Macromolecular Research

The Polymer Society of Korea (한국고분자학회)
권호 표지

Efficient Immobilization of Polysaccharide Derivatives as Chiral Stationary Phases via Copolymerization with Vinyl Monomers

  • Chen, Xiaoming (EcoTopia Science Institute, Nagoya University) ;
  • Okamoto, Yoshio (EcoTopia Science Institute, Nagoya University) ;
  • Yamamoto, Chiyo (Department of Applied Chemistry, Graduate School of Engineering, Nagoya University)
  • Published : 2007.03.31
Download PDF
⟨ Previous Next ⟩

Abstract

The direct chromatographic separation of enantiomers by chiral stationary phases (CSPs) has been extensively developed over the past two decades, and has now become the most popular method for the analytical and preparative separations of enantiomers. Polysaccharide derivatives coated onto silica gel, as CSPs, playa significantly important role in the enantioseparations of a wide range of chiral compounds using high-performance liquid chromatography (HPLC). Unfortunately, the strict solvent limitation of the mobile phases is the main defect in the method developments of these types of coated CSPs. Therefore, the immobilization of polysaccharide derivatives onto silica gel, via chemical bonding, to obtain a new generation of CSPs compatible with the universal solvents used in HPLC is increasingly important. In this article, our recent studies on the immobilization of polysaccharide derivatives onto the silica gel, as CSPs, through radical copolymerization with various vinyl monomers are reported. Polysaccharide derivatives, with low vinyl content, can be efficiently fixed onto silica gel with high chiral recognition.

