title: Quantitative prediction of enantioseparation using β-cyclodextrin derivatives as chiral selectors in capillary electrophoresis.
abstract: β-Cyclodextrin derivatives as chiral selectors are becoming increasingly important for enantioseparations in capillary electrophoresis (CE). Nevertheless, there are some enormous challenges in choosing effective selectors from a variety of compounds, and up to now no systematic quantitative studies for predicting the possibility of enantiomeric separation before CE experiments have been reported. In this paper, in order to resolve previous confusions, we investigated the enantioseparations of ten chiral drugs using a method of combining experiments with theoretical calculations. MMFF, PM3, DFT and ONIOM2 methods were simultaneously utilized during the course of our computer simulations. The results indicated that a specific value of greater than or approximately equal to 6 kJ mol(-1) for the interaction energy difference (ΔΔE) between a pair of enantiomers with a selector is required in order to achieve enantiomeric separation. This discovery offers a meaningful reference to predict enantiomeric separations, so as to design and synthesize some more efficient chiral selectors.
authors.affiliation: Key Laboratory of Structure-Based Drug Design and Discovery, Shenyang Pharmaceutical University, Ministry of Education, Wenhua Road 103, Shenyang 110016, P. R. China. suntiemin@126.com.
authors.forename: Xin
authors.initials: X
authors.lastname: Guo
authors.forename: Zhiqiang
authors.initials: Z
authors.lastname: Wang
authors.forename: Lihua
authors.initials: L
authors.lastname: Zuo
authors.forename: Zhixu
authors.initials: Z
authors.lastname: Zhou
authors.forename: Xingjie
authors.initials: X
authors.lastname: Guo
authors.forename: Tiemin
authors.initials: T
authors.lastname: Sun
mesh_terms: D003198:Computer Simulation; D019075:Electrophoresis, Capillary / Q000379:methods*; D008956:Models, Chemical; D008958:Models, Molecular; D004364:Pharmaceutical Preparations / Q000737:chemistry / Q000302:isolation & purification*; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
chemical_list: D004364:Pharmaceutical Preparations; D047392:beta-Cyclodextrins; C031215:betadex