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Synthesis, analytical characterization and use of octakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)‐γ‐cyclodextrin, a novel, single‐isomer, chiral resolving agent in low‐pH background electrolytes
Author(s) -
Busby M. Brent,
Lim Peniel,
Vigh Gyula
Publication year - 2003
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.200390045
Subject(s) - cyclodextrin , chemistry , aqueous solution , enantiomer , electrolyte , analyte , combinatorial chemistry , stereochemistry , organic chemistry , chromatography , electrode
The third member of the family of single‐isomer, sulfated γ‐cyclodextrins, the sodium salt of octakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)‐γ‐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)‐γ‐cyclodextrin complexes less strongly with many of the analytes tested than the other members of the single‐isomer, 6‐ O ‐sulfo γ‐cyclodextrin family, such as octa(6‐ O ‐sulfo)‐γ‐cyclodextrin and octakis(2,3‐di‐ O ‐acetyl‐6‐ O ‐sulfo)‐γ‐cyclodextrin, it offers excellent separation selectivities, often complementary to those of both the single‐isomer, 6‐ O ‐sulfo β‐cyclodextrins and 6‐ O ‐sulfo γ‐cyclodextrins. Rapid, efficient enantiomer separations were observed for a large number of structurally diverse analytes in acidic aqueous background electrolytes.