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Publicly Available Published by De Gruyter January 1, 2009

Polysaccharide derivatives as useful chiral stationary phases in high-performance liquid chromatography

  • Xiaoming Chen , Chiyo Yamamoto and Yoshio Okamoto

Abstract

The chromatographic separation of enantiomers using chiral stationary phases (CSPs) has significantly advanced. The esters and carbamates of polysaccharides coated on silica gel have been extensively studied and widely used as CSPs for high-performance liquid chromatography (HPLC). In order to overcome the strict solvent limitation on these coated CSPs, the preparation of a new generation of CSPs consisting of immobilized polysaccharide derivatives has become increasingly important. The universal solvent compatibility of the new CSPs provides flexibility in both analytical and preparative chromatographies.


Conference

International Conference on Polymers and Organic Chemistry 2006 (POC'06), 12th, Okazaki, Japan, 2006-07-02–2006-07-07


References

1. doi:10.1016/S0021-9673(00)00532-X, N. M. Maier, P. Franco, W. Linder. J. Chromatogr., A 906, 3 (2001).Search in Google Scholar

2. doi:10.1016/S1359-6446(03)02904-0, H. Caner, E. Groner, L. Levy, I. Agranat. Drug Discov. Today 9, 105 (2004).Search in Google Scholar

3. A. Thayer. Chem. Eng. News 83, 49 (2005).10.1021/cen-v083n025.p049Search in Google Scholar

4. A. M. Rouhi. Chem. Eng. News 82, 47 (2004).10.1021/cen-v082n025.p047aSearch in Google Scholar

5. doi:10.1016/S0021-9673(00)00505-7, V. Schurig. J. Chromatogr., A 906, 275 (2001).Search in Google Scholar

6. V. Schurig. Trends Anal. Chem. 21, 647 (2002).10.1016/S0165-9936(02)00808-7Search in Google Scholar

7. D. W. Armstrong. LC-GC Int. 11, 22 (1998).Search in Google Scholar

8. doi:10.1055/s-1998-1675, E. Yashima, C. Yamamoto, Y. Okamoto. Synlett 344 (1998).Search in Google Scholar

9. doi:10.1002/(SICI)1521-3773(19980504)37:8<1020::AID-ANIE1020>3.0.CO;2-5, Y. Okamoto, E. Yashima. Angew. Chem., Int. Ed. 37, 1021 (1998).Search in Google Scholar

10. doi:10.1016/S0021-9673(00)00501-X, E. Yashima. J. Chromatogr., A 906, 105 (2001).Search in Google Scholar

11. K. W. Phinney. Anal. Chem. 72, 204A (2000).10.1021/ac0027542Search in Google Scholar

12. doi:10.1016/S0021-9673(00)00952-3, G. Terfloth. J. Chromatogr., A 906, 301 (2001).Search in Google Scholar

13. doi:10.1002/elps.200290015, J. Kang, D. Wistuba, V. Schurig. Electrophoresis 23, 4005 (2002).Search in Google Scholar

14. H. Y. Aboul-Enein, I. W. Wainer. The Impact of Stereochemistry on Drug Development and Use, John Wiley, New York (1997).Search in Google Scholar

15. doi:10.1016/S0021-9673(00)00951-1, E. R. Francotte. J. Chromatogr., A 906, 379 (2001).Search in Google Scholar

16. doi:10.1016/S0021-9673(00)00504-5, J. Haginaka. J. Chromatogr., A 906, 253 (2001).Search in Google Scholar

17. Z. Juvancz, J. Szejtli. Trends Anal. Chem. 21, 379 (2002).10.1016/S0165-9936(02)00506-XSearch in Google Scholar

18. doi:10.1016/S0021-9673(00)00943-2, G. Felix. J. Chromatogr., A 906, 171 (2001).Search in Google Scholar

19. doi:10.1016/S0021-9673(00)00955-9, K. Tachibana, A. Ohnishi. J. Chromatogr., A 906, 127 (2001).Search in Google Scholar

20. doi:10.1016/S0021-9673(00)00950-X, H. Y. Aboul-Enein. J. Chromatogr., A 906, 185 (2001).Search in Google Scholar

21. doi:10.1246/bcsj.77.227, C. Yamamoto, Y. Okamoto. Bull. Chem. Soc. Jpn. 77, 227 (2004).Search in Google Scholar

