Abstract
The enantioselectivity for lipase-catalyzed esterifications of 2-(4-substituted phenoxy)propionic acids in organic solvents was found to be mainly controlled by both size (steric) and electronic effects of substituents: H, F, Cl, CF3 and CH3. For the similar substituents in size, CF3 and CH3, however, their electronic effects play an important role in controlling the enantioselectivity. A model for the enantiorecognition is proposed by the discussion based on the value of the Michaelis constant obtained for the enantiomers.
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Ueji, Si., Watanabe, K., Koshiba, T. et al. Lipase-catalyzed esterification of 2-(4-substituted phenoxy)propionic acids in organic solvents: substituent effect controlling enantioselectivity toward racemic acids. Biotechnology Letters 21, 865–868 (1999). https://doi.org/10.1023/A:1005522124925
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DOI: https://doi.org/10.1023/A:1005522124925