Skip to main content
Log in

High-performance liquid chromatographic investigation of the enantioselectivity and mechanism of chiral recognition of new cholic acid-based stationary phases

  • Originals
  • Column Liquid Chromatography
  • Published:
Chromatographia Aims and scope Submit manuscript

Summary

To elucidate the mechanism of chiral recognition of cholic acid-based stationary phases, four new cholic acid derivatives, with differently substituted carbamate or three acetoxy groups, were bonded to a hydrosilyl-modified silica gel. Their capacity to discriminate between enantiomers was evaluated in normal-phase high-performance liquid chromatography. The results were compared with those from equivalent separations on trihydroxy- and 3α-phenylcarbamate-substituted cholic acid-based bonded phases. The influence of mobile phase composition of the separation of the enantiomers of amino alcohols was shown. Different mechanisms of chiral discrimination are discussed, highlighting the influence of the nature of the carbamate on enantioselectivity.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Terabe, S.; Shibata, O.; Miyashita, Y.J. Chromatogr. 1989,480, 403–411.

    Article  CAS  Google Scholar 

  2. Gübitz, G.; Schmid, M.G.J. Chromatogr. A 1997,792, 179–225.

    Article  Google Scholar 

  3. Williams, R. W., Jr.; Fu, Z. S.; Hinze, W. L.J. Chromatogr. Sci. 1990,28, 292–302.

    CAS  Google Scholar 

  4. Hu, W.; Haraguchi, H.Bull. Chem. Soc. Jpn 1993,66, 1967–1970.

    Article  CAS  Google Scholar 

  5. Takeuchi, T.; Chu, J.; Miwa, T.Chromatographia 1998,47, 183–188.

    Article  CAS  Google Scholar 

  6. Bucaille, N.; Vaton-Chanvrier, L.; Combret, Y.; Combret, J. C.J. High Resol. Chromatogr. 1999,22, 671–678.

    Article  CAS  Google Scholar 

  7. Vaton-Chanvrier, L.; Peulon, V.; Combret, Y.; Combret, J. C.Chromatographia 1997,46, 613–622.

    Article  CAS  Google Scholar 

  8. Vaton-Chanvrier, L.; Combret, Y.; Combret, J.C.,J. Liq. Chromatogr. & Related Technol 1990,23, 2155–2167.

    Article  Google Scholar 

  9. Iuliano, A.; Salvadori, P.; Félix, G.Tetrahedron: Asymmetry 1999,10, 3353–3364.

    Article  CAS  Google Scholar 

  10. Chu, C. H.; Jonsson, E.; Auvinen, M.; Pesek, J. J.; Sandoval, J. E.Anal. Chem. 1993,65, 808–816.

    Article  CAS  Google Scholar 

  11. Berendsen, G. E.; De Galan, L.J. Liq. Chromatogr. 1978,1, 561–586.

    CAS  Google Scholar 

  12. Okamoto, Y.; Aburatani, R.; Kaida, Y.; Hatada, K.Chem. Lett. 1988, 1125–1128.

  13. Allenmark, S. G.; Andersson, S.; Möller, P.; Sanchez, D.Chirality 1995,7, 248–256.

    Article  CAS  Google Scholar 

  14. Tang, Y.Chirality 1996,8, 136–142.

    Article  CAS  Google Scholar 

  15. Sudo, Y.; Yamaguchi, T.; Shinbo, T.J. Chromatogr. A 1996,736, 39–49.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vaton-Chanvrier, L., Combret, Y. & Combret, J.C. High-performance liquid chromatographic investigation of the enantioselectivity and mechanism of chiral recognition of new cholic acid-based stationary phases. Chromatographia 54, 31–37 (2001). https://doi.org/10.1007/BF02491829

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02491829

Key Words

Navigation