, Volume 76, Issue 15–16, pp 871–897 | Cite as

Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution

  • Carla Fernandes
  • Maria Elizabeth Tiritan
  • Madalena PintoEmail author


This review focuses on the evolution of Pirkle-type chiral stationary phases (CSPs), based on chiral recognition mechanism of small molecules and applications directly related with Medicinal Chemistry. Therefore, the strategies to plan these chiral selectors for enantioseparation of diverse therapeutic classes of chiral drugs and the understanding of the recognition mechanism are emphasized. The planning of Pirkle and co-workers to design different classes of CSPs was initially based on NMR studies, following the principle of reciprocity together with chromatographic results and studies of chiral recognition phenomena. All those features are described and critically discussed in this review. Finally, based on general principles established by Pirkle’s work it can be inferred that diverse chiral small molecules can be successfully used as chromatographic tools for enantiomeric resolution. In this context, several research groups were inspired on Pirkle’s design to develop new CSPs. Xanthone derivatives bonded to chiral groups were also exploited as selectors for CSPs and are briefly reported.


HPLC Chiral stationary phase Chirality Chiral recognition Enantioresolution Xanthone derivatives 



FCT—Fundação para a Ciência e a Tecnologia under the project CEQUIMED-PEst-OE/SAU/UI4040/2011.


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Copyright information

© Springer-Verlag Berlin Heidelberg 2013

Authors and Affiliations

  • Carla Fernandes
    • 1
    • 2
  • Maria Elizabeth Tiritan
    • 1
    • 2
    • 3
  • Madalena Pinto
    • 1
    • 2
    Email author
  1. 1.Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP)PortoPortugal
  2. 2.Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de FarmáciaUniversidade do PortoPortoPortugal
  3. 3.Centro de Investigação em Ciências da Saúde, Instituto Superior de Ciências da Saúde-Norte-CESPU (CICS-ISCS-N-CESPU)Gandra PRDPortugal

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