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Synthesis of heptakis(2‐ O ‐methyl‐3‐ O ‐acetyl‐6‐ O ‐sulfo)‐cyclomaltoheptaose, a single‐isomer, sulfated β‐cyclodextrin carrying nonidentical substitutents at all the C2, C3, and C6 positions and its use for the capillary electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes
Author(s) -
Busby M. Brent,
Vigh Gyula
Publication year - 2005
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.200500057
Subject(s) - chemistry , cyclodextrin , aqueous solution , electrolyte , enantiomer , sulfation , capillary electrophoresis , ionic liquid , base (topology) , analyte , weak base , sodium , chromatography , medicinal chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , mathematical analysis , mathematics , electrode
The sodium salt of heptakis(2‐ O ‐methyl‐3‐ O ‐acetyl‐6‐ O ‐sulfo)cyclomaltoheptaose (HMAS), the first single‐isomer, sulfated β‐cyclodextrin carrying nonidentical substituents at all of the C2, C3, and C6 positions, has been synthesized, analytically characterized, and used for the capillary electrophoretic separation of the enantiomers of a group of 24 weak base pharmaceuticals in acidic aqueous and acidic methanolic background electrolytes. HMAS interacted more strongly with most of the analytes studied than heptakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)cyclomaltoheptaose, but less strongly than heptakis(2,3‐di‐ O ‐acetyl‐6‐ O ‐sulfo)cyclomaltoheptaose, the respective analogs with identical substituents at the C2 and C3 positions. The good separation selectivities and favorable normalized electroosmotic flow mobilities allowed for rapid, efficient separation of the enantiomers of 19 of the 24 weak base analytes in the aqueous and methanolic background electrolytes. The trends in the effective mobilities and separation selectivities as a function of the HMAS concentration closely followed the predictions of the ionic strength‐corrected charged resolving agent migration model.