Synthesis and applications of sulfopropyl ether γ-cyclodextrin polymer as chiral selector in capillary electrophoresis

Abstract

A novel sulfopropyl ether γ-cyclodextrin polymer (SPE-γ-CDP) through polycondensating sulfated cyclodextrins (SCDs) was synthesized. This synthesis approach also has the potential of preparing other derived cyclodextrins (CDs) polymers. The polymerized SCDs took on both the properties of SCDs and certain characteristics of polymers, such as chiral selectivity and high viscosity. Synthesis parameters, including reactions sequence, sulfation, and polycondensation conditions were investigated systematically. The product was characterized by elemental analysis, infrared spectroscopy (IR), and indirect UV detections prior to use as background electrolytes additive. The separation conditions, including the concentration of SPE-γ-CDP, the concentration and pH of running buffer, separation voltage, as well as the additional organic solution were optimized during chiral separation of neutral, acidic, and basic enantiomers in capillary electrophoresis (CE). SPE-γ-CDP was proven to be an effective chiral resolving agent in CE with the advantages of simple synthesis process, low cost, similar ratio of charge-to-mass, low current, great reproducibility, and reusability. Graphical Abstract Synthesis and applications of sulfopropyl ether γ-cyclodextrin polymer.

Chiral selectors in CE: Recent development and applications (mid‐2014 to mid‐2016)

“…In comparison to the two previously described studies [68,76], where the separation of promethazine was performed by the use of negatively charged CDs, it can be concluded that the best enantioseparation was achieved when HS-␤-CD was used (R S = 3.2) [68]. SPE-␥ -CDP and per(6-sulfo-deoxy)-␤-CD, under the optimum separation conditions used in each study, provided a similar separation with resolution values of 1.82 and 2.0, respectively [76,77]. 2,3-Diacetyl-6-sulfo-derived CD is an alternative negatively charged CD, which has over the last few years been used as a CS in CE [22,23].…”

“…Sulfopropyl ether γ‐CD (SPE‐γ‐CD) is a different sulfur‐CD derivative that was synthesized and applied as a CS in CE . After the characterization of SPE‐γ‐CD polymer (SPE‐γ‐CDP), its enantioseparation ability was evaluated for the separation of promethazine, warfarin, and verapamil enantiomers, and it was compared to SPE‐γ‐CD and γ‐CD polymer (γ‐CDP).…”