22. doi:10.1016/S0021-9673(00)00941-9, J. W. Timothy, B. F. Alton III. J. Chromatogr., A 906, 73 (2001).Search in Google Scholar

23. doi:10.1016/S0021-9673(00)00953-5, F. Gasparrini, D. Misiti, C. Villani. J. Chromatogr., A 906, 35 (2001).Search in Google Scholar

24. doi:10.1021/ja00330a057, Y. Okamoto, M. Kawashima, K. Hatada. J. Am. Chem. Soc. 106, 5357 (1984).Search in Google Scholar

25. doi:10.1016/S0021-9673(01)83736-5, Y. Okamoto, M. Kawashima, K. Hatada. J. Chromatogr. 363, 173 (1986).Search in Google Scholar

26. doi:10.1007/BF02282825, G. Hesse, R. Hagel. Chromatographia 6, 277 (1973).Search in Google Scholar

27. doi:10.1002/anie.198000131, G. Blaschke. Angew. Chem., Int. Ed. Engl. 19, 13 (1980).Search in Google Scholar

28. doi:10.1080/01483918608076641, G. Blaschke. J. Liq. Chromatogr. 9, 341 (1986).Search in Google Scholar

29. doi:10.1080/01483918608076640, T. Shibata, I. Okamoto, K. Ishii. J. Liq. Chromatogr. 9, 313 (1986).Search in Google Scholar

30. doi:10.1246/cl.1984.739, Y. Okamoto, M. Kawashima, K. Yamamoto, K. Hatada. Chem. Lett. 739 (1984).Search in Google Scholar

31. doi:10.1007/BF02687754, A. Ichida, T. Shibata, I. Okamoto, Y. Yuki, H. Namikoshi, Y. Toda. Chromatographia 19, 280 (1984).Search in Google Scholar

32. doi:10.1016/S0021-9673(01)94414-0, Y. Okamoto, R. Aburatani, K. Hatada. J. Chromatogr. 389, 95 (1987).Search in Google Scholar

33. doi:10.1007/BF02688543, T. Shibata, T. Sei, H. Nishimura, K. Deguchi. Chromatographia 24, 552 (1987).Search in Google Scholar

34. doi:10.1021/ja00330a057, Y. Okamoto, M. Kawashima, K. Hatada. J. Am. Chem. Soc. 106, 5357 (1984).Search in Google Scholar

35. doi:10.1016/S0021-9673(01)83736-5, Y. Okamoto, M. Kawashima, K. Hatada. J. Chromatogr. 363, 173 (1986).Search in Google Scholar

36. doi:10.1246/cl.1987.1857, Y. Okamoto, R. Aburatani, T. Fukumoto, K. Hatada. Chem. Lett. 1857 (1987).Search in Google Scholar

37. doi:10.1016/0021-9673(94)80278-5, B. Chankvetadze, E. Yashima, Y. Okamoto. J. Chromatogr., A 670, 39 (1994).Search in Google Scholar

38. doi:10.1016/0021-9673(94)00729-S, B. Chankvetadze, E. Yashima, Y. Okamoto. J. Chromatogr., A 694, 101 (1995).Search in Google Scholar

39. doi:10.1295/polymj.27.856, E. Yashima, C. Yamamoto, Y. Okamoto. Polym. J. 27, 856 (1995).Search in Google Scholar

40. doi:10.1016/S0021-9673(97)00648-1, B. Chankvetadze, L. Chankvetadze, S. Sidamonidze, E. Kasashima, E. Yashima, Y. Okamoto. J. Chromatogr., A 787, 67 (1997).Search in Google Scholar

41. doi:10.1080/01483918708066791, Y. Okamoto, R. Aburatani, S. Miura, K. Hatada. J. Liq. Chromatogr. 10, 1613 (1987).Search in Google Scholar

42. doi:10.1246/cl.2000.1176, B. Chankvetadze, C. Yamamoto, Y. Okamoto. Chem. Lett. 1176 (2000).Search in Google Scholar

43. B. Chankvetadze, C. Yamamoto, Y. Okamoto. J. Comput. Chem. High Throughput Scr. 3, 497 (2000).10.2174/1386207003331391Search in Google Scholar

