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Single‐isomer sulfated α‐cyclodextrins for capillary electrophoresis: Hexakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)‐α‐cyclodextrin, synthesis, analytical characterization, and initial screening tests
Author(s) -
Li Shulan,
Vigh Gyula
Publication year - 2004
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.200405839
Subject(s) - chemistry , capillary electrophoresis , cyclodextrin , enantiomer , analyte , sulfation , electrolyte , ring (chemistry) , sodium , medicinal chemistry , stereochemistry , chromatography , organic chemistry , biochemistry , electrode
The third, concluding member of the family of single‐isomer, fully sulfated α‐cyclodextrins, the sodium salt of hexakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)‐α‐cyclodextrin (HxDMS), has been synthesized on the kilogram scale, completing the nine‐member array of the single‐isomer, 6‐ O ‐sulfo CDs now available. HxDMS was tested for the capillary electrophoretic (CE) resolution of the enantiomers of nonelectrolyte, weak acid and weak base analytes contained in our CD screening kit. HxDMS complexed differently with many of the analytes tested than either its larger‐ring analogs, heptakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)‐β‐CD (HDMS) and octakis(2,3‐di‐ O ‐methyl‐6‐ O ‐sulfo)‐γ‐CD (ODMS) or its same‐ring, but differently substituted analogs, hexakis(6‐ O ‐sulfo)‐α‐CD (HxS) and hexakis(2,3‐di‐ O ‐acetyl‐6‐ O ‐sulfo)‐α‐CD (HxDAS). For all analytes, the effective mobilities and separation selectivities as a function of the background electrolyte concentration of HxDMS followed the trends that were found for the other single‐isomer, 6‐ O ‐sulfo CDs.