Tetrahedron Asymmetry p. 2749 - 2755 (1997)
Update date:2022-08-29
Topics:
Effenberger, Franz
Graef, Bernd Walter
Osswald, Steffen
Racemic naproxen amide (RS)-1 was hydrolyzed to enantiomerically pure naproxen (S)-2 in water-saturated organic solvents with log P values between 2.0 and 0.17 using immobilized resting cells of the bacterial strain Rhodococcus erythropolis MP50. Alkyl acetates are the most suitable solvents concerning solubility of (RS)-1 and enzyme activity. In butyl acetate with 3 vol% DMSO as cosolvent and an increased water content of the immobilized cells the rate of hydrolysis was an optimum. Under these reaction conditions a preparative scale application gave after 45 h, at a conversion rate of 48%, (S)-2 with >99% ee and an isolated yield of 84%.
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