterification with vinyl acetate in the presence of Amano PS lipase, yielding (1 R )-1-(2-furyl)ethane-1,2-diol diacetate with 98% ee and (2 S )-2-(2-furyl)-2-hydroxyethyl acetate with >99% ee, is described.

Cold-Active Yeast Lipases: Recent Issues and Future Prospects

Microbial lipases are, besides proteases, enzymes of the highest biotechnological potential, catalyzing not only hydrolytic reactions but also – in media of low water activity – synthesis reactions. These enzymes are used in pharmaceutical, food, and household chemicals industries and for the treatment of environmental pollution. Production of lipases is constantly increasing and now accounts for more than one-fifth of the global enzyme market. This review is dedicated to cold-active lipases of yeasts, of which lipases A and B of Pseudozyma (formerly Candida) antarctica have been the most thoroughly investigated. This chapter covers distinctive structural features and specificity of these enzymes in comparison with selected mesophilic lipases as well as modifications (together with diverse immobilization techniques on various supports) directed to improving catalytic properties and stability of these proteins. The application potential of cold-active yeast lipases is discussed; the most important applications include enantio- and regioselective biotransformations, production of biofuels, detergents, food additives, structured triacylglycerols, etc. Some lipases from mesophilic yeasts (e.g., non-conventional yeast Yarrowia lipolytica) show characteristic features of cold-active enzymes, and examples of their use are also considered.