44. doi:10.1016/S0021-9673(01)00958-X, B. Chankvetadze, C. Yamamoto, Y. Okamoto. J. Chromatogr., A 922, 127 (2001).Search in Google Scholar

45. doi:10.1002/marc.1983.030041202, U. Vogt, P. Zugenmaier. Makromol. Chem. Rapid Commun. 4, 759 (1983).Search in Google Scholar

46. doi:10.1021/ja992421q, T. Kubota, C. Yamamoto, Y. Okamoto. J. Am. Chem. Soc. 122, 4056 (2000).Search in Google Scholar

47. doi:10.1002/chir.10095, T. Kubota, C. Yamamoto, Y. Okamoto. Chirality 14, 372 (2002).Search in Google Scholar

48. doi:10.1246/cl.1990.909, Y. Okamoto, Y. Kaida, H. Hayashida, K. Hatada. Chem. Lett. 909 (1990).Search in Google Scholar

49. doi:10.1016/0021-9673(93)80143-V, Y. Kaida, Y. Okamoto. J. Chromatogr. 641, 267 (1993).Search in Google Scholar

50. doi:10.1246/bcsj.72.1815, C. Yamamoto, E. Yashima, Y. Okamoto. Bull. Chem. Soc. Jpn. 72, 1815 (1999).Search in Google Scholar

51. doi:10.1021/ma00149a018, D. N. Theodorou, U. W. Suter. Macromolecules 18, 1467 (1985).Search in Google Scholar

52. doi:10.1246/cl.1994.579, E. Yashima, M. Yamada, Y. Okamoto. Chem. Lett. 579 (1994).Search in Google Scholar

53. E. Yashima, M. Yamada, C. Yamamoto, M. Nakashima, Y. Okamoto. Enantiomer 2, 225 (1997).Search in Google Scholar

54. doi:10.1021/ja960050x, E. Yashima, C. Yamamoto, Y. Okamoto. J. Am. Chem. Soc. 118, 4036 (1996).Search in Google Scholar

55. doi:10.1021/ja020828g, C. Yamamoto, E. Yashima, Y. Okamoto. J. Am. Chem. Soc. 124, 12583 (2002).Search in Google Scholar

56. doi:10.1016/0008-6215(87)80122-2, H. Steinmeier, P. Zugenmaier. Carbohydr. Res. 164, 97 (1987).Search in Google Scholar

57. U. Vogt, P. Zugenmaier. Ber. Bunsen-Ges. Phys. Chem. 89, 1217 (1985).10.1002/bbpc.19850891120Search in Google Scholar

58. doi:10.1246/bcsj.63.3606, R. Aburatani, Y. Okamoto, K. Hatada. Bull. Chem. Soc. Jpn. 63, 3606 (1990).Search in Google Scholar

59. doi:10.1080/01483918708066791, Y. Okamoto, R. Aburatani, S. Miura, K. Hatada. J. Liq. Chromatogr. 10, 1613 (1987).Search in Google Scholar

60. doi:10.1016/0021-9673(94)80539-3, E. Yashima, H. Fukaya, Y. Okamoto. J. Chromatogr., A 677, 11 (1994).Search in Google Scholar

61. K. Kimata, R. Tsuboi, K. Hosoya, N. Tanaka. Anal. Meth. Instrum. 1, 23 (1993).Search in Google Scholar

62. doi:10.1016/0021-9673(95)01123-4, C. Minguillon, P. Franco, L. Oliveros, P. Lopez. J. Chromatogr., A 728, 407 (1996).Search in Google Scholar

63. doi:10.1016/S0021-9673(97)00836-4, P. Franco, C. Minguillon, L. Oliveros, P. Lopez. J. Chromatogr., A 791, 37 (1997).Search in Google Scholar

64. doi:10.1016/S0021-9673(97)01004-2, P. Franco, A. Senso, C. Minguillon, L. Oliveros. J. Chromatogr., A 796, 265 (1998).Search in Google Scholar

65. doi:10.1016/j.chroma.2004.02.007, X. Chen, F. Qin, Y. Liu, X. Huang, H. Zou. J. Chromatogr., A 1034, 109 (2004).Search in Google Scholar

