Effects of hydrolysis and esterification side-reactions on the kinetic resolution of enzyme-catalyzed irreversible transesterification in organic solvents

S. W. Tsai*, I. C. Cheng, C. M. Huang

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

11 Scopus citations

Abstract

A simplified kinetic model for the enzyme-catalyzed irreversible transesterification in organic solvents was proposed by considering the hydrolysis and esterification side reactions. The analysis was extended to the kinetic resolution of activated racemic esters containing a chiral center in the acid moiety, and was confirmed from the lipase-catalyzed enantioselective transesterification between (R,S)-suprofen 2,2,2-trifluoroethyl ester and 2-N-morpholinoethanol (or di(ethylene glycol)) in cyclohexane. Theoretical analysis indicates that the time-course yield and/or the enantiomeric excess for the desired (S)-ester product may be improved if the employed enzyme has a higher activity and/or enantioselectivity for the hydrolysis and esterification than the transesterification. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)4571-4582
Number of pages12
JournalChemical Engineering Science
Volume55
Issue number20
DOIs
StatePublished - 10 2000
Externally publishedYes

Keywords

  • Esterification
  • Hydrolysis
  • Irreversible transesterification
  • Kinetic resolution
  • Lipase
  • Suprofen esters

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