title: A family of single-isomer, dicationic cyclodextrin chiral selectors for capillary electrophoresis: mono-6(A)-ammonium-6(C)-butylimidazolium-β-cyclodextrin chlorides.
abstract: The first member of the single-isomer, dicationic cyclodextrin (CD) family, 6(A)-ammonium-6(C)-butylimidazolium-β-cyclodextrin chlorides (AMBIMCD), has been synthesized, analytically characterized, and used to separate a variety of acidic enantiomers and amino acids by CE. Starting from mono-6(A)-azido-β-cyclodextrin, the cationic imidazolium and ammonium moieties were subsequently introduced onto primary ring of β-cyclodextrin via nucleophilic addition and Staudinger reaction. The analytically pure AC regio-isomer CD was further obtained via column chromatography. This dicationic CD exhibited excellent enantioselectivities for selected analytes at concentration as low as 0.5 mM, which were even better than those of its mono-imidazolium or ammonium-substitued counterpart CDs at 10 equivalent concentrations. The effective mobilities of all studied analytes were found to decrease with the concentration of AMBIMCD. Inclusion complexation in combination with eletrostatic interactions seemed to account for the enhanced chiral discrimination process.
authors: Key Laboratory of Soft Chemistry and Functional Materials, Nanjing University of Science and Technology, Ministry of Education, Nanjing, PR China.
authors: Yun
authors: Y
authors: Dai
authors: Shuye
authors: S
authors: Wang
authors: Jie
authors: J
authors: Zhou
authors: Jian
authors: J
authors: Tang
authors: Weihua
authors: W
authors: Tang
mesh_terms: D000596:Amino Acids / Q000032:analysis / Q000737:chemistry; D002412:Cations; D002712:Chlorides / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D007536:Isomerism; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C583262:6(A)-ammonium-6(C)-butylimidazolium-beta-cyclodextrin; D000596:Amino Acids; D002412:Cations; D002712:Chlorides; D007093:Imidazoles; D000644:Quaternary Ammonium Compounds; D047392:beta-Cyclodextrins; C029899:imidazole