Lipases: useful biocatalysts for enantioselective reactions of chiral flavor compounds
1992
Engel, K.H.
A commercially available lipase preparation from Candida cylindracea (CCL) has been employed for kinetic resolutions of the enantiomers of chiral acids and their esters. CCL-catalyzed esterification of 2-methylalkanoic acids and transesterification of the corresponding esters via acidolysis proceed with a preference for the (S)-configurated substrates. Structural influences on velocity and enantioselectivity of these reactions are demonstrated. Limitations of the acidolysis due to the reversibility of the reaction are discussed. Lipase-catalyzed reactions of hydroxyacid esters with fatty acids in organic solvent are characterized by a competition of esterification and transesterification. The rates of these pathways and their stereochemical course depend on the position of the hydroxy group and determine the final distribution of products.
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