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Enantioseparation of aminoglutethimide and thalidomide by high performance liquid chromatography or supercritical fluid chromatography on mono‐2 and mono‐6‐O‐pentenyl‐β‐cyclodextrin‐based chiral stationary phases
Author(s) -
Duval Raphaël,
Lévêque Hubert,
Prigent Yann,
AboulEnein Hassan Y.
Publication year - 2001
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.62
Subject(s) - chemistry , supercritical fluid chromatography , thioether , enantiomer , chromatography , cyclodextrin , aminoglutethimide , high performance liquid chromatography , moiety , chiral column chromatography , sulfone , organic chemistry , medicine , cancer , breast cancer , aromatase
Abstract Mono‐2 and mono‐6‐ O ‐pentenyl‐β‐cyclodextrin (mono‐2‐pent‐β‐CD and mono‐6‐pent‐β‐CD), covalently linked to mercaptopropylsilica gel (thiol‐Si) through thioether or sulfone linkage, reveal differentiated enantioselectivities in the separation of piperidine‐2,6‐dione‐related drugs, namely aminoglutethimide and thalidomide, in supercritical fluid conditions. Supercritical fluid chromatographic resolution on completely defined mono‐cyclodextrin derivative‐based chiral stationary phases (CSP) is a method of choice for the separation of aminoglutethimide but not effective for thalidomide. For both high performance liquid chromatography (HPLC) and supercritical fluid chromatography (SFC) conditions, the impact of the position, imposed to be 2 or 6 in our synthetic pathway, of the pentenyl moiety on one of the glucopyranosidics of the CD cage is of crucial importance in the chiral discrimination phenomenon. Additionally, the nature of the heteroatom present in the spacer arm between the CD and the silica gel, in this case thioether or sulfone functionality, is also essential for the chiral recognition mechanism(s) for the solute enantiomer. Copyright© 2001 John Wiley & Sons, Ltd.