Synthesis of a single-isomer sulfated beta-cyclodextrin carrying nonidentical substituents at all of the C2, C3, and C6 positions and its use for the electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes. Part 2: Heptakis(2-O-methyl-6-O-sulfo) cyclomaltoheptaose.
The sodium salt of heptakis(2-O-methyl-6-O-sulfo)cyclomaltoheptaose (HMS), the second single-isomer, sulfated beta-CD 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 23 weak base analytes in acidic aqueous and methanolic BGEs. HMS interacted strongly with only about half of the analytes studied. The good separation selectivities and favorable normalized EOF mobilities allowed for rapid, efficient separation of the enantiomers of 19 of the 23 weak base analytes in the aqueous BGEs, often with separation selectivity values complimentary to those obtained with other single-isomer sulfated CDs. HMS did not prove to be as good a resolving agent in acidic methanolic BGEs as its counterpart, heptakis(2-O-methyl-3-O-acetyl-6-O-sulfo)cyclomaltoheptaose.
Busby
M Brent
MB
Department of Chemistry, Texas A&M University, College Station, TX, USA.
Vigh
Gyula
G
D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D000432:Methanol; D012997:Solvents; D013237:Stereoisomerism; D013431:Sulfates; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry
D012997:Solvents; D013431:Sulfates; D047392:beta-Cyclodextrins; C507311:heptakis(2-O-methyl-6-O-sulfo)cyclomaltoheptaose; D000432:Methanol