Skip to main content
SpringerLink
Log in

Enantiomeric Resolution of a Chiral Sulfoxide Series by LC on Synthetic Polymeric Columns with Multimodal Elution

  • Original
  • Published:
Chromatographia Aims and scope Submit manuscript

Abstract

The liquid chromatography enantiomeric separation of a series of 17 chiral sulfoxides was systematically investigated using multimodal elution with the new synthetic polymeric stationary phases P-CAP, P-CAP DP and DEAVB. The sulfoxide series was composed of aryl alkyl sulfoxides, benzoimidazole sulfoxides and the drugs modafinil, albendazole sulfoxide, omeprazole, lansoprazole, pantoprazole and rabeprazole. This work examines the effectiveness of the polymeric chiral stationary phases for the separation of chiral sulfoxides and describes the superiority of DEABV for these separations in three different elution modes. The first ever reversed phase enantiomeric separations on these columns is demonstrated.

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
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. Lin G, Li Y, Chan ASC (2001) Introduction. In: Principles and applications of asymmetric synthesis. Wiley, New York, pp 7–8

  2. Rayner DR, Gordon AJ, Mislow K (1968) J Am Chem Soc 90:4854–4860

    Article  CAS  Google Scholar 

  3. Fernandez I, Khiar N (2003) Chem Rev 103:3651–3705

    Article  CAS  Google Scholar 

  4. Harrison PWB, Kenyon J, Phillips H (1926) J Chem Soc pp 2079–2090

  5. Kuesters E, Gerber G (1997) Chromatographia 44:91–96

    Article  CAS  Google Scholar 

  6. Anderson JL, Ding J, McCulla RD, Jenks WS, Armstrong DW (2002) J Chromatogr A 946:197–208

    Article  CAS  Google Scholar 

  7. Balmer K, Persson B-A, Lagerstroem P-O (1994) J Chromatogr A 660:269–273

    Article  CAS  Google Scholar 

  8. Berthod A, Xiao TL, Liu Y, Jenks WS, Armstrong DW (2002) J Chromatogr A 955:53–69

    Article  CAS  Google Scholar 

  9. Matlin SA, Tiritan ME, Cass QB, Boyd DR (1996) Chirality 8:147–152

    Article  CAS  Google Scholar 

  10. Chankvetadze B, Yamamoto C, Okamoto Y (2001) J Chromatogr A 922:127–137

    Article  CAS  Google Scholar 

  11. Cass QB, Batigalhia F (2003) J Chromatogr A 987:445–452

    Article  CAS  Google Scholar 

  12. Belaz KRA, Coimbra M, Barreiro JC, Montanari CA, Cass QB (2008) J Pharm Biomed Anal 47:81–87

    Article  CAS  Google Scholar 

  13. Belaz KRA, Cass QB, Oliveira RV (2008) Talanta 76:146–153

    Article  CAS  Google Scholar 

  14. Cass QB, Ferreira Galatti T (2008) J Pharm Biomed Anal 46:937–944

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. Gasparrini F, Misiti D, Villani C (2003) WO 2003079002, p 25

  17. Gasparrini F, Misiti D, Villani C, Rompietti R (2003) In: Abstracts of the 15th international symposium on chirality (ISCD-15), Shizuoka, Japan, p 132

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

    Article  CAS  Google Scholar 

  19. Han X, Wang C, He L, Beesley TE, Armstrong DW (2007) Anal Bioanal Chem 387:2681–2697

    Article  CAS  Google Scholar 

  20. Montanari MLC, Cass QB, Andricopulo AD, Leitao A, Montanari CA (2005) Anal Chim Acta 545:33–45

    Article  CAS  Google Scholar 

  21. Montanari MLC, Cass QB, Leitao A, Andricopulo AD, Montanari CA (2006) J Chromatogr A 1121:64–75

    Article  CAS  Google Scholar 

  22. Batigalhia F, Zaldini-Hernandes M, Ferreira AG, Malvestiti I, Cass QB (2001) Tetrahedron 57:9669–9676

    Article  CAS  Google Scholar 

  23. Bonato PS, Paias FO (2004) J Braz Chem Soc 15:318–323

    Article  CAS  Google Scholar 

  24. Cirilli R, Ferretti R, Gallinella B, De Santis E, Zanitti L, La Torre F (2008) J Chromatogr A 1177:105–113

    Article  CAS  Google Scholar 

  25. Cass QB, Degani ALG, Cassiano NM, Pedrazolli J (2002) J Chromatogr B 766:153–160

    Article  CAS  Google Scholar 

  26. Cass QB, Lima VV, Oliveira RV, Cassiano NM, Degani ALG, Pedrazzoli J (2003) J Chromatogr B 798:275–281

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This study was supported by the Fundação de Amparo a Pesquisa do Estado de São Paulo (FAPESP). The authors also acknowledge the Conselho Nacional de Desenvolvimento Científico e Técnologico (CNPq) and the manufactures for the donations of several chiral sulfoxides. We gratefully acknowledge the support from the National Institute of Health (GM053825-11 and GM053825-12) for this work.

Author information

Authors and Affiliations

  1. Chemistry Department, Federal University of São Carlos, P.O. Box 676, São Carlos, SP, 13.565-970, Brazil

    Tiago C. Lourenço & Quezia Bezerra Cass

  2. Chemistry and Biochemistry Department, The University of Texas at Arlington, Arlington, TX, USA

    Daniel W. Armstrong

Authors
  1. Tiago C. Lourenço
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Daniel W. Armstrong
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Quezia Bezerra Cass
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Quezia Bezerra Cass.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lourenço, T.C., Armstrong, D.W. & Cass, Q.B. Enantiomeric Resolution of a Chiral Sulfoxide Series by LC on Synthetic Polymeric Columns with Multimodal Elution. Chroma 71, 361–372 (2010). https://doi.org/10.1365/s10337-009-1460-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1365/s10337-009-1460-x

Keywords

Search

Navigation