화학공학소재연구정보센터
Macromolecular Research, Vol.15, No.2, 134-141, March, 2007
Efficient Immobilization of Polysaccharide Derivatives as Chiral Stationary Phases via Copolymerization with Vinyl Monomers
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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, play a 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.
  1. Maier NM, Franco P, Linder W, J. Chromatogr. A, 906, 3 (2001)
  2. Schurig V, J. Chromatogr. A, 906, 275 (2001)
  3. Schurig V, Trends Anal. Chem., 21, 647 (2002)
  4. Armstrong DW, LC. GC Int., 11, 22 (1998)
  5. Yashima E, Yamamoto C, Okamoto Y, Synlett, 344 (1998)
  6. Yashima E, Yamamoto C, Okamoto Y, Angew. Chem. Int. Ed., 37, 1021 (1998)
  7. Yashima E, J. Chromatogr. A, 906, 105 (2001)
  8. Phinney KW, Anal. Chem., 72, 204A (2000)
  9. Terfloth G, J. Chromatogr. A, 906, 301 (2001)
  10. Kang J, Wistuba D, Schurig V, Electroanalysis, 23, 4005 (2002)
  11. Haginaka J, J. Chromatogr. A, 906, 253 (2001)
  12. Juvancz Z, Szejtli J, Trends Anal. Chem., 21, 379 (2002)
  13. Felix G, J. Chromatogr. A, 906, 171 (2001)
  14. Tachibana K, Ohnishi A, J. Chromatogr. A, 906, 127 (2001)
  15. Aboul-Enein HY, J. Chromatogr. A, 906, 185 (2001)
  16. Yamamoto C, Okamoto Y, Bull. Chem. Soc. Jpn., 77, 227 (2004)
  17. Timothy JW, Alton BF, J. Chromatogr. A, 906, 73 (2001)
  18. Gasparrini F, Misiti D, Villani C, J. Chromatogr. A, 906, 35 (2001)
  19. Francotte E, 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. Okamoto Y, Kawashima M, Hatada K, J. Am. Chem. Soc., 106, 5357 (1984)
  21. Okamoto Y, Kawashima M, Hatada K, J. Chromatogr. A, 363, 173 (1986)
  22. Okamoto Y, Aburatani R, Miura S, Hatada K, J. Liq. Chromatogr., 10, 1613 (1987)
  23. Yashima E, Fukaya H, Okamoto Y, J. Chromatogr. A, 667, 11 (1994)
  24. Kimata K, Tsuboi R, Hosoya K, Tanaka N, Anal. Methods Instrum., 1, 23 (1993)
  25. Minguillon C, Franco P, Oliveros L, Lopez P, J. Chromatogr. A, 728, 407 (1996)
  26. Franco P, Minguillon C, Oliveros L, Lopez P, J. Chromatogr. A, 791, 37 (1997)
  27. Franco P, Senso A, Minguillon C, Oliveros L, J. Chromatogr. A, 796, 265 (1998)
  28. Chen X, Qin F, Liu Y, Huang X, Zou H, J. Chromatogr. A, 1034, 109 (2004)
  29. Francotte E, PCT WO Patent 96/27615 (1996)
  30. Francotte E, Zhang T, PCT WO Patent 97/044011 (1997)
  31. Francotte E, PCT WO Patent 97/49733 (1997)
  32. Francotte E, Huynh D, J. Pharm. Biomed. Anal., 27, 421 (2002)
  33. Enomoto N, Furukawa S, Ogasawara Y, Akano H, Kawamura Y, Yashima E, Okamoto Y, Anal. Chem., 68, 2798 (1996)
  34. Chen X, Liu Y, Qin F, Kong L, Zou H, J. Chromatogr. A, 1010, 185 (2003)
  35. Chankvetadze B, Ikai T, Yamamoto C, Okamoto Y, J. Chromatogr. A, 1042, 55 (2004)
  36. Ikai T, Muraki R, Yamamoto C, Kamigaito M, Okamoto Y, Chem. Lett., 33, 1188 (2004)
  37. Franco P, Senso A, Oliveros L, Minguillon C, J. Chromatogr. A, 906, 155 (2001)
  38. Ikai T, Yamamoto C, Kamigaito M, Okamoto Y, Polym. J., 38, 91 (2006)
  39. Kubota T, Kusano T, Yamamoto C, Yashima E, Okamoto Y, Chem. Lett., 7, 724 (2001)
  40. Kubota T, Yamamoto C, Okamoto Y, Chirality, 15, 77 (2003)
  41. Kubota T, Yamamoto C, Okamoto Y, J. Polym. Sci. A: Polym. Chem., 41(22), 3703 (2003)
  42. Kubota T, Yamamoto C, Okamoto Y, J. Polym. Sci. A: Polym. Chem., 42(18), 4704 (2004)
  43. Chen X, Yamamoto C, Okamoto Y, J. Chromatogr. A, 1104, 62 (2006)
  44. Chen X, Yamamoto C, Okamoto Y, J. Sep. Sci., 29, 1432 (2006)
  45. Wood TE, Ross AC. Dalgleish ND, Power ED, Thompson A, Chen X, Okamoto Y, J. Org. Chem., 70, 9967 (2005)
  46. Kishan MR, Parham A, Schelhase F, Yoneva A, Silva G, Chen X, Okamoto Y, Vogtle F, Angew. Chem. Int. Ed., 45, 7296 (2007)
  47. Bohmer A, Bruggemann J, Kaufmann A, Yoneva A, Muller S, Muller WM, Muller U, Vergeer FW, Chi LF, DeCola L, Fuchs H, Chen X, Kubota T, Okamoto Y, Vogtle F, Eur. J. Org. Chem., 1, 45 (2007)
  48. Zhang T, Kientzy C, Franco P, Ohnishi A, Kagamihara Y, Kurosawa H, J. Chromatogr. A, 1075, 65 (2005)
  49. Zhang T, Nguyen D, Franco P, Murakami T, Ohnishi A, Kurosawa H, Anal. Chim. Acta, 557, 221 (2006)