@article {Tsai:June 1999:0273-2289:205,
	author = "Tsai, Shau-Wei",
	author = "Tsai, Chin-Shain",
	author = "Chang, Chun-Sheng",
	title = "Lipase-catalyzed synthesis of (S)-naproxen ester prodrug by transesterification in organic solvents",
	journal = "Applied Biochemistry and Biotechnology",
	volume = "80",
	year = "June 1999",
	abstract = "A lipase-catalyzed enantioselective transesterification process was developed for the synthesis of (<I>S</I>)-naproxen 2-<I>N</I>-morpholinoethyl ester prodrug from racemic 2,2,2-trifluoroethyl naproxen ester in organic solvents. By selecting isooctane and 37&#176;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 (<I>S</I>)-ester product were obtained after comparing with the result of an enantioselective esterification process. Studies of water content in isooctane and alcohol containing various <I>N,N</I>-dialkylamino groups on the enzyme activity and enantioselectivity, as well as the recovery of (<I>S</I>)-ester product by using extraction, were also reported.",
	pages = "205-219(15)",
	url = "http://www.ingentaconnect.com/content/hum/abab/1999/00000080/00000003/art00002"
	doi = "doi:10.1385/ABAB:80:3:205"
}