CATIONIC BETA-CYCLODEXTRIN DERIVATIVE FOR CHIRAL SEPARATIONS

A novel hepta-substituted beta-cyclodextrin bearing the methoxyethylam ine group linked to the upper cyclodextrin rim was successfully used a s a chiral selector for enantiomeric separation of non-steroidal anti- inflammatory drugs (NSAIDs) and phenoxypropionic acid herbicides (PPAH s). Separation parameters such as pH and concentration were found to h ave major influences on enantiomeric resolution of the NSAIDs and PPAH s. Results indicate that kis(6-methoxyethylamine-6-deoxy)-beta-cyclode xtrin [beta-CD-OMe (VII)] performs exceptionally well for the enantiom eric resolution of NSAIDs: indoprofen and fenoprofen (R-s=11 and 14, r espectively). In addition, baseline enantiomeric separation of a mixtu re of six pairs of PPAHs was achieved in under 30 min. Compared to oth er cationic beta-cyclodextrins reported in the literature, the beta-CD -OMe (VII) showed improved selectivity for both classes of the aforeme ntioned anionic racemates. (C) 1998 Elsevier Science B.V.