Non-aqueous, capillary electrophoretic separations of enantiomers with a charged cyclodextrin highly-soluble in organic solvents

Date

2005-11-01

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Publisher

Texas A&M University

Abstract

The synthesis of the sodium salt of heptakis (2, 3-di-O-acetyl-6-O-sulfo)-β-cyclodextrin was modified to increase the isomeric purity to 98.5%. This salt was used to obtain the organic-solvent-soluble, single-isomer, charged tetrabutylammonium salt of heptakis (2, 3-di-O-acetyl-6-O-sulfo)-β-cyclodextrin. Its isomeric purity was higher than 99%, as determined by CE, and its structure was confirmed by NMR and ESI-MS analysis. The hydrophobic single-isomer cyclodextrin was utilized to separate the enantiomers of weak base analytes in aprotic media by capillary electrophoresis. The effective mobilities and separation selectivities follow trends observed with negatively charged cyclodextrins in amphiprotic solvents. The properties of the dissolved cyclodextrin are altered by its counter ion, thereby affecting the separations of enantiomers. The aprotic media allow the modification of the separation selectivity, since the binding strength of the enantiomers to the cyclodextrin is intermediate between that reported in aqueous and methanolic buffers.

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