Lipase-catalyzed enantioselective esterification of (S)-naproxen hydroxyalkyl ester in organic media.
A lipase-catalyzed, enantioselective esterification process in organic solvents was developed for the synthesis of (S)-naproxen hydroxyalkyl ester. With the selection of lipase (Candida rugosa lipase) and reaction medium (isooctane and cyclohexane), a high enantiomeric ratio of > 100 for the enzyme was obtained. 1,4-Butanediol was the best acyl acceptor. The carbon chain length of the alcohol had a major effect on the enzyme activity and enantioselectivity of lipase-catalyzed esterification.
Chang
Chun-Sheng
CS
Department of Biotechnology, Southern Taiwan University of Technology, Tainan Hsien, Taiwan 710. cs_chang@mail.stut.edu.tw
Hsu
Chin-Shuo
CS
Shang
Chun-Sheng
CS
D000438:Alcohols / Q000737:chemistry; D002175:Candida / Q000737:chemistry / Q000201:enzymology; D004951:Esterification; D008049:Lipase / Q000737:chemistry* / Q000145:classification; D009288:Naproxen / Q000138:chemical synthesis* / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis; D012997:Solvents / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D011355:Prodrugs; D012997:Solvents; D009288:Naproxen; D008049:Lipase