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Screening of Pirkle-Type Chiral Stationary Phases for HPLC Enantioseparations

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Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 970))

Abstract

The majority of enantiomeric separations for purity analysis and quality control continue to be performed by normal-phase liquid chromatography and supercritical fluid chromatography. In this chapter, representative chromatographic screening procedures for the enantioseparations using Pirkle-type stationary phases are presented. As Pirkle-type phases are commonly applied to the preparative chromatographic isolation of enantiomers, volatile modifiers are used in this screen in order to be subsequently compatible with the techniques used to recover analytes from preparative scale isolations.

The Stage 1 screen presented here is used initially for screening chiral entities. The gradients use cyclohexane and ethanol both with and without chromatographic modifiers. The Stage 2 screen is used for more challenging to resolve compounds that do not exhibit resolution using the Stage 1 screening procedure.

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References

  1. Kennedy JH (1996) Comparison of chiral ­separations on polysaccharide chiral stationary phases to an improved Pirkle-type phase. J Chromatogr 725:219–224

    Article  CAS  Google Scholar 

  2. Siluveru M, Stewart JT (1996) Stereoselective determination of R(−)- and S(+)-prilocaine in human serum using a brush-type chiral stationary phase. J Pharm Biomed Anal 15:389–392

    Article  PubMed  CAS  Google Scholar 

  3. Zhang X, Ouyang J, Yang Y (2001) A simple method for chiral separation of ephedrines using (R)-1-naphthylglycine and 3,5,-dinitrobenzoic acid as stationary phase. Anal Lett 34:1851–1865

    Article  CAS  Google Scholar 

  4. Shao B-H, Xu X-Z, Wu Q-Z, Lu J-D, Fu X-Y (2005) Comparative enantioseparation of 2-arylpropionic acid esters on cellulose derivative and (S, S)-Whelk-O 1 columns. J Liq Chromatogr Rel Technol 28:63–80

    Article  CAS  Google Scholar 

  5. Shao B-H, Xu X-Z, Wu Q-Z, Lu J-D, Fu X-Y (2003) Comparison of enantioseparation and chiral recognition mechanism of racemic naproxen esters on (S,S)-Whelk-O 1 and CDMPC chiral columns. Comparison of enantioseparation and chiral recognition mechanism of racemic naproxen esters on (S,S)-Whelk-O 1 and CDMPC chiral columns. Huaxue Xuebao 61:1635–1640

    CAS  Google Scholar 

  6. Madhavan P, Rao BM, Pravin A, Kumar PR, Screenivasulu M, Chandrasekhar KB (2007) A validated chiral HPLC method for the determination of enantiomeric purity of R-β-amino-β-(4-methoxyphenyl) propionic acid. Chromatographia 65:81–84

    Article  CAS  Google Scholar 

  7. Szczerba T. (2011) Summarization of screening hits on the Whelk-O 1, RegisPack and RegisCell chiral stationary phases (CSPs). LCGC North America (Suppl):24 Feb 11, 2011

    Google Scholar 

  8. Holzheuer WB, Wong MM, Webster GK (2009) Evaluation of Pirkle-type stationary phases in chiral method development screening for compounds of pharmaceutical interest. Curr Pharm Anal 5:10–20

    Article  CAS  Google Scholar 

  9. Shibata T, Mori K, Okamoto Y (1989) Polysaccharide phases: chiral separation by LC-application to pharmaceutical compounds. In: Krstulovic AM (ed) Chiral separations by high performance liquid chromatography: applications to pharmaceutical compounds. Ellis Horwood Ltd, Chichester

    Google Scholar 

  10. Hefnawy MM, Stewart JT (1999) Resolution of nomifensine enantiomers on selected achiral and chiral stationary phases using high performance liquid chromatography. Anal Lett 32:159–171

    Article  CAS  Google Scholar 

  11. Perrin C, Vu VA, Matthijs N, Maftouh M, Massart DL, Vander Heyden Y (2002) Screening approach for chiral separation of pharmaceuticals. Part I: normal phase liquid chromatography. J Chromatogr A 947:69–83

    Article  PubMed  CAS  Google Scholar 

  12. Perrin C, Vu VA, Matthijs N, Maftouh M, Massart DL, Vander Heyden Y (2002) Screening approach for chiral separation of pharmaceuticals. Part II. Reversed-phase liquid chromatography. J Chromatogr A 966:119–134

