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Polyethylene glycol-modified lipase catalyzes asymmetric alcoholysis of δ-decalactone in n-decanol

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Summary

Lipase from Pseudomonas cepacia was modified with 2,4-bis[O-methoxypoly(ethylene glycol)]-6-chloro-s-triazine(activated PEG2) to form PEG-lipase. The PEG-lipase, soluble and active in organic solvents, catalyzes asymmetric alcoholysis of racemic δ-decalactone in alcohols to form (R)-5-hydroxydecanoic acid alkyl esters. The yield was 69% with 83% enantiomeric excess after 3 hr-reaction in n-decanol at 50°C. The advantage of this reaction is that the alcoholysis proceeds efficiently in straight hydrophobic substrates without any organic solvents.

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Authors and Affiliations

  1. Toin Human Science and Technology Center, Department of Materials Science and Technology, Toin University of Yokohama, 1614 Kurogane-cho, Aoba-ku, 225, Yokohama

    Takeshi Uemura, Makoto Furukawa, Yoh Kodera, Misao Hiroto, Ayako Matsushima, Katsukiyo Sakurai & Yuji Inada

  2. Life Science Research Laboratory, Japan Tobacco Inc., 6-2 Umegaoka, Aoba-ku, 227, Yokohama, Japan

    Hideyuki Kuno & Hajime Matsushita

Authors
  1. Takeshi Uemura
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  2. Makoto Furukawa
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  3. Yoh Kodera
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  4. Misao Hiroto
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  5. Ayako Matsushima
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  6. Hideyuki Kuno
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  7. Hajime Matsushita
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  8. Katsukiyo Sakurai
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  9. Yuji Inada
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Uemura, T., Furukawa, M., Kodera, Y. et al. Polyethylene glycol-modified lipase catalyzes asymmetric alcoholysis of δ-decalactone in n-decanol. Biotechnol Lett 17, 61–66 (1995). https://doi.org/10.1007/BF00134197

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  • DOI: https://doi.org/10.1007/BF00134197

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