Skip to main content
Log in

Highly Stereoselective, Uniformly Sized Molecularly Imprinted Polymers for Cinchona Alkaloids in Hydro-Organic Mobile Phases

  • Original Paper
  • Published:
Analytical Sciences Aims and scope Submit manuscript

Abstract

Highly stereoselective, uniformly sized molecularly imprinted polymers (MIPs) for cinchona alkaloids, cinchonine (CN) and cinchonidine (CD), were prepared using methacrylic acid (MAA) as a functional monomer and ethylene glycol dimethacrylate (EDMA) as a cross-linker. The MIPs were evaluated using a mixture of phosphate buffer and acetonitrile as the mobile phase. The CN- and CD-imprinted MAA-co-EDMA polymers can recognize the respective template molecule more than the other diastereomer, and afford an excellent diastereomer separation of CN and CD. In addition, the MIPs gave diastereomer separations of structurally related compounds, quinidine and quinine. The retentive and stereoselective properties of those compounds on the MIPs suggest that electrostatic and hydrophobic interactions can work to recognize these compounds. Furthermore, thermodynamic studies reveal that the entropy-driven effect is significant at mobile-phase pH 5.4, while the enthalpy-driven interactions seem to be dominant at mobile-phase pH 9.6.

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

  1. G. Wulff, Angew. Chem. Int. Ed. Engl., 1995, 34, 1812.

    Article  CAS  Google Scholar 

  2. A. G. Mayes and K. Mosbach, Tre. Anal. Chem., 1997, 16, 321.

    Article  CAS  Google Scholar 

  3. T. Takeuchi and J. Haginaka, J. Chromatogr. B, 1999, 728, 1.

    Article  CAS  Google Scholar 

  4. J. Haginaka, Bioseparation, 2002, 10, 339.

    Google Scholar 

  5. J. Matsui, I. A. Nicholls, and T. Takeuchi, Tetrahedron: Asymmetry, 1996, 7, 1357.

    Article  CAS  Google Scholar 

  6. O. Ramström and R. J. Ansell, Chirality, 1998, 10, 195.

    Article  Google Scholar 

  7. G. Wulff, A. Sarhan, and K. Zabrocki, Tetrahedron Lett., 1973, 14, 4329.

    Article  Google Scholar 

  8. K. Hosoya, K. Yoshizako, N. Tanaka, K. Kimata, T. Araki, and J. Haginaka, Chem. Lett., 1994, 1437.

    Google Scholar 

  9. J. Haginaka and H. Sanbe, Anal. Chem., 2000, 72, 5206.

    Article  CAS  Google Scholar 

  10. J. Haginaka, H. Takehira, K. Hosoya, and N. Tanaka, J. Chromatogr. A, 1998, 816, 113.

    Article  CAS  Google Scholar 

  11. J. Haginaka, H. Sanbe, and H. Takehira, J. Chromatogr. A, 1999, 857, 117.

    Article  CAS  Google Scholar 

  12. J. Haginaka and Y. Sakai, J. Pharm. Biomed. Anal., 2000, 22, 899.

    Article  CAS  Google Scholar 

  13. J. Haginaka and C. Kagawa, J. Chromatogr. A, 2002, 948, 77.

    Article  CAS  Google Scholar 

  14. K. Hosoya and J. M. J. Fréchet, J. Polym. Sci., Part A, Polym. Chem., 1993, 31, 2129.

    Article  CAS  Google Scholar 

  15. K. Hosoya, K. Yoshizako, Y. Shirasu, K. Kimata, T. Araki, N. Tanaka, and J. Haginaka, J. Chromatogr. A, 1996, 728, 139.

    Article  CAS  Google Scholar 

  16. The Merck Index: Thirteenth Edition”, 2001, Merck, Rahway.

  17. B. Sellergren and K. J. Shea, J. Chromatogr. A, 1993, 654, 17.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jun Haginaka.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Haginaka, J., Kagawa, C. Highly Stereoselective, Uniformly Sized Molecularly Imprinted Polymers for Cinchona Alkaloids in Hydro-Organic Mobile Phases. ANAL. SCI. 19, 39–42 (2003). https://doi.org/10.2116/analsci.19.39

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2116/analsci.19.39

Navigation