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The Role of Temperature in Enantioseparation of Norgestrel with Native Cyclodextrins: A Combined LC and NMR Study

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Abstract

Temperature dependence (10–50 °C) of the chiral LC separation of norgestrel was studied using native CDs added to a methanol–water 1:1 eluent. α- or β-CDs gave no enantiodiscrimination, while baseline LC separation was achieved with γ-CD. 1H NMR titrations of the racemate with α-CD showed only weak complexation, while β- or γ-CDs caused enantiomeric splitting of the steroid signals. Both the chiral selectivity values and their insignificant temperature dependence measured in the γ-CD-modified LC system were successfully reproduced by NMR titrations. This agreement corroborates the intuitive view for a wider temperature range that the stability difference of the diastereomeric γ-CD/steroid complexes governs this LC enantioseparation.

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Acknowledgments

The authors are indebted to Professor Dr Csaba Szántay, Jr. for invaluable discussions and support.

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Authors and Affiliations

  1. Gedeon Richter Plc., P.O.B. 27, Budapest 10, 1475, Hungary

    Renáta Berta, Zoltán Szakács, Mónika Babják & Mária Gazdag

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  1. Renáta Berta
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  2. Zoltán Szakács
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  3. Mónika Babják
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  4. Mária Gazdag
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Correspondence to Renáta Berta.

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Berta, R., Szakács, Z., Babják, M. et al. The Role of Temperature in Enantioseparation of Norgestrel with Native Cyclodextrins: A Combined LC and NMR Study. Chroma 71 (Suppl 1), 35–42 (2010). https://doi.org/10.1365/s10337-010-1511-3

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