Metal ions dramatically enhance the enantioselectivity for lipase-catalysed reactions in organic solvents

Takashi Okamoto, Ebara Yasuhito, Shin Ichi Ueji

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

We propose a simple and a powerful method to enhance the enantioselectivity for lipase-catalysed transformations in organic solvents by an addition of metal ion-containing water to the reaction mixture. In this paper, various metal ions such as LiCl or MgCl2 are tested to improve the enantioselectivity for the model reactions. The enantioselectivities obtained are dramatically enhanced, the E values of which are about 100-fold as compared with the ordinary conditions without a metal ion, for example, E = 200 by addition of LiCl. Furthermore, lowering the reaction temperature led to an almost perfect enantioselectivity of lipase in the presence of a metal ion, for example, E = 1300 by addition of LiCl. Also, a mechanism for the drastic enhancement by metal ions is discussed briefly on the basis of the EPR spectroscopic study and the initial rate for each enantiomer of the substrate.

Original languageEnglish
Pages (from-to)1147-1153
Number of pages7
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number6
DOIs
Publication statusPublished - 2006
Externally publishedYes

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Enantioselectivity
Lipase
Organic solvents
Metal ions
metal ions
Metals
Ions
Magnesium Chloride
Enantiomers
enantiomers
Paramagnetic resonance
Temperature
Water
augmentation
Substrates
water
temperature

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Chemistry(all)

Cite this

Metal ions dramatically enhance the enantioselectivity for lipase-catalysed reactions in organic solvents. / Okamoto, Takashi; Yasuhito, Ebara; Ueji, Shin Ichi.

In: Organic and Biomolecular Chemistry, Vol. 4, No. 6, 2006, p. 1147-1153.

Research output: Contribution to journalArticle

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