Skip to main content

Advertisement

SpringerLink
Log in

Preparation and evaluation of a new synthetic polymeric chiral stationary phase for HPLC based on the trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide monomer

  • Original Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

A new synthetic polymeric chiral stationary phase for liquid chromatography was prepared via free-radical-initiated polymerization of trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide. The new polymeric chiral stationary phase (CSP) showed enantioselectivity for many chiral compounds in multiple mobile phases. High stability and sample capacities were observed on this polymeric chiral stationary phase. Mobile phase components and additives affected chiral separation greatly. This new synthetic chiral stationary phase is complementary to two other related commercially available CSPs: the P-CAP and P-CAP-DP columns. Interactions between the chiral stationary phase and analytes that lead to retention and chiral recognition include hydrogen bonding, dipolar, and π–π interactions. Repulsive (steric) interactions also contribute to chiral recognition.

LC chromatograms showing the analytical (blue) and preparative (red) separations of N-(3,5-dinitrobenzoylleucine) enantiomers on a new synthetic polymeric chiral stationary phase

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Armstrong DW (1997) LC-GC 59:S20–S28

    Google Scholar 

  2. Armstrong DW, Zhang B (2001) Anal Chem 73:557A–561A

    CAS  Google Scholar 

  3. Gasparrini F, Misiti D, Villani C (2001) J Chromatogr A 906:35–50

    Article  CAS  Google Scholar 

  4. Yamamoto C, Okamoto Y (2004) Bull Chem Soc Jpn 77:227–257

    Article  CAS  Google Scholar 

  5. Okamoto Y, Yashima E (1998) Angew Chem Int Ed 37:1020–1043

    Article  Google Scholar 

  6. Gasparrini F, Misiti D, Villani C (2003) WO Patent 2003079002

  7. Gasparrini F, Misiti D, Rompietti R, Villani C (2005) J Chromatogr A 1064:25–38

    Article  CAS  Google Scholar 

  8. Zhong Q, Han X, He L, Beesley TE, Trahanovsky WS, Armstrong DW (2005) J Chromatogr A 1066:55–70

    Article  CAS  Google Scholar 

  9. Han X, He L, Zhong Q, Beesley TE, Armstrong DW (2006) Chromatographia 63:13–23

    Article  CAS  Google Scholar 

  10. Blaschke G, Donow F (1975) Chem Ber 108:1188–1197

    Article  CAS  Google Scholar 

  11. Blaschke G, Donow F (1975) Chem Ber 108:2792–2798

    Article  CAS  Google Scholar 

  12. Blaschke G (1980) Angew Chem Int Ed 19:13–24

    Article  Google Scholar 

  13. Okamoto Y, Honda S, Okamoto I, Yuki H, Murata S, Noyori R, Tanaka H (1981) J Am Chem Soc 103:6971–6973

    Article  CAS  Google Scholar 

  14. Okamoto Y, Yashima E, Hatada K, Mislow K (1984) J Org Chem 49:557–558

    Article  CAS  Google Scholar 

  15. Okamoto Y, Mohri H, Hatada K (1989) Polym J 21:439–445

    Article  CAS  Google Scholar 

  16. Allenmark SG, Andersson S, Möller P, Sanchez D (1995) Chirality 7:248–256

    Article  CAS  Google Scholar 

  17. Thunberg L, Allenmark S, Friberg A, Ek F, Frejd T (2004) Chirality 16:614–624

    Article  CAS  Google Scholar 

  18. Thunberg L, Allenmark S (2004) J Chromatogr A 1026:65–76

    Article  CAS  Google Scholar 

  19. Blaschke G, Bröker W, Fraenkel W (1980) Angew Chem Int Ed 25:830–831

    Google Scholar 

  20. Saotome Y, Miyazawa T, Endo T (1989) Chromatographia 28:505–508

    Article  CAS  Google Scholar 

  21. Arlt D, Bömer B, Grosser R, Lang W (1991) Angew Chem Int Ed 30:1662–1664

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the support of this work by the National Institutes of Health, NIH RO1 GM53825-11.

Author information

Authors and Affiliations

  1. Chemistry & Biochemistry Department, The University of Texas at Arlington, Arlington, TX, 76019, USA

    Xinxin Han, Chunlei Wang & Daniel W. Armstrong

  2. Advanced Separation Technologies Inc., 37 Leslie Court, P.O. Box 297, Whippany, NJ, 07981, USA

    Lingfeng He & Thomas E. Beesley

Authors
  1. Xinxin Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Chunlei Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Lingfeng He
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Thomas E. Beesley
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Daniel W. Armstrong
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Daniel W. Armstrong.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Han, X., Wang, C., He, L. et al. Preparation and evaluation of a new synthetic polymeric chiral stationary phase for HPLC based on the trans-9,10-dihydro-9,10-ethanoanthracene-(11S,12S)-11,12-dicarboxylic acid bis-4-vinylphenylamide monomer. Anal Bioanal Chem 387, 2681–2697 (2007). https://doi.org/10.1007/s00216-007-1154-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-007-1154-x

Keywords

Search

Navigation