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

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Date: June 1999
From: Applied Biochemistry and Biotechnology(Vol. 80, Issue 3)
Publisher: Springer
Document Type: Article
Length: 166 words

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Abstract :

Byline: Shau-Wei Tsai (1), Chin-Shain Tsai (1), Chun-Sheng Chang (1) Keywords: Lipase; enantioselective transesterification; (S)-naproxen ester prodrugs 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 37degC 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. Author Affiliation: (1) Department of Chemical Engineering, National Cheng Kung University, 70101, Tainan Taiwan, Republic of China Article History: Registration Date: 09/05/1999 Received Date: 13/08/1998 Accepted Date: 03/12/1998

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Gale Document Number: GALE|A203366251