Poly(ethylene glycol)-lipase complexes that are highly active and enantioselective in ionic liquids

Tatsuo Maruyama, Hiroshi Yamamura, Takahiro Kotani, Noriho Kamiya, Masahiro Goto

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

Lipase-catalyzed alcoholysis between vinyl acetate and 2-phenyl-1-propanol was investigated in dialkylimidazolium-based ionic liquids. Although native lipase powder exhibited very low activity in an ionic liquid, forming a polyethylene glycol) (PEG)-lipase complex improved the lipase activity in the ionic liquid. The activity of the PEG-lipase complex was higher in ionic liquids than in common organic solvents (n-hexane, isooctane and dimethylsulfoxide). Fluorescence measurements using 4-aminophthalimide revealed that the ionic liquids were more hydrophilic than the organic solvents used for non-aqueous enzymology. A kinetic study of lipase-catalyzed alcoholysis in an ionic liquid ([Bmim][PF6]) revealed that the Michaelis constant (Km) for 2-phenyl-1-propanol in the ionic liquid was half that in n-hexane, suggesting that the ionic liquid stabilized the enzyme-substrate complex. Finally, we carried out enantioselective alcoholysis of 1-phenylethanol in ionic liquids employing the PEG-lipase complex, and obtained high enantioselectivity, comparable to that in n-hexane.

Original languageEnglish
Pages (from-to)1239-1244
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number8
DOIs
Publication statusPublished - Apr 21 2004

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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