Stereospecific Hydrolysis of 2-Oxazolidinone Esters and Separation of Products with an Immobilized Lipase Column

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Hydrophobic (R, S)-5-acyloxymethyl-3-alkyl-2-oxazolidinones were successfully hydrolyzed stereospecifically with lipoprotein lipase Amano 3 (LPL) adsorbed on Amberlite XAD-7. The LPL immobilized on the resin was not desorbed on washing with phosphate buffer, toluene or hexane. The activity loss of the column was little during storage for five months at room temperature. Stereospecific hydrolyses were performed pulsewise with the column, and separation of the hydrophobic (S)-ester from the hydrophilic (R)-alcohol was also performed on the same column utilizing the hydrophobic interaction between the (S)-ester and the support resin. The immobilized LPL column was stable on repetition of these operations for over 20 times. The optical purities of the obtained (S)-oxazolidinones, which were favorable intermediates for the synthesis of (S)-β-blockers, were 96-98% e.e.
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