Jacek Dulęba, Tomasz Siódmiak, Rafał Mastalerz, Natalia Kocot, Agnieszka Dębińska, Emilia Suchomska, Mateusz Czeczka, Kamil Cała, Dorota Wątróbska-Świetlikowska, Michał Piotr Marszałł
The application of lipase from Burkholderia cepacia in the enantioselective pharmaceutical biocatalysis 9
Lipases are widely applied catalysts in the pharmaceutical and biotechnological industries. They are characterized by high catalytic activity, and stability and are environmentally friendly. These enzymes could be used in free and in immobilized form. The immobilization procedure is exerted to improve enzyme activity and is carried out by different methods (e.g. physical adsorption, covalent binding, ionic interaction, encapsulation, cross-linking, entrapment). The most important lipase activities are enantioselectivity (e.g. the kinetic resolution of the racemic mixture) and lipolytic activity, enabling hydrolysis of triacylglycerol (TAG) to free fatty acids (FFA) and glycerol in an aqueous medium. One of the most commonly investigated is lipase from Burkholderia cepacia (BCL), characterized by high hydrolytic activity, regardless of the length of the organic acid chain. The enantioselectivity of BCL allows receiving chirally pure compounds in, among others, the transesterification reactions.
The review aimed to present the application of BCL in enantioselective reactions of pharmaceutical significance. Obtained using this lipase, the (R)-1-phenylethanol, is the chiral building block in drug synthesis. However, BCL has been also studied for the synthesis of nonsteroidal anti-inflammatory drugs (NSAIDs) such as (S)-ibuprofen and (S)-ketoprofen. Moreover, this enzyme has been used in the kinetic resolution of myo-inositol derivatives, applied in treating hormonal disorders, and (R,S)-mandelic acid used in dermatology. It was shown that BCL was also helpful in receiving chirally pure L-menthol, the demulcent and cooling compound in various drug forms. The application of BCL in catalyzing desymmetrization of propan-1,3-diol derivatives, applied as intermediates in various drug synthesis, has been noted. Therefore, BCL seems to be one of the most suitable catalysts for performing pharmaceutical biocatalysis and is of increasing interest to researchers and research consortia.
Keywords: lipase from Burkholderia cepacia, immobilization, enantioselectivity, chiral drugs, chiral intermediates.
© Farm Pol, 2022, 78(4): 194–200