title: Mono-6A-(4-methoxybutylamino)-6A-β-cyclodextrin as a chiral selector for enantiomeric separation.
abstract: A new member of the family of methoxylalkylamino monosubstituted β-cyclodextrins, mono-6(A)-(4-methoxybutylamino)-6(A)-β-cyclodextrin, has been developed as a chiral selector for enantioseparation in capillary electrophoresis. This amino cyclodextrin exhibited good enantioselectivities for 16 model acidic racemates including three dansyl amino acids at an optimum pH of 6.0. Excellent chiral resolutions over six were obtained for α-hydroxy acids and 2-phenoxypropionic acids with 3.0 mM chiral selector. The good chiral recognition for α-hydroxyl acids was attributed to inclusion complexation, electrostatic interactions, and hydrogen bonding. The hydrogen-bonding-enhanced chiral recognition was revealed by NMR spectroscopy. The chiral separation of acidic racemates was further improved with the addition of methanol (≤10 vol%) as an organic additive.
authors.affiliation: School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing, People's Republic of China.
authors.forename: Shuye
authors.initials: S
authors.lastname: Wang
authors.forename: Yiying
authors.initials: Y
authors.lastname: Wang
authors.forename: Jie
authors.initials: J
authors.lastname: Zhou
authors.forename: Yingying
authors.initials: Y
authors.lastname: Lu
authors.forename: Jian
authors.initials: J
authors.lastname: Tang
authors.forename: Weihua
authors.initials: W
authors.lastname: Tang
mesh_terms: D000596:Amino Acids / Q000737:chemistry* / Q000302:isolation & purification; D019075:Electrophoresis, Capillary / Q000295:instrumentation* / Q000379:methods; D006860:Hydrogen Bonding; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D047392:beta-Cyclodextrins; C031215:betadex
keywords: Capillary electrophoresis; Chiral separation; Enantiomers; Single-isomer cyclodextrins