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Enantioseparations by High-Performance Liquid Chromatography Based on Chiral Ligand Exchange

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Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 1985))

Abstract

Although the first application of chiral ligand-exchange chromatography (CLEC) in HPLC dates back to late 1960s, this enantioselective strategy still represents the elective choice for the direct analysis of compounds endowed with chelating moieties. As a specific feature of the CLEC mechanism, the interaction between the chiral selector and the enantiomer does not take place in direct contact. Indeed, it is mediated by a central metal ion that, acting as a Lewis acid, simultaneously coordinates the two species, selector and analyte, through the activation of dative bonds. As a consequence, two diastereomeric mixed ternary complexes are generated in the column, ultimately leading to the stereoisomeric discrimination. CLEC applications can be carried out both with the chiral selector included in the mobile phase (chiral mobile phase, CMP), or as a part of the stationary phase. In the latter case, the chiral selector can be either covalently immobilized onto a solid support (bonded CSP, B-CSP) or physically adsorbed onto a conventional packing material, coated chiral stationary phase (C-CSP).

In this chapter, a selection of CLEC applications with CMP- and C-CSP-based chiral systems is presented.

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, University of Perugia, Perugia, Italy

    Federica Ianni, Lucia Pucciarini, Andrea Carotti, Roccaldo Sardella & Benedetto Natalini

Authors
  1. Federica Ianni
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  2. Lucia Pucciarini
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  3. Andrea Carotti
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  4. Roccaldo Sardella
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  5. Benedetto Natalini
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Corresponding author

Correspondence to Roccaldo Sardella .

Editor information

Editors and Affiliations

  1. Department of Pharmaceutical Chemistry, University of Jena, Jena, Germany

    Gerhard K. E. Scriba

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Ianni, F., Pucciarini, L., Carotti, A., Sardella, R., Natalini, B. (2019). Enantioseparations by High-Performance Liquid Chromatography Based on Chiral Ligand Exchange. In: Scriba, G.K.E. (eds) Chiral Separations. Methods in Molecular Biology, vol 1985. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9438-0_15

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  • DOI: https://doi.org/10.1007/978-1-4939-9438-0_15

  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-4939-9437-3

  • Online ISBN: 978-1-4939-9438-0

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