Molecular modeling and experimental verification of lipase-catalyzed enantioselective esterification of racemic naproxen in supercritical carbon dioxide

Cheong Hoon Kwon, Jeong Yeong Jeong, Jeong Won Kang

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

Experimental and simulation analyses were performed on the lipase-catalyzed esterification reaction of racemic naproxen by CALB (candida antarctica lipase B) enzyme in supercritical carbon dioxide. The reaction pathways were investigated by quantum mechanical analysis, and the enantioselectivity of the products was predicted by molecular dynamics simulation analysis. Calculated results from molecular modeling in supercritical carbon dioxide were qualitatively compared with experimental data by using racemic naproxen as a substrate. All molecular modeling results and experimental data were acquired and compared with those in ambient and supercritical condition. Moreover, to verify the stability of enzymatic reaction in each solvent condition, reaction pathways were investigated in several solvent conditions (vacuum, water, hexane and supercritical carbon dioxide), and the stability of enzymatic reaction in supercritical carbon dioxide was compared with other solvent conditions.

Original languageEnglish
Pages (from-to)214-219
Number of pages6
JournalKorean Journal of Chemical Engineering
Volume26
Issue number1
DOIs
Publication statusPublished - 2009 Jan

Keywords

  • Candida antarctica lipase B
  • Enantioselectivity
  • Molecular dynamics simulation
  • Quantum mechanical analysis
  • Racemic naproxen
  • Supercritical carbon dioxide

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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