Enantiomeric separation of furan derivatives and fused polycycles by cyclodextrin-modified micellar capillary electrophoresis

Abstract

The enantiomeric separations of highly hydrophobic furan derivatives and polycycles were performed and optimized using CD-modified micellar CE. The most effective chiral selector for the enantiomeric separation of these analytes was hydroxypropyl-gamma-CD. The effects of CD and SDS concentration and organic modifier were examined in order to optimize the separation conditions. The ratio of CD to surfactant concentration affected the enantiomeric separation significantly, with increases in the derivatized CD concentration generally enhancing resolution. Addition of an organic solvent modifier to the run buffer served to increase the analytes' solubility and enhance the separation efficiency. A highly acidic pH was necessary to effectively suppress the EOF when operating in the reverse polarity mode.

MEKC: An update focusing on practical aspects

“…Thus, CDs are used as pseudostationary complexing agents instead of SDS micelles in CD-mediated CZE [103][104][105] and also to provide analytes with an environment or a rather different mobility than negatively charged micelles in CD-mediated MEKC. A number of applications of CDs as modifiers in MEKC have been reported in recent years involving SDS micelles [106][107][108][109][110][111][112][113][114][115][116][117], and, less frequently, for mixed (SDS and sodium cholate) [118] and cationic micelles (TTAB) [119]; a detailed description of these applications is, however, beyond the scope of this review. Although chiral analysis in MEKC is usually done in the presence of CDs, some interesting alternatives have been proposed [120], one of which is based on the principles of enantioselective ligand exchange chromatography [121].…”

Experimental and computational study on the enantioseparation of four chiral fluoroquinolones by capillary electrophoresis with sulfated‐β‐cyclodextrin as chiral selector

“…2,27 It was speculated that the presence of aromatic rings in the vicinity of chiral center might be favorable to enantiomeric recognition due to the steric repulsion. 28 Four chiral FQs are similar in their basic molecular skeleton, but only OFLX has a chiral center close to its aromatic system, which could explain why OFLX enantiomers got the best resolution in the four FQs. For LMLX and GTLX, they shared the same chiral center and the enantiomeric resolutions of their enantiomers were also similar.…”

Chiral Separations

“…The effect of several experimental parameters in micellar capillary electrophoresis (MCE) was studied using a system of SDS and hydroxypropyl-β-CD as the chiral selector (71) as the model, with the first reported attempt of a computer simulation of the CD-SDS-MCE system. Enantioseparation of furan derivatives and fused polycycles were performed using CDmodified MCE (72), with the most effective chiral selector found to be γ-CD. The enantiomeric separation of hydrophobic dihydrofuroflavones were performed using hydroxypropyl-γ-CD by micellar CE (73).…”