    Article  PubMed  CAS  Google Scholar 

  13. de la Puente ML, White CT, Rivera-Sagredt A, Reilly J, Burton K, Harvey G (2003) Impact of normal-phase gradient elution in chiral chromatography: a novel, robust, efficient and rapid chiral screening procedure. J Chromatogr A 983:101–114

    Article  Google Scholar 

  14. Andersson ME, Asclan D, Clark A, Roeraade J, Hagman G (2003) Evaluation of generic chiral liquid chromatography screens for pharmaceutical analysis. J Chromatogr A 1005:83–101

    Article  PubMed  CAS  Google Scholar 

  15. Akin A, Antosz FJ, Ausec JL, Greve KF, Johnson RL, Magnusson LE, Ramstad T, Secreast SL, Seibert DS, Webster GK (2007) An orthogonal approach to chiral method development screening. Curr Pharm Anal 3:53–70

    Article  CAS  Google Scholar 

  16. Beesley TE, Lee JT (2007) Method development and optimization of enantioseparations using macrocyclic glycopeptides chiral stationary phases. In: Subramanian G (ed) Chiral separation techniques. Wiley, Weinheim

    Google Scholar 

  17. Yue H, Bu X, Young J, Raglione T (2008) Chiral method development strategies for early phase of drug development: a case study. Am Pharm Rev 11:113–118

    CAS  Google Scholar 

  18. Mangelings D, Vander Heyden Y (2008) Screening approaches for chiral separations. Adv Chromatogr 46:175–211

    Article  PubMed  CAS  Google Scholar 

  19. Ates H, Mangelings D, Vander Heyden Y (2008) Chiral separations in polar organic solvent chromatography: updating a screening strategy with new chlorine-containing polysaccharide-based selectors. J Chromatogr B 875:57–64

    Article  CAS  Google Scholar 

  20. Holzheuer WB, Wong MM, Webster GK (2009) Reverse phase chiral method development screening for compounds of pharmaceutical interest. Curr Pharm Anal 5:345–357

    Google Scholar 

  21. Webster GK, Kott L (2010) Method development for pharmaceutical chiral chromatography. In: Ahuja S, Scypinski S (eds) Handbook of modern pharmaceutical analysis, 2nd edn. Academic, New York

    Google Scholar 

  22. Younes AA, Mangelings D, Vander Heyden Y (2011) Chiral separations in normal phase liquid chromatography: enantioselectivity of recently commercialized polysaccharide-based selectors. Part I: Enantioselectivity under generic screening conditions. J Pharm Biomed Anal 55:414–423

    Article  PubMed  CAS  Google Scholar 

  23. Webster GK (2011) Comparison of chiral chromatography columns for pharmaceutical method development. In: Ahuja S (ed) Chiral separation methods for pharmaceutical and biotechnology products. Wiley Interscience, Hoboken

    Google Scholar 

  24. Regis chiral application guide. Vol 6. www.registech.com/chiral

  25. Chirex chiral HPLC separations: advanced tools and method development techniques. www.phenomenex.com

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Author information

Authors and Affiliations

  1. Abbott Laboratories, Abbott Park, IL, USA

    Gregory K. Webster

  2. Regis Technologies, Morton Grove, IL, USA

    Ted J. Szczerba

Authors
  1. Gregory K. Webster
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  2. Ted J. Szczerba
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Corresponding author

Correspondence to Gregory K. Webster .

Editor information

Editors and Affiliations

  1. , Department of Pharmaceutical Chemistry, Friedrich-Schiller-University Jena, Philosophenweg 14, Jena, 07743, Germany

    Gerhard K. E. Scriba

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Webster, G.K., Szczerba, T.J. (2013). Screening of Pirkle-Type Chiral Stationary Phases for HPLC Enantioseparations. In: Scriba, G. (eds) Chiral Separations. Methods in Molecular Biology, vol 970. Humana Press, Totowa, NJ. https://doi.org/10.1007/978-1-62703-263-6_10

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  • DOI: https://doi.org/10.1007/978-1-62703-263-6_10

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  • Publisher Name: Humana Press, Totowa, NJ

  • Print ISBN: 978-1-62703-262-9

  • Online ISBN: 978-1-62703-263-6

  • eBook Packages: Springer Protocols

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