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Chiral Recognition with Macrocyclic Glycopeptides: Mechanisms and Applications

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Chiral Recognition in Separation Methods

Abstract

The macrocyclic glycopeptide chiral selectors are natural molecules produced by bacterial fermentation. Purified and bonded to silica particles, they make very useful chiral stationary phases (CSP) with a broad spectrum of applicability in enantiomeric separation. The macrocyclic glycopeptide CSPs are multimodal, the same column being able to work in normal phase mode with apolar mobile phase, in reversed-phase mode, or in polar ionic mode with 100% alcoholic mobile phase of adjusted pH. The role of the carbohydrate units is described as well as the critical charge–charge docking interaction responsible for the amino acid enantiomer recognition. The complimentary phenomenon is also exposed.

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Authors and Affiliations

  1. Laboratoire des Sciences Analytiques, Université de Lyon, CNRS UMR 5180, Bat. CPE, 69622, Villeurbanne, France

    Alain Berthod

  2. Department of Chemistry, University of Texas-Arlington, 700 Planetarium Place, Arlington, TX, 76019-0065, USA

    Hai Xiao Qiu & Daniel W. Armstrong

  3. Chemistry Department, BioChemMack S&T, Lomonosov State University, b1/11 Leninskie Gory, Moscow, 119992, Russia

    Sergey M. Staroverov & Mikhail A. Kuznestov

Authors
  1. Alain Berthod
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  2. Hai Xiao Qiu
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  3. Sergey M. Staroverov
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  4. Mikhail A. Kuznestov
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  5. Daniel W. Armstrong
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Correspondence to Alain Berthod .

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Editors and Affiliations

  1. , CNRS UMR 5180, University of Lyon, Villeurbanne Cédex, 69622, France

    Alain Berthod

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Berthod, A., Qiu, H.X., Staroverov, S.M., Kuznestov, M.A., Armstrong, D.W. (2010). Chiral Recognition with Macrocyclic Glycopeptides: Mechanisms and Applications. In: Berthod, A. (eds) Chiral Recognition in Separation Methods. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-12445-7_7

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