Case of enantiomer impurity identification by normal-phase chiral high- performance liquid chromatography with optical rotation and mass spectrometric detection

Journal of Chromatography A

Volumn 878, Issue 1, 2000, Pages 35-43

  Goss, Charles A ^a   Morgan, Daniel G ^a   Harbol, Kevin L ^b   Holmes, Timothy J ^a   Cook, Jeanne ^c  

^a McMahan Research Laboratories   (United States)

^b Proctor and Gamble Pharmaceuticals   (United States)

^c Novopharm USA Inc   (United States)

Author keywords

Chiral compounds; Enantiomer separation; Impurity identification; Optical rotation

Indexed keywords

ACTIVATED CARBON; ANISOLE; CYCLOHEXANONE DERIVATIVE; PALLADIUM; PHENYLPROPIONIC ACID DERIVATIVE; TOLUENE; TYROSINE METHYL ESTER;

ARTICLE; CATALYST; CHIRAL CHROMATOGRAPHY; DRUG IDENTIFICATION; DRUG IMPURITY; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; OPTICAL ROTATION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; RACEMIC MIXTURE;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MASS SPECTROMETRY; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM;

EID: 0034607560     PISSN: 00219673     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0021-9673(00)00132-1     Document Type: Article

References (50)

1. Stinson S.C. Chem. Eng. News. 70:1992;46.
2. Stinson S.C. Chem. Eng. News. 71:1993;38.
3. Stinson S.C. Chem. Eng. News. 72:1994;38.
4. Stinson S.C. Chem. Eng. News. 73:1995;44.
5. Stinson S.C. Chem. Eng. News. 75:1997;38.
6. Sheldon R.A. Chirotechnology: Industrial Synthesis of Optically Active Compounds. 1993;Marcel Dekker, New York.
7. Yeung E.S., Steenhoek L.E., Woodruff S.D., Kuo J.C. Anal. Chem. 52:1980;1399.
8. Kuo J.C., Yeung E.S. J. Chromatogr. 223:1981;321.
9. Kuo J.C., Yeung E.S. J. Chromatogr. 229:1982;293.
10. Kuo J.C., Yeung E.S. J. Chromatogr. 253:1982;199.
11. Bobbitt D.R., Yeung E.S. Anal. Chem. 56:1984;1577.
12. Bobbitt D.R., Yeung E.S. Appl. Spectrosc. 40:1986;407.
13. Reitsma B.H., Yeung E.S. Anal. Chem. 59:1987;1059.
14. Xi X., Yeung E.S. Appl. Spectrosc. 43:1989;1337.
15. Lloyd D.K., Goodall D.M., Scrivener H. Anal. Chem. 61:1989;1238.
16. Mannschreck A., Andert D., Eiglsperger E., Gmahl E., Buchner H. Chromatographia. 25:1988;182.
17. Mannschreck A., Kieβl L. Chromatographia. 28:1989;263.
18. Goss C.A., Wilson D.C., Weiser W.E. Anal. Chem. 66:1994;3093.
19. Liu G., Goodall D.M., Loran J.S. Anal. Proc. 29:1992;31.
20. Bornhop D.J., Hankins J. Anal. Chem. 68:1996;1677.
21. Mistry N., Roberts A.D., Tranter G.E., Francis P., Barylski I., Ismail I.M., Nicholson J.K., Lindon J.C. Anal. Chem. 71:1999;2838.
22. Tran C.D., Grishko V.I., Huang G. Anal. Chem. 66:1994;2630.
23. Gergely A. Tech. Instrum. Anal. Chem. 14:1994;279.
24. Rosenzweig Z., Yeung E.S. Appl. Spectrosc. 47:1993;2017.
25. Zukowski J., Tang Y., Berthod A., Armstrong D.W. Anal. Chim. Acta. 258:1992;83.
26. Bertucci C., Domenici E., Salvadori P. Chirality. 8:1990;843.
27. Xu M., Tran C.D. Anal. Chem. 62:1990;2467.
28. Meinard C., Bruneau P., Perronnet J. J. Chromatogr. 349:1985;109.
29. Brooks D.J., Perkins M.J., Smith S.L., Goodall D.M., Lloyd D.K. J. Chem. Soc. Perkin Trans. 2. 3:1992;393.
30. Boehme W., Wagner G., Oehme U., Priesnitz U. Anal. Chem. 54:1982;709.
31. Herrmann R. Dtsch. Apoth. Ztg. 122:1982;1797.
32. Rice P.D., Shao Y.Y., Erskine S.R., Teague T.G., Bobbit D.R. Talanta. 36:1989;473.
33. Mannschreck A. Chirality. 4:1992;163.
34. Däppen R., Voigt P., Maystre F., Bruno A.E. Anal. Chim. Acta. 282:1993;47.
35. De Hoffmann E., Charette J., Stroobant V. Mass Spectrometry: Principles and Applications. 1996;John Wiley & Sons, New York.
36. Busch K.L., Glish G.L., McLuckey S.A. Mass Spectrometry/Mass Spectrometry. 1988;VCH, New York.
37. Hiraoka K., Kudaka I. Rapid Commun. Mass Spectrom. 4:1990;519.
38. Gunnarsson T., Ekblad L., Karlsson A., Michelsen P., Odham G., Jergil B. Anal. Biochemistry. 254:1997;293.
39. Vanggaard J., Hansen K.T. Xenobiotica. 27:1997;901.
40. Creaser C.S., Stygall J.W., Bowen D.V., Pullen F.S. Talanta. 44:1997;1025.
41. Jandera P., Holcapek M., Theodoridis G. J. Chromatogr. A. 813:1998;299.
42. Hvattum E., Larsen Å., Uran S., Michelsen P.M., Skotland T. J. Chromatogr. B. 716:1998;47.
43. Shang D.Y., Ikonomou M.G., Macdonald R.W. J. Chromatogr. A. 849:1999;467.
44. Zavitsanos A.P., Alebic-Kolbah T. J. Chromatogr. A. 794:1998;45.
45. Alebic-Kolbah T., Zavitsanos A.P. J. Chromatogr. A. 759:1998;65.
46. Stenhoff H., Blomqvist Å., Lagerström P.-O. J. Chromatogr. B. 734:1999;191.
47. Henke B.R., Blanchard S.G., Brackeen M.F., Brown K.K., Cobb J.E., Collins J.L., W Harrington W. Jr., Hashim M.A., Hull-Ryde E.A., Kaldor I., Kliewer S.A., Lake D.H., Leesnitzer L.M., Lehmann J.M., Lenhard J.M., Orband-Miller L.A., Miller J.F., Mook R.A. Jr., Noble S.A., Oliver W. Jr., Parks D.J., Plunket K.D., Szewczyk J.R., Willson T.M. J. Med. Chem. 41:1998;5020.
48. Denny W.A., Cain B.F. J. Med. Chem. 21:1978;430.
49. K.L. Harbol, D.G. Morgan, N.P. Kitrinos, A. Rodriguez, Proceedings: 45th ASMS Conference on Mass Spectrometry and Allied Topics, Palm Springs, CA, May 1997, p. 172.
50. Wang I.H., Subramanian V., Moorman R., Burleson J., Ko J. J. Chromatogr. A. 864:1999;271.