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Synthesis of charged cyclodextrin highly soluble in organic solvents for enantiomer separations in capillary electrophoresis

Omar Maldonado

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Abstract

Synthesis of charged cyclodextrin highly soluble in organic solvents was\nmade by exchanging the inorganic counter ion (Na+) of heptakis (2,3-di-Omethyl-\n6-O-sulfo)-β-CD (Na7HDMS) with tetrabutylammonium (TBA+), to\nproduce TBA7HDMS. The same ion exchange was used to synthesize the TBA\nsalts of the analogous CDs TBA6HxDMS and TBA8ODMS. Indirect-UV\ndetection capillary electrophoresis (CE) and 1H NMR were used as the\ncharacterization methods.\nSeparations of thirteen pharmaceuticals were made using TBA7HDMS as\nthe chiral resolving agent in aqueous CE. On the other hand, a set of twenty\npharmaceuticals was used for the enantiomer separations in non-aqueous CE\n(NACE). Comparison between the results obtained with TBA7HDMS in aqueous\nand non-aqueous CE were made. In addition, comparison between the results\nobtained with TBA7HDMS and Na7HDMS in aqueous and non-aqueous CE were\nmade as well.

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Synthesis of charged cyclodextrin highly soluble in organic solvents was\nmade by exchanging the inorganic counter ion (Na+) of heptakis (2,3-di-Omethyl-\n6-O-sulfo)-β-CD (Na7HDMS) with tetrabutylammonium (TBA+), to\nproduce TBA7HDMS. The same ion exchange was used to synthesize the TBA\nsalts of the analogous CDs TBA6HxDMS and TBA8ODMS. Indirect-UV\ndetection capillary electrophoresis (CE) and 1H NMR were used as the\ncharacterization methods.\nSeparations of thirteen pharmaceuticals were made using TBA7HDMS as\nthe chiral resolving agent in aqueous CE. On the other hand, a set of twenty\npharmaceuticals was used for the enantiomer separations in non-aqueous CE\n(NACE). Comparison between the results obtained with TBA7HDMS in aqueous\nand non-aqueous CE were made. In addition, comparison between the results\nobtained with TBA7HDMS and Na7HDMS in aqueous and non-aqueous CE were\nmade as well.

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Available abstract

Synthesis of charged cyclodextrin highly soluble in organic solvents was\nmade by exchanging the inorganic counter ion (Na+) of heptakis (2,3-di-Omethyl-\n6-O-sulfo)-β-CD (Na7HDMS) with tetrabutylammonium (TBA+), to\nproduce TBA7HDMS. The same ion exchange was used to synthesize the TBA\nsalts of the analogous CDs TBA6HxDMS and TBA8ODMS. Indirect-UV\ndetection capillary electrophoresis (CE) and 1H NMR were used as the\ncharacterization methods.\nSeparations of thirteen pharmaceuticals were made using TBA7HDMS as\nthe chiral resolving agent in aqueous CE. On the other hand, a set of twenty\npharmaceuticals was used for the enantiomer separations in non-aqueous CE\n(NACE). Comparison between the results obtained with TBA7HDMS in aqueous\nand non-aqueous CE were made. In addition, comparison between the results\nobtained with TBA7HDMS and Na7HDMS in aqueous and non-aqueous CE were\nmade as well.

Key concepts: Capillary electrophoresis, Chemistry, Aqueous solution, Enantiomer, Cyclodextrin, Electrophoresis, Chromatography, Organic chemistry

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