IngentaConnect Lipase-catalyzed synthesis of (S)-naproxen ester prodrug by trans...

Authors: Tsai, Shau-Wei¹; Tsai, Chin-Shain²; Chang, Chun-Sheng²

Source: Applied Biochemistry and Biotechnology, Volume 80, Number 3, June 1999 , pp. 205-219(15)

Abstract:

A lipase-catalyzed enantioselective transesterification process was developed for the synthesis of (S)-naproxen 2-N-morpholinoethyl ester prodrug from racemic 2,2,2-trifluoroethyl naproxen ester in organic solvents. By selecting isooctane and 37°C as the best solvent and temperature, the apparent fits of the initial conversion rates for transesterification and hydrolysis side reaction suggest a ping-pong Bi-Bi enzymatic mechanism with the alcohol as a competitive enzyme inhibitor. Improvements in the initial conversion rate and the productivity for the desired (S)-ester product were obtained after comparing with the result of an enantioselective esterification process. Studies of water content in isooctane and alcohol containing various N,N-dialkylamino groups on the enzyme activity and enantioselectivity, as well as the recovery of (S)-ester product by using extraction, were also reported.

Keywords: Lipase; enantioselective transesterification; (S)-naproxen ester prodrugs

Document Type: Research article

DOI: 10.1385/ABAB:80:3:205

Affiliations: 1: Department of Chemical Engineering, National Cheng Kung University, 70101, Tainan Taiwan, Republic of China, Email: t62647@mail.ncku.edu.tw 2: Department of Chemical Engineering, National Cheng Kung University, 70101, Tainan Taiwan, Republic of China,

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Lipase-catalyzed synthesis of (S)-naproxen ester prodrug by transesterification in organic solvents