Summary
The retention, enantioselectivity and enantiomeric elution order of racemic propranolol (PP) and its ester derivatives (O-acetyl,-propyl,-butyl and-valeryl PP) on an ovomucoid-bonded silica column have been investigated with respect to pH, ionic strength and organic modifier. For these cationic solutes, an increase in the organic modifier content and/or a decrease in the pH result in a decreased retention of both enantiomers. Enantioselectivity of the ester derivatives was higher than of underivated PP. The enantiomeric elution order was (S)/(R) for PP and (R)/(S) for the four ester derivatives, when ethanol or 2-propanol was used as the organic modifier. When methanol or acetonitrile was used as the organic modifier, inversion of the enantiomeric elution order was observed for O-valeryl PP with the use of methanol and for PP and O-propyl PP with acetonitrile. These results suggest that at least two chiral binding- or recognitionsites are present in a protein molecule and/or conformational changes occur in the chiral binding- or recognition-site(s) of the protein molecule bonded to a silica matrix.
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Haginaka, J., Wakai, J., Takahashi, K. et al. Chiral separation of propranolol and its ester derivatives on an ovomucoid-bonded silica: Influence of pH, ionic strength and organic modifier on retention, enantioselectivity and enantiomeric elution order. Chromatographia 29, 587–592 (1990). https://doi.org/10.1007/BF02261228
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DOI: https://doi.org/10.1007/BF02261228