Skip to main content
SpringerLink
Log in

Production of (2R,3S)-3-(4-methoxyphenyl)glycidic acid methyl ester using an emulsion bioreactor containing lipase fromSerratia marcescens

  • Original Articles
  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

An emulsion bioreactor for production of (2R,3S)-3-(4-methoxyphenyl) glycidic acid methyl ester ([-]MPGM) from a racemic mixture ([±]MPGM) using the lipase fromSerratia marcescens has been proposed. Kinetics of hydrolyzing reaction and purification of (-)MPGM from the reaction mixture were investigated to provide a basis for industrial application of this bioreactor. The hydrolyzing reaction in the bioreactor proceeded at a rate that was first order in substrate concentration. The reaction rate was affected by a stirring speed and the ratio of the aqueous phase containing lipase to the toluene phase containing substrate. Phase separation after the enzymatic reaction was accomplished by addition of surfactant to the reaction mixture, and crystalline (-)MPGM with a chemical purity of 100% and optical purity of 100% enantiomeric excess was obtained in a high yield of 40–43% by concentration of the toluene solution.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Matsumae, H., Furui, M., and Shibatani, T. (1993),J. Ferment. Bioeng. 75, 93–98.

    Article  CAS  Google Scholar 

  2. Matsumae, H., Furui, M., Shibatani, T., and Tosa, T. (1994),J. Ferment. Bioeng. 78, 59–63.

    Article  CAS  Google Scholar 

  3. Chen, C. S., Fujimoto, Y., Gridaukas, G., and Sih, C. J. (1982),J. Am. Chem. Soc. 104, 7294–7299.

    Article  CAS  Google Scholar 

  4. Mitsuda, S., Nabeshima, S., and Hirohara, H. (1989),Appl. Microbiol. Biotechnol. 31, 334–337.

    Article  CAS  Google Scholar 

  5. Sasaki, T. (1967),Kagaku-Kogaku 31, 432–437.

    Google Scholar 

  6. Goto, M., Me, J., Kondo, K., and Nakashio, F. (1989),J. Chem. Eng. Japan 22, 401–406.

    Article  CAS  Google Scholar 

  7. Goto, M. (1991),Kagaku-Kogaku 55, 420–422.

    CAS  Google Scholar 

  8. Kato, S. (1992),Hyomen 30, 119–125.

    CAS  Google Scholar 

  9. Osasa, K., Hideo, N., and Sambuichi, M. (1992),Kagaku-Kogaku Ronbunshu 18, 433–440.

    CAS  Google Scholar 

  10. Pine, S. H., Hendrickson, J. B., Cram, D. J., and Hammond, D. (1981),Organic Chemistry, 4th ed., McGraw-Hill, New York, pp. 256–257.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Production Technology Division, Tanabe Seiyaku Co., Ltd., 16-89, Kashima-3-chome, Yodogawa-ku, 532, Osaka, Japan

    Toshiyuki Furutani, Masakatsu Furui & Takao Mori

  2. Research Laboratory of Applied Biochemistry, Tanabe Seiyaku Co., Ltd., 16-89, Kashima-3-chome, Yodogawa-ku, 532, Osaka, Japan

    Takeji Shibatani

Authors
  1. Toshiyuki Furutani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Masakatsu Furui
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Takao Mori
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Takeji Shibatani
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Furutani, T., Furui, M., Mori, T. et al. Production of (2R,3S)-3-(4-methoxyphenyl)glycidic acid methyl ester using an emulsion bioreactor containing lipase fromSerratia marcescens . Appl Biochem Biotechnol 59, 319–328 (1996). https://doi.org/10.1007/BF02783573

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02783573

Index Entries

Search

Navigation