Enantioseparation of a novel “click” chemistry derived native β-cyclodextrin chiral stationary phase for high-performance liquid chromatography

• Published in: Journal of Chromatography A 2009-03, Vol.1216 (12), p.2388-2393
• Main Authors: Wang, Yong, Ong, Teng-Teng, Li, Lai-Sheng, Tan, Timothy Thatt Yang, Ng, Siu-Choon
• Format: Article
• Language: English
• Subjects: Analysis; Analytical chemistry; Biological and medical sciences; Chemistry; Chiral stationary phases; Chromatographic methods and physical methods associated with chromatography; Click chemistry; Dns-amino acids; Enantioseparation; Exact sciences and technology; General pharmacology; Medical sciences; Native β-cyclodextrin; Other chromatographic methods; Pharmacology. Drug treatments
• ISSN: 0021-9673
• DOI: 10.1016/j.chroma.2009.01.039

A novel native β-cyclodextrin chiral stationary phase was prepared via “click” chemistry with cuprous iodide–triphenylphosphine complex as the catalyst and applied for enantioseparation of Dns-amino acids, substituted phenyl and phenoxy group modified propionic acids, flavonoids, and some pharmaceutical compounds such as nimodipine, propranolol, brompheniramine and bendroflumethiazide in reversed-phase high-performance liquid chromatography. The studied analytes could be resolved under different separation conditions. The resolution of Dns-DL-Leu could reach 5.08 using a mobile phase consisting of 1% (w/w) triethylammonium acetate buffer (pH 4.11) and methanol (50:50 v/v). The effects of buffer pH and the content of organic modifier on enantioseparation of Dns-amino acids by this novel chiral phase were being investigated. The separation results demonstrate that click chemistry, a versatile reaction, affords a facile approach towards the preparation of stable chiral stationary phases.