Enantioselective synthesis of (S)-ibuprofen ester prodrug in cyclohexane by Candida rugosa lipase immobilized on Accurel MP1000.
An enantioselective esterification process was developed for the synthesis of 2-N-morpholinoethyl (S)-ibuprofen ester prodrug from racemic ibuprofen by using Candida rugosa lipase immobilized on Accurel MP1000 in cyclohexane. Compared with the performance of Lipase MY, the immobilized lipase possesses a higher enzyme activity and thermal stability, but with a slightly suppressed enantioselectivity. A kinetic model was proposed and confirmed from experiments, for the simulation of time-course conversions of both enantiomers at various combinations of substrate concentrations in a batch reactor. Preliminary results of employing the proposed model and the immobilized lipase in a continuous packed-bed reactor were also reported and discussed.
Chen
J C
JC
Department of Chemical Engineering, National Cheng Kung University, Tainan 70101, Taiwan, Republic of China.
Tsai
S W
SW
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000737:chemistry; D002175:Candida / Q000201:enzymology*; D003510:Cyclohexanes / Q000737:chemistry*; D004800:Enzymes, Immobilized / Q000737:chemistry*; D004952:Esters; D007052:Ibuprofen / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D008049:Lipase / Q000737:chemistry*; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry; D013379:Substrate Specificity; D013696:Temperature
D000894:Anti-Inflammatory Agents, Non-Steroidal; D003510:Cyclohexanes; D004800:Enzymes, Immobilized; D004952:Esters; D011355:Prodrugs; D008049:Lipase; D007052:Ibuprofen