Synthesis, analytical characterization and use of octakis(2,3-di-O-methyl-6-O-sulfo)-gamma-cyclodextrin, a novel, single-isomer, chiral resolving agent in low-pH background electrolytes.
The third member of the family of single-isomer, sulfated gamma-cyclodextrins, the sodium salt of octakis(2,3-di-O-methyl-6-O-sulfo)-gamma-cyclodextrin has been synthesized, analytically characterized and used for the capillary electrophoretic separation of the enantiomers of nonionic, weak acid and weak base analytes in low-pH aqueous background electrolytes. Though octakis(2,3-di-O-methyl-6-O-sulfo)-gamma-cyclodextrin complexes less strongly with many of the analytes tested than the other members of the single-isomer, 6-O-sulfo gamma-cyclodextrin family, such as octa(6-O-sulfo)-gamma-cyclodextrin and octakis(2,3-di-O-acetyl-6-O-sulfo)-gamma-cyclodextrin, it offers excellent separation selectivities, often complementary to those of both the single-isomer, 6-O-sulfo beta-cyclodextrins and 6-O-sulfo gamma-cyclodextrins. Rapid, efficient enantiomer separations were observed for a large number of structurally diverse analytes in acidic aqueous background electrolytes.
Busby
M Brent
MB
Department of Chemistry, Texas A & M University, College Station, TX 77842, USA.
Lim
Peniel
P
Vigh
Gyula
G
D003505:Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry; D004573:Electrolytes; D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D009930:Organic Chemicals / Q000302:isolation & purification; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins
D003505:Cyclodextrins; D004573:Electrolytes; D007202:Indicators and Reagents; D009930:Organic Chemicals; D047408:gamma-Cyclodextrins; C478758:octakis(2,3-dimethyl-6-O-sulfo)-gamma-cyclodextrin