Enantioselective hydrolysis of (R,S)-naproxen 2,2,2-trifluoroethyl ester in water-saturated solvents via lipases from Carica pentagona Heilborn and Carica papaya

Chun Chi Chen, Shau Wei Tsai*, Pierre Villeneuve

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

22 Scopus citations

Abstract

A crude lipase prepared from Carica pentagona Heilborn latex was explored as an effective enantioselective biocatalyst for the hydrolytic resolution of (R,S)-naproxen 2,2,2-trifluoroethyl ester in water-saturated organic solvents. Comparisons of the enzyme performance with that from Carica papaya lipase indicated that both lipases showed low tolerance to the hydrophilic solvent and were inhibited by (S)-naproxen and 2,2,2-trifluoroethanol. Improvements on the enzyme activity and enantioselectivty were demonstrated when both lipases in partially purified forms were employed. By using the thermodynamic analysis, the enantiomeric discrimination was mainly driven by the difference of activation enthalpy for all reaction systems except for employing Carica papaya lipase as the biocatalyst for (R,S)-fenoprofen 2,2,2-trifluoroethyl thioester.

Original languageEnglish
Pages (from-to)51-57
Number of pages7
JournalJournal of Molecular Catalysis B: Enzymatic
Volume34
Issue number1-6
DOIs
StatePublished - 01 07 2005
Externally publishedYes

Keywords

  • (S)-Naproxen
  • Carica papaya
  • Carica pentagona Heilborn
  • Hydrolytic resolution
  • Lipases

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