Lipase-catalyzed dynamic resolution of naproxen 2,2,2-trifluoroethyl thioester by hydrolysis in isooctane

Chun Sheng Chang, Shau Wei Tsai*, Jimmy Kuo

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

43 Scopus citations

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 languageEnglish
Pages (from-to)120-126
Number of pages7
JournalBiotechnology and Bioengineering
Volume64
Issue number1
DOIs
StatePublished - 05 07 1999
Externally publishedYes

Keywords

  • Dynamic resolution
  • Enantioselective hydrolysis
  • Lipase
  • Naproxen thioesters

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