"Click" immobilized perphenylcarbamated and permethylated cyclodextrin stationary phases for chiral high-performance liquid chromatography application.
Two cyclodextrin-based chiral stationary phases have been prepared by immobilization of functionalized mono-6-azido-beta-CD derivatives to alkynyl modified silica via "click" chemistry and applied to the HPLC enantioseparation of various chiral compounds. The perphenylcarbamated CD CSP (CCP-CSP) exhibited excellent chiral recognition of a wide range of analytes including racemic aryl alcohols, flavonoids, bendroflumethiazide, atropine and some beta-blockers. Methanol proved to be a better organic modifier than acetonitrile for most of the analytes with the exception of bendroflumethiazide. The "click" chemistry immobilized permethylated CD CSP (CCM-CSP) afforded poor chiral recognition for most analytes, but could resolve non-aromatic ionone derivatives which were not separated on CCP-CSP. These results suggest that resolution with cyclodextrin derived CSPs depend on a complex interplay of 'host'-'guest' inclusion, hydrogen bonding, pi-pi and hydrophobic interactions.
Wang
Yong
Y
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore.
Young
David J
DJ
Tan
Timothy Thatt Yang
TT
Ng
Siu-Choon
SC
D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation*; D003505:Cyclodextrins / Q000737:chemistry*; D006860:Hydrogen Bonding
D003505:Cyclodextrins