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Enantiomeric Resolution of Benzoxazolinonic Aminoalcohols, Potential Adrenergic Ligands, by LC and CE

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Abstract

Benzoxazolinone amino alcohols are chiral derivatives that carry one asymmetric center. Both capillary electrophoresis and high-performance liquid chromatography (LC) techniques were used to separate enantiomers with high resolution and thus permitted the determination of enantiomeric excess. Highly sulfated and anionic cyclodextrins were used as chiral selectors under CE conditions. Amylose and cellulose chiral stationary phases were used for LC for the enantioseparation of five racemic compounds. Separations were carried out on a Chiralpak AS column with various polar organic modifiers. The HPLC method appeared more to be more sensitive and was subsequently validated in terms of limits of detection and quantification. LC detection was based on UV and evaporating light scattering.

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References

  1. Vaccher MP, Lesieur D, Lespagnol C, Bonte JP, Lamar JC, Beaughard M, Dureng G (1986) Farmaco 41:257–269

    CAS  Google Scholar 

  2. Lamar JC, Beaughard M, Dureng G, Baissat J, Michelin MT, Piris P (1982) J Pharmacol 13:152–157

    Google Scholar 

  3. Bonte JP, Piancastelli MC, Lesieur I, Lamar JC, Beaughard M, Dureng G (1990) Eur J Med Chem 25:361–368. doi:10.1016/0223-5234(90)90120-R

    Article  CAS  Google Scholar 

  4. Patentansprüche WO/2007/104772 A1 Neue enantiomerenreine β-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel

  5. Dylag T, Zygmunt M, Maciag D, Handzlik J, Bednarski M, Filipek B, Kiec-Kononowicz K (2004) Eur J Med Chem 39:1013–1027. doi:10.1016/j.ejmech.2004.05.008

    Google Scholar 

  6. Vespalec R, Bocek P (1999) Electrophoresis 20:2579–2591. doi:10.1002/(SICI)1522-2683(19990901)20:13<2579::AID-ELPS2579>3.0.CO;2-R

    Article  CAS  Google Scholar 

  7. Chankvetadze B, Blaschke G (2001) J Chromatogr A 906:309–363. doi:10.1016/S0021-9673(00)01124-9

    Article  CAS  Google Scholar 

  8. Gübitz G, Schmid MG (2000) Electrophoresis 2:4112–4135. doi:10.1002/1522-2683(200012)21:18<4112::AID-ELPS4112>3.0.CO;2-T

    Article  Google Scholar 

  9. Chankvetadze B (1997) Capillary electrophoresis in chiral analysis. Wiley, Chichester

    Google Scholar 

  10. Fanali S (1997) J Chromatogr A 792:227–264. doi:10.1016/S0021-9673(97)00809-1

    Article  CAS  Google Scholar 

  11. Goel TV, Nikelly JG, Simpson RC, Matuszewski BK (2004) J Chromatogr A 1027:213–221. doi:10.1016/j.chroma.2003.08.082

    Article  CAS  Google Scholar 

  12. Avula B, Upparapalli SK, Khan IA (2005) Chromatographia 62:151–157. doi:10.1365/s10337-005-0598-4

    Article  CAS  Google Scholar 

  13. Guohua D, Qin L, Jianwei X, Liuhong Y, Bohua Z, Keliang L (2005) Chromatographia 61:527–531. doi:10.1365/s10337-005-0540-9

    Article  Google Scholar 

  14. Le Potier I, Tamisier-Karolak SL, Morin P, Megel F, Taverna M (1998) J Chromatogr A 829:341–349. doi:10.1016/S0021-9673(98)00793-6

    Article  Google Scholar 

  15. Chen Z, Yu Y, Li L (2005) J Sep Sci 28:193–196. doi:10.1002/jssc.200401804

    Article  CAS  Google Scholar 

  16. Chankvetadze B, Burjanadze N, Blaschke G (2002) J Pharm Biomed Anal 27:153–159. doi:10.1016/S0731-7085(01)00552-0

    Article  CAS  Google Scholar 

  17. Chilmonczyk Z, Ksycinska H, Lisowaka-Kuźmicz M, Jończyk A, Mazgajska M, Jarończyk M, Strzelczyk A, Aboul-Enein HY (2005) Anal Chim Acta 536:7–13. doi:10.1016/j.aca.2004.12.032

