Investigation of the enantioselective separations of α-alkylarylcarboxylic acids on an amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase using quantitative structure-enantioselective retention relationships identification of a conformationally driven chiral recognition mechanism

Journal of Chromatography A

Volumn 737, Issue 2, 1996, Pages 157-169

  Booth, Tristan D ^a   Wainer, Irving W ^b,c  

^a MCGILL UNIVERSITY   (Canada)

^b MCGILL UNIVERSITY   (Canada)

^c MONTREAL GENERAL HOSPITAL   (Canada)

Author keywords

Amylose tris(3,5 dimethylphenylcarbamate); Benoxaprofen; Chiral stationary phases; Enantiomer separation; Enantioselectivity; LC; Molecular modelling; Quantitative structure retention relationships

Indexed keywords

BENOXAPROFEN; CARBOXYLIC ACID DERIVATIVE; KETOPROFEN; PHENYLACETIC ACID; SUPROFEN;

ARTICLE; CHIRALITY; COMPUTER SIMULATION; DRUG PURIFICATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; TECHNIQUE;

EID: 0029895659     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/0021-9673(96)00011-8     Document Type: Article

References (48)

1. B. Koppenhoefer, A. Nothdurft, J. Pierrot-Sanders, P. Piras, C. Popescu, C. Roussel, M. Stiebler and U. Trettin, Chirality, 5 (1993) 213-219.
2. Chiral Technologies, Application Guide for Chiral Column Selection, 2nd ed.
3. I.W. Wainer, A Practical Guide to the Selection and Use of HPLC Chiral Stationary Phases, J.T. Baker, Phillipsburg, NJ, 1988.
4. A. Berthod, S.C. Chang and D.W. Armstrong, Anal. Chem., 64 (1992) 395-404.
5. U. Norrinder and J. Hermansson, Chirality, 3 (1991) 422-426.
6. K.B. Lipkowitz, J. Chromatogr. A, 694 (1995) 15-37.
7. R. Kaliszan, Quantitative Structure-Retention Relationships, Wiley, New York, 1987.
8. R. Kaliszan, J. Chromatogr. A, 656 (1993) 417-435.
9. R. Kaliszan, T.A.G. Noctor and I.W. Wainer, Chromatographia, 33 (1992) 546-550.
10. R. Kaliszan, A. Kaliszan, T.A.G. Noctor, W.P. Purcell and I.W. Wainer, J. Chromatogr., 609 (1992) 69-81.
11. R. Kaliszan, T.A.G. Noctor and I.W. Wainer, Mol. Pharmacol., 42 (1992) 512-517.
12. R.M. Wolf, E. Francotte and D. Lohman, J. Chem. Soc., Perkin Trans. II, (1988) 893-901.
13. B.C. Cupid, J.K. Nicholson, P. Davis, R.J. Ruane, I.D. Wilson, R.C. Glen, V.S. Rose, C.R. Beddell and J.C. Lindon, Chromatographia, 37 (1993) 241-248.
14. K. Azzaoui and L. Morin-Allory, Chromatographia, 40 (1995) 690-696.
15. T.D. Booth, H. Fieger, B. Knoche and I.W. Wainer, Proceedings of the 4th International Symposium on Chiral Discrimination, Montreal, 1993, Abstract No. 218, p. 109.
16. E. Francotte and R.M. Wolf, Chirality, 2 (1990) 16-31.
17. E. Francotte and D. Lohmann, Helv. Chim. Acta, 70 (1987) 1569-1582.
18. E. Francotte and R.M. Wolf, Chirality, 3 (1991) 43-55.
19. E. Francotte, R.M. Wolf and D. Lohman, J. Chromatogr., 347 (1985) 25-37.
20. C. Roussel and C. Popescu, Chirality, 6 (1994) 251-260.
21. R. Isaksson, H. Wennerstrom and O. Wennerstrom, Tetrahedron, 44 (1988) 1697-1701.
22. I.W. Wainer and M.C. Alembik, J. Chromatogr., 358 (1986) 85-93.
23. I.W. Wainer and R.M. Stiffin, J. Chromatogr., 411 (1987) 139-151.
24. E. Yashima, M. Yamada, Y. Kaida and Y. Okamoto, J. Chromatogr. A, 694 (1995) 347-354.
25. E. Yashima, M. Yamada and Y. Okamoto, Chem. Lett., (1994) 579-582.
26. Y. Okamoto, R. Aburatini, Y. Kadia and K. Hatada, Chem. Lett., (1988) 1125-1128.
27. Y. Okamoto, R. Aburatini, Y. Kadia and K. Hatada, N. Inotsume and M. Nakano, Chirality, 1 (1989) 239-242.
28. J.P. McCarthy, J. Chromatogr. A, 685 (1994) 349-355.
29. A. Kunath, F. Theil and J. Wagner, J. Chromatogr. A, 684 (1994) 162-167.
30. E. Yashima, H. Fukaga and Y. Okamoto, J. Chromatogr. A, 677 (1994) 11-19.
31. Y. Okamoto, Y. Kadia, R. Aburatini and K. Hatada, in S. Ahuja (Editor), Chiral Separations by Liquid Chromatography (ACS Symposium Series, No. 471), American Chemical Society, Washington, DC, 1991, Ch. 5, p. 101.
32. K. Oguni, H. Oda and A. Ichida, J. Chromatogr. A, 694 (1995) 91-100.
33. Y. Okamoto and Y. Kaida, J. Chromatogr. A, 666 (1994) 403-419.
34. S.A. Matlin, M.E. Tiritan, A.J. Crawford, Q.B. Cass and D.R. Boyd, Chirality, 6 (1992) 389-394.
35. S. Abu-Lafi, M. Sterin, S. Levin and R. Mechoulam, J. Chromatogr. A, 664 (1994) 159-167.
36. S. Levin, M. Sterin and S. Abu-Lafi, Chirality, 7 (1995) 140-146.
37. H.W. William, Chirality, 6 (1994) 216-219.
38. I.W. Wainer and M.C. Alembik, J. Chromatogr., 367 (1986) 59-68.
39. U. Vogt and P. Zugenmaier, Ber. Bunsenges. Phys. Chem., 89 (1986) 983.
40. U. Vogt and P. Zugenmaier, presented at the European Science Foundation Workshop on Scientific Interaction in Polysaccharide Systems, Uppsala, 1983.
41. S.G. Allenmark, Chromatographic Enantioseparation, Methods and Application, Ellis Horwood, Chichester, 1988.
42. L.R. Hanton, C.A. Hunter and D.H. Purvis, J. Chem. Soc. Chem. Commun., (1992) 1134-1136.
43. W. Melander, D.E. Campbell and C. Horváth, J. Chromatogr., 158 (1978) 215-225.
44. K.B. Sentell and A.N. Henderson, Anal. Chim. Acta, 246 (1991) 139-149.
45. W.H. Pirkle and D.W. House, J. Org. Chem., 44 (1979) 1957-1960.
46. W.H. Pirkle and M.H. Hyun, J. Chromatogr., 328 (1985) 1-9.
47. E. Yashima, M. Yamada and Y. Okamoto, Chem. Lett., (1994) 579-582.
48. Y. Okamoto, personal communication.