Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive
Abstract
A simple and rapid TLC method using beta-cyclodextrin as a chiral mobile phase additive (CMPA) was developed for direct separation of S-clopidogrel and its impurity R-clopidogrel. The influence of different factors (stationary phases, organic modifiers, chiral selectors and their concentrations in the mobile phase, and optimal saturation time of the chamber) on enantioseparation was studied. The best resolution of clopidogrel enantiomers was achieved on Polygram (R) cel 300 Ac-10% plates using isopropanol-0.5 mM beta-cyclodextrin (6: 4, v/v) as mobile phase in TLC chamber previously equilibrated with the mobile phase for 20 min. The spots were detected under UV light and using iodine vapours. The method enables rapid separation of clopidogrel enantiomers and can be successfully used in control of stereoselective synthesis of clopidogrel and in control of its purity. Finally, the molecular modelling of the inclusion complexes between the analytes and alpha-, beta-, and gamma-cyclodextri...n was performed to investigate the mechanism of the enantiorecognition.
Keywords:
clopidogrel / enantioseparation / chiral impurity / TLC / beta-cyclodextrinSource:
Acta Chromatographica, 2011, 23, 2, 235-245Publisher:
- Akademiai Kiado Rt, Budapest
Funding / projects:
DOI: 10.1556/AChrom.23.2011.2.4
ISSN: 1233-2356
WoS: 000291343100004
Scopus: 2-s2.0-79958847889
Collections
Institution/Community
PharmacyTY - JOUR AU - Antić, Dušan AU - Filipić, Slavica AU - Ivković, Branka AU - Nikolić, Katarina AU - Agbaba, Danica PY - 2011 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1564 AB - A simple and rapid TLC method using beta-cyclodextrin as a chiral mobile phase additive (CMPA) was developed for direct separation of S-clopidogrel and its impurity R-clopidogrel. The influence of different factors (stationary phases, organic modifiers, chiral selectors and their concentrations in the mobile phase, and optimal saturation time of the chamber) on enantioseparation was studied. The best resolution of clopidogrel enantiomers was achieved on Polygram (R) cel 300 Ac-10% plates using isopropanol-0.5 mM beta-cyclodextrin (6: 4, v/v) as mobile phase in TLC chamber previously equilibrated with the mobile phase for 20 min. The spots were detected under UV light and using iodine vapours. The method enables rapid separation of clopidogrel enantiomers and can be successfully used in control of stereoselective synthesis of clopidogrel and in control of its purity. Finally, the molecular modelling of the inclusion complexes between the analytes and alpha-, beta-, and gamma-cyclodextrin was performed to investigate the mechanism of the enantiorecognition. PB - Akademiai Kiado Rt, Budapest T2 - Acta Chromatographica T1 - Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive VL - 23 IS - 2 SP - 235 EP - 245 DO - 10.1556/AChrom.23.2011.2.4 ER -
@article{ author = "Antić, Dušan and Filipić, Slavica and Ivković, Branka and Nikolić, Katarina and Agbaba, Danica", year = "2011", abstract = "A simple and rapid TLC method using beta-cyclodextrin as a chiral mobile phase additive (CMPA) was developed for direct separation of S-clopidogrel and its impurity R-clopidogrel. The influence of different factors (stationary phases, organic modifiers, chiral selectors and their concentrations in the mobile phase, and optimal saturation time of the chamber) on enantioseparation was studied. The best resolution of clopidogrel enantiomers was achieved on Polygram (R) cel 300 Ac-10% plates using isopropanol-0.5 mM beta-cyclodextrin (6: 4, v/v) as mobile phase in TLC chamber previously equilibrated with the mobile phase for 20 min. The spots were detected under UV light and using iodine vapours. The method enables rapid separation of clopidogrel enantiomers and can be successfully used in control of stereoselective synthesis of clopidogrel and in control of its purity. Finally, the molecular modelling of the inclusion complexes between the analytes and alpha-, beta-, and gamma-cyclodextrin was performed to investigate the mechanism of the enantiorecognition.", publisher = "Akademiai Kiado Rt, Budapest", journal = "Acta Chromatographica", title = "Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive", volume = "23", number = "2", pages = "235-245", doi = "10.1556/AChrom.23.2011.2.4" }
Antić, D., Filipić, S., Ivković, B., Nikolić, K.,& Agbaba, D.. (2011). Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive. in Acta Chromatographica Akademiai Kiado Rt, Budapest., 23(2), 235-245. https://doi.org/10.1556/AChrom.23.2011.2.4
Antić D, Filipić S, Ivković B, Nikolić K, Agbaba D. Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive. in Acta Chromatographica. 2011;23(2):235-245. doi:10.1556/AChrom.23.2011.2.4 .
Antić, Dušan, Filipić, Slavica, Ivković, Branka, Nikolić, Katarina, Agbaba, Danica, "Direct Separation of Clopidogrel Enantiomers by Reverse-Phase Planar Chromatography Method Using beta-Cyclodextrin as a Chiral Mobile Phase Additive" in Acta Chromatographica, 23, no. 2 (2011):235-245, https://doi.org/10.1556/AChrom.23.2011.2.4 . .