66. E. Francotte. PCT WO Patent 96/27615 (1996).Search in Google Scholar

67. E. Francotte, T. Zhang. PCT WO Patent 97/044011 (1997).Search in Google Scholar

68. E. Francotte. PCT WO Patent 97/49733 (1997).Search in Google Scholar

69. doi:10.1016/S0731-7085(01)00568-4, E. Francotte, D. Huynh. J. Pharm. Biomed. Anal. 27, 421 (2002).Search in Google Scholar

70. doi:10.1021/ac960002v, N. Enomoto, S. Furukawa, Y. Ogasawara, H. Akano, Y. Kawamura, E. Yashima, Y. Okamoto. Anal. Chem. 68, 2798 (1996).Search in Google Scholar

71. doi:10.1016/S0021-9673(03)01104-X, X. Chen, Y. Liu, F. Qin, L. Kong, H. Zou. J. Chromatogr., A 1010, 185 (2003).Search in Google Scholar

72. doi:10.1016/j.chroma.2004.05.011, B. Chankvetadze, T. Ikai, C. Yamamoto, Y. Okamoto. J. Chromatogr., A 1042, 55 (2004).Search in Google Scholar

73. doi:10.1246/cl.2004.1188, T. Ikai, R. Muraki, C. Yamamoto, M. Kamigaito, Y. Okamoto. Chem. Lett. 33, 1188 (2004).Search in Google Scholar

74. doi:10.1016/S0021-9673(00)00531-8, P. Franco, A. Senso, L. Oliveros, C. Minguillon. J. Chromatogr., A 906, 155 (2001).Search in Google Scholar

75. doi:10.1295/polymj.38.91, T. Ikai, C. Yamamoto, M. Kamigaito, Y. Okamoto. Polym. J. 38, 91 (2006).Search in Google Scholar

76. doi:10.1246/cl.2001.724, T. Kubota, T. Kusano, C. Yamamoto, E. Yashima, Y. Okamoto. Chem. Lett. 724 (2001).Search in Google Scholar

77. doi:10.1002/chir.10169, T. Kubota, C. Yamamoto, Y. Okamoto. Chirality 15, 77 (2003).Search in Google Scholar

78. doi:10.1002/pola.10836, T. Kubota, C. Yamamoto, Y. Okamoto. J. Polym. Sci., Part A: Polym. Chem. 41, 3703 (2003).Search in Google Scholar

79. doi:10.1002/pola.20372, T. Kubota, C. Yamamoto, Y. Okamoto. J. Polym. Sci., Part A: Polym. Chem. 42, 4704 (2004).Search in Google Scholar

80. doi:10.1016/j.chroma.2005.11.044, X. Chen, C. Yamamoto, Y. Okamoto. J. Chromatogr., A 1104, 62 (2006).Search in Google Scholar

81. doi:10.1002/jssc.200600006, X. Chen, C. Yamamoto, Y. Okamoto. J. Sep. Sci. 29, 1432 (2006).Search in Google Scholar

82. doi:10.1021/jo051727e, T. E. Wood, A. C. Ross, N. D. Dalgleish, E. D. Power, A. Thompson, X. Chen, Y. Okamoto. J. Org. Chem. 70, 9967 (2005).Search in Google Scholar

83. doi:10.1002/anie.200602002, M. R. Kishan, A. Parham, F. Schelhase, A. Yoneva, G. Silva, X. Chen, Y. Okamoto, F. Vogtle. Angew. Chem., Int. Ed. 45, 7296 (2006).Search in Google Scholar

84. doi:10.1002/ejoc.200600437, A. Bohmer, J. Bruggemann, A. Kaufmann, A. Yoneva, S. Muller, F. W. Vergeer, L. F. Chi, L.DeCola, H. Fuchs, T. Kubota, X. Chen, Y. Okamoto, F. Vogtle. Eur. J. Org. Chem. 45 (2007).Search in Google Scholar

85. doi:10.1016/j.chroma.2005.03.116, T. Zhang, C. Kientzy, P. Franco, A. Ohnishi, Y. Kagamihara, H. Kurosawa. J. Chromatogr., A 1075, 65 (2005).Search in Google Scholar

86. doi:10.1016/j.aca.2005.10.017, T. Zhang, D. Nguyen, P. Franco, T. Murakami, A. Ohnishi, H. Kurosawa. Anal. Chim. Acta 557, 221 (2006).Search in Google Scholar

Published Online: 2009-01-01
Published in Print: 2007-01-01

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