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

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Abstract

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.

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Acknowledgments

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

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  1. Centro de Química Medicinal da Universidade do Porto (CEQUIMED-UP), Rua de Jorge Viterbo Ferreira 228, 4050-313, Porto, Portugal

    Carla Fernandes, Maria Elizabeth Tiritan & Madalena Pinto

  2. Laboratório de Química Orgânica e Farmacêutica, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua de Jorge Viterbo Ferreira 228, 4050-313, Porto, Portugal

    Carla Fernandes, Maria Elizabeth Tiritan & Madalena Pinto

  3. Centro de Investigação em Ciências da Saúde, Instituto Superior de Ciências da Saúde-Norte-CESPU (CICS-ISCS-N-CESPU), Rua Central de Gandra 1317, 4585-116, Gandra PRD, Portugal

    Maria Elizabeth Tiritan

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  1. Carla Fernandes
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Fernandes, C., Tiritan, M.E. & Pinto, M. Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution. Chromatographia 76, 871–897 (2013). https://doi.org/10.1007/s10337-013-2469-8

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