Skip to main content
SpringerLink
Log in

Diastereomeric and enantiomeric resolution of methoxytetrahydronaphthalene derivatives, melatonin ligand receptors, by HPLC on amylose chiral stationary phases

  • Short Communications
  • Published:
Chromatographia Aims and scope Submit manuscript

Summary

Five methoxytetrahydronaphthalene derivatives, new agonist and antagonist ligands for melatonin receptors, were resolved into their diastereomers by analytical HPLC methods using derivatized amylose, chiral stationary phases. Separation was by using normal phase methodology with a mobile phase ofn-hexane-alcohol (ethanol or 2-propanol) and a silica-based amylose tris-(S)-1-phenylethylcarbamate (Chiralpak AS), or tris-3,5-dimethylphenylcarbamate (Chiralpak AD). The effects of structural variation in the solutes were noted. Baseline separation was easily obtained in many cases.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

References

  1. Fourmaintraux, E.; Depreux, D.; Lesieur, D.; Guardiola-Lemaître, B.; Bennejean, C.; Delagrange, P.; Howell, H.H.,Bioorg. Med. Chem. 1988,6, 9–13.

    Article  Google Scholar 

  2. Francotte, E.; Junker-Buchheit, A.,J. Chromatogr. 1992,576, 1–45.

    CAS  Google Scholar 

  3. Vaccher, C.; Fourmaintraux, E.; Belloli, E.; Vaccher, M.P.; Bonte, J.P.,Chromatographia 1998,48, 790–796.

    Article  CAS  Google Scholar 

  4. Shibukawa, A.; Nakagawa, T. in Chiral separations by HPLC: Krstulovic, A.M., Eds. Ellis Horwood Ltd,1989, 477.

  5. Oguni, K.; Oda, H.; Ichida, A.J. chromatogr. A. 1995,694, 91–100.

    Article  CAS  Google Scholar 

  6. Okamoto, Y.; Kaida, Y.J. Chromatogr. A 1994,666, 403–419.

    Article  CAS  Google Scholar 

  7. Liu, G.; Goodall, D.M.; Hunter, A.T.; Massey, P.R.Chirality 1994,6, 290–294.

    Article  CAS  Google Scholar 

  8. Aboul-Enein, H.Y.; Bakr, S.A.; Nicholls, P.J.J. Liq. Chromatogr. 1994,17, 1105–1110.

    CAS  Google Scholar 

  9. Instruction Manual for Chiralpak AS, Daicel Chemical Industries, Baker France.

  10. Instruction Manual for Chiralpak AD, Daicel Chemical Industries, Baker France.

  11. Kunath, A.; Theil, F.; Wagner, J.,J. Chromatogr. A 1994,684, 162–167.

    Article  CAS  Google Scholar 

  12. Okamoto, Y.; Yashima, E.Angew. Chem. Int. Ed. 1998,37, 1020–1043.

    Article  Google Scholar 

  13. Dingenen, J. inPractical Approach to Chiral Separations by Liquid Chromatography, G. Subramanian, Eds. VCH,1994, 115.

  14. Witte, D. T.; Bruggeman, F.J.; Franke, J.P.; Copinga, S.; Jansen, J.M.; De Zeeuw, R.A.Chirality 1993,5, 545–553.

    Article  CAS  Google Scholar 

  15. Jansen, J.M.; Copinga, S.; Gruppen, G.; Isakson, R.; Witte, D.T.; Grol, C.J.,Chirality 1994,6, 596–604.

    Article  CAS  Google Scholar 

  16. Caccamese, S.; Principato, G.; Viaud, M.C.; Guillaumet, G.,J. Chromatogr. A 1995,704, 83–87.

    Article  CAS  Google Scholar 

  17. Lin, S.; Engelsma, C.J. Liq. Chromatogr. and Rel. Technol. 1997,20(14), 2181–2192.

    CAS  Google Scholar 

  18. Alfredson, T.V.; Towne, R.; Elliott, M.: Griffin, B.; Abubafari, A.; Dyson, N.; Kertesz, D.J.,J. Liq. Chromatogr. and Rel. Technol 1996, 19(10), 1653–1668.

    CAS  Google Scholar 

  19. Booth, T.D.; Lough, W.J.; Saeed, M.; Noctor, T.A.G.; Wainer, I.W.,Chirality 1997,9, 173–177.

    Article  CAS  Google Scholar 

  20. Kunath, A.; Theil, F.; Jähnisch, K.J. Chromatogr. A 1996,728, 249–257.

    Article  CAS  Google Scholar 

  21. Spitzer, T.; Yashima, E.; Okamoto, Y.Chirality 1999,11, 195–200.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie Analytique, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille II-BP, rue du Pr. Laguesse, 83-3, 59006, Lille Cédex, France

    E. Belloli, C. Foulon, J. P. Bonte & C. Vaccher

  2. Institut de Chimie Pharmaceutique, Faculté des Sciences Pharmaceutiques et Biologiques, Université de Lille II-BP, rue du Pr. Laguesse, 83-3, 59006, Lille Cédex, France

    S. Yous

Authors
  1. E. Belloli
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. C. Foulon
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. Yous
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. J. P. Bonte
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. C. Vaccher
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Belloli, E., Foulon, C., Yous, S. et al. Diastereomeric and enantiomeric resolution of methoxytetrahydronaphthalene derivatives, melatonin ligand receptors, by HPLC on amylose chiral stationary phases. Chromatographia 53, 216–219 (2000). https://doi.org/10.1007/BF02491574

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02491574

Key Words

Search

Navigation