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A comprehensive chemoselective and enantioselective 2D-HPLC set-up for fast enantiomer analysis of a multicomponent mixture of derivatized amino acids

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Abstract

A feasibility study on the fast enantioselective two-dimensional HPLC separation of racemic amino acid derivatives is presented. The method involves the on-line coupling of a narrow-bore C18 RP column in the first dimension to a short enantioselective column based on nonporous 1.5 μm particles modified with quinidine carbamate as chiral selector in the second dimension. Conceptually, the system was designed to enable both time-controlled repeated transfer of fractions of the eluate and detector-controlled transfer of selected fractions from column 1 to column 2. To avoid volume overloading of the second chiral column, a narrow-bore reversed phase column was installed in the first dimension. Due to the fast (less than 1.5 minutes) enantiomer separation that occurs in the second dimension, the overall analysis time for the two-dimensional separation of a mixture of nine racemic 3,5-dinitrobenzoyl amino acids was optimized at 16 minutes.

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References

  1. Maier NM, Franco P, Lindner W (2001) J Chromatogr A 906:3–33

    Article  CAS  Google Scholar 

  2. Francotte E (2001) J Chromatogr A 906:379–397

    Article  CAS  Google Scholar 

  3. Lindner W (1996) Stereoselective synthesis. In: Helmchen G, Hoffmann RW, Mulzer J, Schaumans E (eds) Houben–Weyl (Methods of organic chemistry), vol E21. Thieme, Stuttgart, pp 193–224

  4. Ward TJ, Ill ABF (2001) J Chromatogr A 906:73–89

    Article  CAS  Google Scholar 

  5. Hermansson J, Eriksson M (1984) J Chromatogr 336:321–328

    Article  CAS  Google Scholar 

  6. Edholm LE, Lindberg C, Paulson J, Walhagen A (1988) J Chromatogr B 424:61–72

    Article  CAS  Google Scholar 

  7. Van de Merbel NC, Stenberg M, Öste R, Marko-Varga G, Gorton L, Lingeman H, Brinkman UATh (1995) Chromatographia 41:6–14

    Article  Google Scholar 

  8. Rizzi AM, Plank C (1991) J Chromatogr 557:199–213

    Article  CAS  Google Scholar 

  9. Dossena A, Galaverna G, Corradini R, Marchelli R (1993) J Chromatogr A 653:229–234

    Article  CAS  Google Scholar 

  10. Mancini F, Fiori J, Bertucci C, Cavrini V, Bragieri M, Zanotti MC, Liverani A, Borzatta V, Andrisano V (2004) J Chromatogr A 1046:67–73

    Article  CAS  Google Scholar 

  11. Chu YQ, Wainer IW (1988) Pharm Res 5:680–683

    Article  CAS  Google Scholar 

  12. Fitos I, Visy J, Simonyi M, Hermansson J (1995) J Chromatogr A 709:265–273

    Article  CAS  Google Scholar 

  13. Lämmerhofer M, Lindner W (1996) J Chromatogr A 741:33–48

    Article  Google Scholar 

  14. Lämmerhofer M, Maier NM, Lindner W (1998) Am Lab 30:71

    Google Scholar 

  15. Maier NM, Schefzick S, Lombardo GM, Feliz M, Rissanen K, Lindner W, Lipkowitz K (2002) J Am Chem Soc 124:8611–8629

    Article  CAS  Google Scholar 

  16. Piette V, Lämmerhofer M, Bischoff K, Lindner W (1997) Chirality 9:157–161

    Article  CAS  Google Scholar 

  17. Davis JM, Giddings JC (1983) Anal Chem 55:418–426

    Article  CAS  Google Scholar 

  18. Delinger SL, Davis JM (1990) Anal Chem 62:436–443

    Article  CAS  Google Scholar 

  19. Davis JM (1991) Anal Chem 63:2141–2152

    Article  CAS  Google Scholar 

  20. Schoenmakers P, Mariott P, Beens J (2003) LC-GC Europe 16:335–339

    CAS  Google Scholar 

  21. Uzunov D, Stoev G (1993) J Chromatogr A 645:233–237

    Article  CAS  Google Scholar 

  22. Bushey MM, Jorgenson JW (1990) Anal Chem 62:161–167

    Article  CAS  Google Scholar 

  23. Köhne AP, Dornberger U, Welsch T (1998) Chromatographia 48:9–16

    Article  Google Scholar 

  24. Köhne AP, Welsch T (1999) J Chromatogr A 845:463–469

    Article  Google Scholar 

  25. Hanson M, Unger KK (1996) LC-GC Int 9:650–656

    Google Scholar 

  26. Hanson M, Unger KK (1996) LC-GC Int 9:741–746

    Google Scholar 

  27. Welsch T, Mayr G, Lammers N (1997) In: Kaiser O, Kaiser RE, Gunz H, Günther W (eds) Chromatography. InCom, Düsseldorf, pp 349–358

    Google Scholar 

  28. Engelhardt H, Lamotte S, Hafner T (1997) GIT Special. GIT, Darmstadt, pp 41–44

  29. Cundy KC, Crooks PA (1983) J Chromatogr 281:17–33

    Article  CAS  Google Scholar 

  30. Gil-Av E, Schurig V (1994) J Chromatogr A 666:519–525

    Google Scholar 

  31. Diter P, Taudien S, Samuel O, Kagan HB (1994) J Org Chem 59:370–373

    Article  CAS  Google Scholar 

  32. Hamase K, Morikawa A, Ohgusu T, Lindner W, Zaitsu K (2007) J Chromatogr A 1143:105–111

    Article  CAS  Google Scholar 

Download references

Acknowledgement

Klaus Bischoff from Bischoff Chromatography (Leonberg, Germany) is gratefully acknowledged for providing the MICRA NPS 1.5-μm silica particles and for packing columns with the chemically modified chiral silica particles.

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Author notes

  1. A. Köhne

    Present address: Solvias AG, Klybeckstrasse 191, 4002, Basel, Switzerland

Authors and Affiliations

  1. Institute of Analytical and Environmental Chemistry, Ulm University, Albert-Einstein-Allee 11, 89069, Ulm, Germany

    T. Welsch, C. Schmidtkunz, B. Müller, F. Meier, M. Chlup & A. Köhne

  2. Department of Analytical Chemistry & Food Chemistry, University of Vienna, Waehringer Strasse 38, 1090, Vienna, Austria

    M. Lämmerhofer & W. Lindner

Authors
  1. T. Welsch
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  2. C. Schmidtkunz
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  3. B. Müller
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  4. F. Meier
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  5. M. Chlup
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  6. A. Köhne
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  7. M. Lämmerhofer
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  8. W. Lindner
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Corresponding authors

Correspondence to T. Welsch or W. Lindner.

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Welsch, T., Schmidtkunz, C., Müller, B. et al. A comprehensive chemoselective and enantioselective 2D-HPLC set-up for fast enantiomer analysis of a multicomponent mixture of derivatized amino acids. Anal Bioanal Chem 388, 1717–1724 (2007). https://doi.org/10.1007/s00216-007-1399-4

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  • DOI: https://doi.org/10.1007/s00216-007-1399-4

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