title: Preparation of a novel cyclodextrin derivative of benzimido-β-cyclodextrin and its enantioseparation performance in HPLC.
abstract: A novel cyclodextrin (CD) derivative, mono-6-deoxy-benzimide-β-CD (MB-β-CD), in which a rigid substituent was linked to the narrow edge of the CD with a flexible H(2)C-N group, was successfully synthesized through the condensation of mono-6-deoxy-6-amino-β-cyclodextrin and benzaldehyde. To evaluate its enantioseparation abilities and investigate the role of the CD substituents and linkage in chiral recognition, MB-β-CD and mono-6-deoxyphenylimine-β-CD (MP-β-CD) with a rigid linkage were compared in the separation of 36 chiral compounds in a methanol/water mobile phase. The separation results showed that most of the analytes with rigid structures afforded better enantioresolutions on the MP-β-CD (with a rigid linkage) chiral stationary phase (CSP), while better enantioseparations for analytes with flexible structures and big steric hindrance were obtained on the MB-β-CD (with a flexible linkage) CSP. The former exhibited a specificity for the analyte structures, while the latter was more adaptable. Molecular dynamics simulations were performed to further understand the discrimination process and the function of the CD side arm.
authors: R&D Center for Pharmaceuticals, School of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing 100081, China.
authors: Xia
authors: X
authors: Li
authors: Zhiming
authors: Z
authors: Zhou
authors: Wenhong
authors: W
authors: Zhou
authors: Li
authors: L
authors: Dai
authors: Zhihuai
authors: Z
authors: Li
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003505:Cyclodextrins / Q000032:analysis* / Q000138:chemical synthesis*; D056004:Molecular Dynamics Simulation; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000032:analysis / Q000138:chemical synthesis
chemical_list: D003505:Cyclodextrins; D047392:beta-Cyclodextrins; C572214:mono-6-deoxy-benzimide-beta-cyclodextrin