"Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography.
This communication reports the preparation of two new cyclodextrin (CD) chiral stationary phases (CSPs): heptakis(6-deoxy-6-azido)-β-CD and heptakis(6-deoxy-6-azido-phenylcarbamoylated)-β-CD CSPs that perform quite differently to our previously reported "click" immobilized CD-CSPs. These CSPs are sterically congested at the narrow mouth of the CD and exhibit chiral discrimination between over 40 pairs of enantiomers in high performance liquid chromatography. The free hydroxyl CSP afforded better separation of indoprofen, ketoprofen, Tröger's base, hydroxyl, carboxylic and dansyl amino acids than did the phenylcarbamoylated CSP, while the latter was better at resolving aryl alcohols, flavonoids, β-blockers and β-agonists. The current work shows that enantiodiscrimination achieved with different CSPs for different classes of analyte may be correlated with CD accessibility and peripheral functionality.
School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore, Singapore.
Yong
Y
Wang
David James
DJ
Young
Timothy Thatt Yang
TT
Tan
Siu-Choon
SC
Ng
D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D057930:Click Chemistry / Q000379:methods*; D009930:Organic Chemicals / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000737:chemistry*
D009930:Organic Chemicals; D047392:beta-Cyclodextrins