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2008-12-08 - Article/Dans un journal avec peer-review - Anglais - 11 page(s)

Gerbaux Pascal , De Winter Julien , Cornil David , Ravicini Katia, Pesesse Gaëlle, Cornil Jérôme , Flammang Robert, "Non Covalent Interactions between (18-Crown-6)-Tetracarboxylic Acid and Amino Acids : Electrospray Ionization Mass Spectrometry Investigation of the Chiral Recognition Processes" in Chemistry : A European Journal, 14, 35, 11039-11049

  • Edition : Wiley
  • Codes CREF : Chimie macromoléculaire (DI1315), Chimie structurale (DI1317), Sciences de la terre et du cosmos (DI1400), Chimie quantique (DI1321), Catalyses hétérogène et homogène (DI1334), Optique (DI1250), Chimie organique (DI1313)
  • Unités de recherche UMONS : Matériaux Polymères et Composites (S816), Chimie des matériaux nouveaux (S817), Chimie organique (S836)
  • Instituts UMONS : Institut de Recherche en Science et Ingénierie des Matériaux (Matériaux)
Texte intégral :

Abstract(s) :

(Anglais) Chiral recognition of enantiomers by host compounds is one of the most challenging topics in modern host-guest chemistry. Amongst the well-established methods, mass spectrometry (MS) is increasingly used nowadays, due to its low detection limit, short analysis time, and suitability for analyzing mixtures and for studying chiral effects in the gas phase. The development of electrospray-ionization (ESI) techniques provides an invaluable tool to study, in the gas phase, diastereoisomeric complex ions prepared from enantiomer ions and a chiral selector. This paper reports on an ESIMS and ESIMSMS study of the molecular mechanisms that intervene in the chiral-recognition phenomena observed between amino acids and a chiral crown ether. The modified crown ether, namely (+)-([18]crown-6)-2,3,11,12-tetracarboxylic acid, is used as the chiral selector when covalently bound on a stationary phase in liquid chromatography. This study was stimulated by the fact that, except with threonine and proline, consistent elution orders were observed, which indicates that the D enantiomers interact more strongly with the chiral selector than the L enantiomers. For proline, the lack of a primary amino group is likely to be responsible for the nonresolution of the two forms, whereas the second stereogenic center on threonine could explain the reversed elution order. In light of those observations, we performed mass spectrometry experiments to understand more deeply the enantiomeric recognition phenomena, both in solution by the enantiomer-labeled guest method and in the gas phase by gas-phase ligand-exchange ion/molecule reactions. The results have been further supported by quantum chemical calculations. One of the most interesting features of this work is the identification of a nonspecific interaction between proline and the crown ether upon ESIMS analysis.

Notes :
  • (Anglais) Publié en ligne le 27 octobre 2008
Identifiants :
  • DOI : 10.1002/chem.200801372