Keywords

References

  1. N. M. Maier, P. Franco, and W. Linder, J. Chromatogr. A, 906, 3 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  2. V. Schurig, J. Chromatogr. A, 906, 275 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  3. V. Schurig, Trends Anal. Chem., 21, 647 (2002)
  4. D. W. Armstrong, LC.GC Int., 11, 22 (1998)
  5. E. Yashima, C. Yamamoto, and Y. Okamoto, Synlett, 344 (1998)
  6. Y. Okamoto and E. Yashima, Angew. Chem. Int. Ed., 37, 1021 (1998)
  7. E. Yashima, J. Chromatogr. A, 906, 105 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  8. K.W. Phinney, Anal. Chem., 72, 204A (2000)
  9. G. Terfloth, J. Chromatogr. A, 906, 301 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  10. J. Kang, D. Wistuba, and V. Schurig, Electrophoresis, 23, 4005 (2002)
  11. J. Haginaka, J. Chromatogr. A, 906, 253 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  12. Z. Juvancz and J. Szejtli, Trends Anal. Chem., 21, 379, (2002)
  13. G. Felix, J. Chromatogr. A, 906, 171 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  14. K. Tachibana and A. Ohnishi, J. Chromatogr. A, 906, 127 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  15. H. Y. Aboul-Enein, J. Chromatogr. A, 906, 185 (2001)
  16. C. Yamamoto and Y. Okamoto, Bull. Chem. Soc. Jpn., 77, 227 (2004) https://doi.org/10.1246/bcsj.77.227
  17. J. W. Timothy and B. F. Alton III, J. Chromatogr. A, 906, 73 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  18. F. Gasparrini, D. Misiti, and C. Villani, J. Chromatogr. A, 906, 35 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  19. E. Francotte, in The Impact of Stereochemistry on Drug Development and Use, H. Y. Aboul-Enein and I. W. Wainer, Eds., Wiley, New York, 1997, chap. 23, pp. 633-683
  20. Y. Okamoto, M. Kawashima, and K. Hatada, J. Am. Chem. Soc.,106, 5357 (1984) https://doi.org/10.1021/ja00316a028
  21. Y. Okamoto, M. Kawashima, and K. Hatada, J. Chromatogr., 363, 173 (1986)
  22. Y. Okamoto, R. Aburatani, S. Miura, and K. Hatada, J. Liq. Chromatogr., 10, 1613 (1987) https://doi.org/10.1080/01483918708066791
  23. E. Yashima, H. Fukaya, and Y. Okamoto, J. Chromatogr. A, 667, 11 (1994)
  24. K. Kimata, R. Tsuboi, K. Hosoya, and N. Tanaka, Anal. Methods Instrum., 1, 23 (1993)
  25. C. Minguillón, P. Franco, L. Oliveros, and P. Lopez, J. Chromatogr. A, 728, 407 (1996)
  26. P. Franco, C. Minguillón, L. Oliveros, and P. Lopez, J. Chromatogr. A, 791, 37 (1997)
  27. P. Franco, A. Senso, C. Minguillón, and L. Oliveros, J. Chromatogr. A, 796, 265 (1998)
  28. X. Chen, F. Qin, Y. Liu, X. Huang, and H. Zou, J. Chromatogr. A, 1034, 109 (2004)
  29. E. Francotte, PCT WO Patent 96/27615 (1996)
  30. E. Francotte and T. Zhang, PCT WO Patent 97/044011 (1997)
  31. E. Francotte, PCT WO Patent 97/49733 (1997)
  32. E. Francotte, and D. Huynh, J. Pharm. Biomed. Anal., 27, 421 (2002)
  33. N. Enomoto, S. Furukawa, Y. Ogasawara, H. Akano, Y. Kawamura, E. Yashima, and Y. Okamoto, Anal. Chem., 68, 2798 (1996)
  34. X. Chen, Y. Liu, F. Qin, L. Kong, and H. Zou, J. Chromatogr. A, 1010, 185 (2003)
  35. B. Chankvetadze, T. Ikai, C. Yamamoto, and Y. Okamoto, J. Chromatogr. A, 1042, 55 (2004)
  36. T. Ikai, R. Muraki, C. Yamamoto, M. Kamigaito, and Y. Okamoto, Chem. Lett., 33, 1188 (2004) https://doi.org/10.1246/cl.2004.1188
  37. P. Franco, A. Senso, L.Oliveros, and C. Minguillon, J. Chromatogr. A, 906, 155 (2001) https://doi.org/10.1016/S0021-9673(00)01123-7
  38. T. Ikai, C. Yamamoto, M. Kamigaito, and Y. Okamoto, Polym. J., 38, 91 (2006) https://doi.org/10.1295/polymj.38.91
  39. T. Kubota, T. Kusano, C. Yamamoto, E. Yashima, and Y. Okamoto, Chem. Lett., 7, 724 (2001)
  40. T. Kubota, C. Yamamoto, and Y. Okamoto, Chirality, 15, 77 (2003) https://doi.org/10.1002/chir.10175
  41. T. Kubota, C. Yamamoto, and Y. Okamoto, J. Polym. Sci.; Part A: Polym. Chem., 41, 3703 (2003)
  42. T. Kubota, C. Yamamoto, and Y. Okamoto, J. Polym. Sci.; Part A: Polym. Chem., 42, 4704 (2004)
  43. X. Chen, C. Yamamoto, and Y. Okamoto, J. Chromatogr. A, 1104, 62 (2006)
  44. X. Chen, C. Yamamoto, and Y. Okamoto, J. Sep. Sci., 29, 1432 (2006)
  45. T. E. Wood, A. C. Ross. N. D. Dalgleish, E. D. Power, A. Thompson, X. Chen, and Y. Okamoto, J. Org. Chem., 70, 9967 (2005)
  46. M. R. Kishan, A. Parham, F. Schelhase, A. Yoneva, G. Silva, X. Chen, Y. Okamoto, and F. Vögtle, Angew. Chem. Int. Ed., 45, 7296 (2007) https://doi.org/10.1002/anie.200690003
  47. A. Bohmer, J. Brüggemann, A. Kaufmann, A. Yoneva, S. Muler, W. M. Müller, U. Muler, F. W. Vergeer, L. F. Chi, L. DeCola, H. Fuchs, X. Chen, T. Kubota, Y. Okamoto, and F. Vogtle, Eur. J. Org. Chem., 1, 45 (2007)
  48. T. Zhang, C. Kientzy, P. Franco, A. Ohnishi, Y. Kagamihara, and H. Kurosawa, J. Chromatogr. A, 1075, 65 (2005)
  49. T. Zhang, D. Nguyen, P. Franco, T. Murakami, A. Ohnishi, and H. Kurosawa, Anal. Chim. Acta, 557, 221 (2006)