Abstract
A lipase-catalyzed enantioselective hydrolysis process under continuous in situ racemization of substrate by using trioctylamine as an organic base was developed for the production of (S)-naproxen from racemic naproxen thioesters in isooctane. Naproxen 2,2,2-trifluoroethyl thioester and 45°C were selected as the best substrate and temperature, respectively, by comparing the time-course variations for the racemization of (S)naproxen thioesters containing an electron-withdrawing group. A detailed investigation of the effect of trioctylamine concentration on the kinetic behaviors of the thioester in racemization and enzymatic reaction was conducted, in which more than 70% conversion of the racemate (or 67.2% yield of (S)-naproxen) with ee(p) value higher than 92% was obtained.
Original language | English |
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Pages (from-to) | 120-126 |
Number of pages | 7 |
Journal | Biotechnology and Bioengineering |
Volume | 64 |
Issue number | 1 |
DOIs | |
State | Published - 05 07 1999 |
Externally published | Yes |
Keywords
- Dynamic resolution
- Enantioselective hydrolysis
- Lipase
- Naproxen thioesters