Enantioselective esterification of racemic naproxen by lipases in organic solvent.

S W Tsai, H J Wei

Index: Enzyme Microb. Technol. 16(4) , 328-33, (1994)

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Abstract

Enantioselective esterification of naproxen, 2-(6-methoxy-2-naphthyl) propionic acid, was attempted by lipases in nearly anhydrous isooctane. The nature of the alcohol affects the reactivity and enantioselectivity of the lipase from Candida cylindracea. Alcohols containing a trimethylsilyl group are highly reactive and enantioselective to the S-isomer of the acid. An optimal temperature around 65 degrees C and an enzyme concentration less than 7 mg ml-1 were proposed to resolve the racemate, with trimethylsilyl methanol as nucleophile, from a consideration of the enantiomeric ratio, the ester formation, and the resistance of mass transfer for the substrate.