Molecular recognition of the hplc whelk-o1 selector towards the conformational enantiomers of nevirapine and oxcarbazepine

Roberta Franzini, Marco Pierini, Andrea Mazzanti, Antonia Iazzetti, Alessia Ciogli, Claudio Villani

Risultato della ricerca: Contributo in rivistaArticolo in rivista


The presence of stereogenic elements is a common feature in pharmaceutical compounds, and affording optically pure stereoisomers is a frequent issue in drug design. In this context, the study of the chiral molecular recognition mechanism fundamentally supports the understanding and opti-mization of chromatographic separations with chiral stationary phases. We investigated, with molecular docking, the interactions between the chiral HPLC selector Whelk-O1 and the stereoisomers of two bioactive compounds, the antiviral Nevirapine and the anticonvulsant Oxcarbazepine, both char-acterized by two stereolabile conformational enantiomers. The presence of fast-exchange enantiomers and the rate of the interconversion process were studied using low temperature enantioselective HPLC and VT-NMR with Whelk-O1 applied as chiral solvating agent. The values of the energetic barriers of interconversion indicate, for the single enantiomers of both compounds, half-lives suffi-ciently long enough to allow their separation only at critically sub-ambient temperatures. The chiral selector Whelk-O1 performed as a strongly selective discriminating agent both when applied as a chiral stationary phase (CSP) in HPLC and as CSA in NMR spectroscopy.
Lingua originaleEnglish
pagine (da-a)1-14
Numero di pagine14
RivistaInternational Journal of Molecular Sciences
Stato di pubblicazionePubblicato - 2021


  • Chiral molecular recognition
  • Chirality
  • Conformational chirality
  • Dynamic chromatography
  • Enantioselective HPLC
  • Molecular docking
  • Stereodynamics
  • Tricyclic drugs
  • VT-NMR


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