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.
Similar content being viewed by others
References
G. Wulff, Angew. Chem. Int. Ed. Engl., 1995, 34, 1812.
A. G. Mayes and K. Mosbach, Tre. Anal. Chem., 1997, 16, 321.
T. Takeuchi and J. Haginaka, J. Chromatogr. B, 1999, 728, 1.
J. Haginaka, Bioseparation, 2002, 10, 339.
J. Matsui, I. A. Nicholls, and T. Takeuchi, Tetrahedron: Asymmetry, 1996, 7, 1357.
O. Ramström and R. J. Ansell, Chirality, 1998, 10, 195.
G. Wulff, A. Sarhan, and K. Zabrocki, Tetrahedron Lett., 1973, 14, 4329.
K. Hosoya, K. Yoshizako, N. Tanaka, K. Kimata, T. Araki, and J. Haginaka, Chem. Lett., 1994, 1437.
J. Haginaka and H. Sanbe, Anal. Chem., 2000, 72, 5206.
J. Haginaka, H. Takehira, K. Hosoya, and N. Tanaka, J. Chromatogr. A, 1998, 816, 113.
J. Haginaka, H. Sanbe, and H. Takehira, J. Chromatogr. A, 1999, 857, 117.
J. Haginaka and Y. Sakai, J. Pharm. Biomed. Anal., 2000, 22, 899.
J. Haginaka and C. Kagawa, J. Chromatogr. A, 2002, 948, 77.
K. Hosoya and J. M. J. Fréchet, J. Polym. Sci., Part A, Polym. Chem., 1993, 31, 2129.
K. Hosoya, K. Yoshizako, Y. Shirasu, K. Kimata, T. Araki, N. Tanaka, and J. Haginaka, J. Chromatogr. A, 1996, 728, 139.
“The Merck Index: Thirteenth Edition”, 2001, Merck, Rahway.
B. Sellergren and K. J. Shea, J. Chromatogr. A, 1993, 654, 17.
Author information
Authors and Affiliations
Corresponding author
Rights 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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2116/analsci.19.39