Synthesis and application of a novel single-isomer mono-6-deoxy-6-(3R,4R-dihydroxypyrrolidine)-beta-cyclodextrin chloride as a chiral selector in capillary electrophoresis.
A novel positively charged single-isomer of beta-cyclodextrin, mono-6-deoxy-6-(3R,4R-dihydroxypyrrolidine)-beta-CD chloride (dhypy-CDCl), was synthesized and employed as a chiral selector for the first time in capillary electrophoresis (CE) for the enantioseparation of anionic and ampholytic acids. The effects of the running buffer pH, chiral selector concentration, analyte structure and organic modifier on the enantioseparation were studied in detail. The chiral selectivity and resolution for most of the studied analytes decreased as the buffer pH increased in the range of 6.0-9.0. Increasing selector concentration led to decreased effective mobility, increased chiral selectivity and resolution for most of the studied analytes. Moreover, the hydroxyl groups located on the dihydroxypyrrolidine substituent of the dhypy-CDCl could have influence on the chiral separation.
Xiao
Yin
Y
School of Chemical & Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, Singapore 637459, Singapore.
Ong
Teng-Teng
TT
Tan
Timothy Thatt Yang
TT
Ng
Siu-Choon
SC
D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry*; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D047392:beta-Cyclodextrins / Q000138:chemical synthesis* / Q000737:chemistry*
D011759:Pyrrolidines; D047392:beta-Cyclodextrins; C540477:mono-6-deoxy-6-(3R,4R-dihydroxypyrrolidine)-beta-cyclodextrin chloride