    Article  CAS  Google Scholar 

  18. Chilmonczyk Z, Ksycinska H, Mazgajska M, Cybulski J, Kaliszan R (1997) J Chromatogr A 788:81–85. doi:10.1016/S0021-9673(97)00714-0

    Article  Google Scholar 

  19. Bielejewska A, Duszczyk K, Kulig K, Malawska B, Miškiewicz M, Leš A, Žukowski J (2007) J Chromatogr A 1173:52–57. doi:10.1016/j.chroma.2007.09.070

    Article  CAS  Google Scholar 

  20. Chankvetadze B, Endresz G, Blaschke G (1994) Electrophoresis 15:804–807. doi:10.1002/elps.11501501113

    Article  CAS  Google Scholar 

  21. Lin C, Deng Y Jr, Liao W, Sun S, Lin W, Chen C (2004) J Chromatogr A 1051:283–290

    CAS  Google Scholar 

  22. Chen FT, Shen G, Evangelista R (2001) J Chromatogr A 924:523–532. doi:10.1016/S0021-9673(01)00757-9

    Article  CAS  Google Scholar 

  23. Wren SAC, Rowe RC (1992) J Chromatogr 603:235–241. doi:10.1016/0021-9673(92)85366-2

    Article  CAS  Google Scholar 

  24. Wren SAC, Rowe RC (1993) J Chromatogr 635:113–118. doi:10.1016/0021-9673(93)83120-H

    Article  CAS  Google Scholar 

  25. Palmarsdottir S, Edholm LE (1994) J Chromatogr 666:337–350. doi:10.1016/0021-9673(94)80394-3

    Article  CAS  Google Scholar 

  26. Yang WC, Yu AM, Yu XD, Chen HY (2001) Electrophoresis 22:2025–2031. doi:10.1002/1522-2683(200106)22:10<2025::AID-ELPS2025>3.0.CO;2-M

    Article  CAS  Google Scholar 

  27. Dan N, Ganesan R, Flood KG, Tsai D, Reif VD (2000) J Chromatogr A 891:115–127. doi:10.1016/S0021-9673(00)00621-X

    Article  CAS  Google Scholar 

  28. Stalcup AM, Gahm KH (1996) Anal Chem 68:1360–1368. doi:10.1021/ac950764a

    Article  CAS  Google Scholar 

  29. De Boer T, De Zeeuw RA, De Jong GJ, Ensing K (2000) Electrophoresis 21:3220–3229. doi:10.1002/1522-2683(20000901)21:15<3220::AID-ELPS3220>3.0.CO;2-X

    Article  Google Scholar 

  30. Altria KD (1996) Capillary electrophoresis guidebook: principles, instrumentation, and applications, vol 52. Humana Press, Hertfordshire, UK, pp 49–60

    Google Scholar 

  31. Chilmonczyk Z, Ksycinska H, Mazgajska M, Aboul-Enein HY (1999) Chirality 11:790–794. doi:10.1002/(SICI)1520-636X(1999)11:10<790::AID-CHIR9>3.0.CO;2-1

    Article  CAS  Google Scholar 

  32. Alfredson TV, Towne R, Elliott M, Griffin B, Abubakari A, Dyson N, Kertesz DJ (1996) J Liq Chromatogr 19:1653–1668. doi:10.1080/10826079608005499

    Article  CAS  Google Scholar 

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Correspondence to Claude Vaccher.

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Lipka, E., Vaccher, C. & Bonte, JP. Enantiomeric Resolution of Benzoxazolinonic Aminoalcohols, Potential Adrenergic Ligands, by LC and CE. Chroma 69, 465–472 (2009). https://doi.org/10.1365/s10337-008-0940-8

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