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A new method for improving the enantioselectivity of lipase-catalyzed hydrolysis in organic solvent containing a small amount of water in the presence of metal ions

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Abstract

The hydrolysis of racemic butyl 2-(4-substituted phenoxy)propionates having various substituents catalyzed by lipase MY from Candida rugosa was achieved in di-isopropyl ether containing 0.75% (v/v) of 2.4 M LiCl or 1.2 M MgCl2 aqueous solution. Water molecules hydrated to the metal ion in isopropyl ether acted as a nucleophile to cause the hydrolysis of these esters as with water alone. Metal ions used significantly enhanced their enantioselectivities by 100-fold or above, as compared with the ordinary reaction media.

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Authors and Affiliations

  1. Graduate School of Science and Technology, Kobe University, Nada, Kobe, 657-8501, Japan

    Takashi Okamoto

  2. Division of Natural Environment and Bioorganic Chemistry, Faculty of Human Development and Sciences, Kobe University, Nada, Kobe, 657-8501, Japan

    Shinichi Ueji

Authors
  1. Takashi Okamoto
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  2. Shinichi Ueji
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Okamoto, T., Ueji, S. A new method for improving the enantioselectivity of lipase-catalyzed hydrolysis in organic solvent containing a small amount of water in the presence of metal ions. Biotechnology Letters 22, 1169–1171 (2000). https://doi.org/10.1023/A:1005637329704

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  • DOI: https://doi.org/10.1023/A:1005637329704

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