Skip to main content
Log in

Effects of water content on the enantioselectivity of α-chymotrypsin catalysis in organic media

  • Published:
Biotechnology Letters Aims and scope Submit manuscript

Summary

The α-chymotrypsin-catalyzed transesterification between N-trifluoroacetyl-DL-phenylalanine trifluoroethyl ester and 1-propanol was carried out in a variety of organic solvents. The addition of small quantities of water enhanced both the rate of reaction and enantioselectivity. A high enantioselectivity was achieved in ethyl acetate (E = 120), diethyl ether (86), or acetonitrile (60). The competing hydrolysis became significant at water content higher than 0.5% (w/w).

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

Access this article

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

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

    Google Scholar 

  • Chen, C.-S., Wu, S.-H., Girdaukas, G. and Sih, C.J. (1987). J. Am. Chem. Soc. 109, 2812–2817.

    Google Scholar 

  • Chen, C.-S. and Sih, C.J. (1989). Angew. Chem. Int. Ed. Engl. 28, 695–707.

    Google Scholar 

  • Clapés, P., Adlercreutz, P. and Mattiason, B. (1990). J. Biotechnol. 15, 323–338.

    Google Scholar 

  • Dordick, J.S. (1989). Enzyme Microb. Technol. 11, 194–211.

    Google Scholar 

  • Fitzpatrick, P.A. and Klibanov, A.M. (1991). J. Am. Chem. Soc. 113, 3166–3171.

    Google Scholar 

  • Kise, H., Hayakawa, A., Noritomi, H. (1990). J. Biotechnol. 14, 239–254.

    Google Scholar 

  • Kise, H. and Tomiuchi, Y. (1991). Biotechnol. Lett. 13, 317–322.

    Google Scholar 

  • Kitaguchi, H., Itoh, I. and Ono, M. (dy1990). Chem. Lett. 1203–1206.

  • Klibanov, A.M. (1990). Acc. Chem. Res. 23, 114–120.

    Google Scholar 

  • Laane, C., Boeren, S., Vos, K. and Veeger, C. (1987). Biotechnol. Bioeng. 30, 81–87.

    Google Scholar 

  • Laitinen, H.A. and Harris, W.E. (1975). Chemical Analysis, 2nd ed.; MacGraw-Hill: New York, pp. 361–363.

    Google Scholar 

  • Margolin, A.L., Tai, D.F. and Klibanov, A.M. (1987). J. Am. Chem. Soc. 109, 7885–7887.

    Google Scholar 

  • Miyazawa, T., Mio, M., Watanabe, Y., Yamada, T. and Kuwata, S. (1992). Biotechnol. Lett. 14, 789–794.

    Google Scholar 

  • Reichardt, C. (1988). Solvents and Solvent Effects in Organic Chemistry, 2nd ed.; VCH: Weinheim, Germany, pp. 408–410.

    Google Scholar 

  • Sakurai, T., Margolin, A.L. Russell, A.J. and Klibanov, A.M. (1988). J. Am. Chem. Soc. 110, 7236–7237.

    Google Scholar 

  • Secundo, F., Riva, S. and Carrea, G. (1992). Tetrahedron Asymmetry 3, 267–280.

    Google Scholar 

  • Sinisterra, J.V., Llama, E.F., Campo, C., Cabezas, M.J., Moreno, J.M. and Arroyo, M. (1994). J. Chem. Soc. Perkin Trans., 2, 1333–1336.

    Google Scholar 

  • Stokes, T.M. and Oehlschlager, A.C. (1987). Tetrahedron Lett. 28, 2091–2094.

    Google Scholar 

  • Tawaki, S. and Klibanov, A.M. (1992). J. Am. Chem. Soc. 114, 1882–1884.

    Google Scholar 

  • Tomiuchi, Y., Ohshima, K. and Kise, H. (1992). Bull. Chem. Soc. Jpn., 65, 2599–2603.

    Google Scholar 

  • Zaks, A. and Klibanov, A. M. (1985). Proc. Natl. Acad. Sci. USA 82, 3192–3196.

    Google Scholar 

  • Zaks, A. and Klibanov, A. M. (1988a). J. Biol. Chem. 263, 3194–3201.

    Google Scholar 

  • Zaks, A. and Klibanov, A. M. (1988b). J. Biol. Chem. 263, 8017–8021.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kawashiro, K., Sugahara, H., Sugiyama, S. et al. Effects of water content on the enantioselectivity of α-chymotrypsin catalysis in organic media. Biotechnol Lett 17, 1161–1166 (1995). https://doi.org/10.1007/BF00128378

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00128378

Keywords

Navigation