Cationic beta-cyclodextrin derivative for chiral separations.
A novel hepta-substituted beta-cyclodextrin bearing the methoxyethylamine group linked to the upper cyclodextrin rim was successfully used as a chiral selector for enantiomeric separation of non-steroidal anti-inflammatory drugs (NSAIDs) and phenoxypropionic acid herbicides (PPAHs). Separation parameters such as pH and concentration were found to have major influences on enantiomeric resolution of the NSAIDs and PPAHs. Results indicate that heptakis(6-methoxyethylamine-6-deoxy)-beta-cyclodextrin [beta-CD-OMe (VII)] performs exceptionally well for the enantiomeric resolution of NSAIDs: indoprofen and fenoprofen (Rs = 11 and 14, respectively). In addition, baseline enantiomeric separation of a mixture of six pairs of PPAHs was achieved in under 30 min. Compared to other cationic beta-cyclodextrins reported in the literature, the beta-CD-OMe (VII) showed improved selectivity for both classes of the aforementioned anionic racemates.
Haynes
J L
JL
Department of Chemistry, Louisiana State University, Baton Rouge 70820, USA.
Shamsi
S A
SA
O'Keefe
F
F
Darcey
R
R
Warner
I M
IM
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000302:isolation & purification; D003505:Cyclodextrins / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D006540:Herbicides / Q000737:chemistry* / Q000302:isolation & purification; D006863:Hydrogen-Ion Concentration; D009994:Osmolar Concentration; D011422:Propionates / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D000894:Anti-Inflammatory Agents, Non-Steroidal; D003505:Cyclodextrins; D006540:Herbicides; D011422:Propionates; C029658:propionic acid