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Synthesis, Analytical Characterization and Initial Capillary Electrophoretic Use in an Acidic Background Electrolyte of a New, Single-Isomer Chiral Resolving Agent: heptakis(2-O-sulfo-3-O-methyl-6-O-acetyl)-β-cyclodextrin

Synthesis, Analytical Characterization and Initial Capillary Electrophoretic Use in an Acidic Background Electrolyte of a New, Single-Isomer Chiral Resolving Agent: heptakis(2-O-sulfo-3-O-methyl-6-O-acetyl)-β-cyclodextrin

Edward Tutu, Gyula Vigh

Electrophoresis. 2011 Oct;32(19):2655-62.

PMID: 21983817

Abstract:

The sodium salt of heptakis(2-O-sulfo-3-O-methyl-6-O-acetyl)cyclomaltoheptaose (HAMS), the first single-isomer sulfated β-CD that carries the sulfo group exclusively at the C2 position, has been synthesized. The purity of each synthetic intermediate and of the final product was determined by hydrophilic interaction (HILIC) and reversed-phase HPLC. The structural identity of each intermediate and of the final product was verified by 1-D and 2-D NMR spectroscopy and MALDI-TOF MS. HAMS was used for the capillary electrophoretic separation of the enantiomers of a set of non-ionic and weak base analytes in pH 2.5 background electrolytes. Rapid separations with satisfactory peak resolution values were obtained for most enantiomers using low concentrations of HAMS. The effective mobilities and separation selectivities were dependent on the concentration of HAMS according to the predictions of the charged resolving agent migration model. The separation selectivities observed with HAMS, heptakis(2-O-methyl-3-O-acetyl-6-O-sulfo)cyclomaltoheptaose and heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomaltoheptaose were different for some of the analytes studied in detail.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP37191698	β-Cyclodextrin, sulfated sodium salt		37191-69-8	Price
LS741340	Acetyl-β-cyclodextrin			Price

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