The empirical comparison of cyclofructans and cyclodextrins as chiral selectors in capillary electrophoretic separation of atropisomers of R,S‐1,1’‐binaphthalene‐2,2’‐diyl hydrogen phosphate

Abstract

Native cyclofructans and their isopropyl derivatives were studied as chiral selectors in capillary electrophoresis and compared with α- and β-cyclodextrin. R,S-1,1'-Binaphthalene-2,2'-diyl hydrogen phosphate was used as a model chiral compound. The empirical observation of the enantioselectivity of native cyclofructans and isopropyl derivatives of cyclofructans was described and compared with the cyclodextrins. The influence of methanol and acetonitrile, as the most commonly used organic solvents, and sodium dodecyl sulfate as a micelle forming additive on the separation of R,S-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate atropisomers was achieved. The different enantiorecognition abilities resulting from unlike interaction mechanism with R,S-1,1'-binaphthalene-2,2'-diyl hydrogen phosphate were observed for the studied cyclodextrins and cyclofructans, especially when methanol or sodium dodecyl sulfate were used as modifiers of the separation conditions.

Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers

“…In this review, new applications, covering years 2010–2016, are described and discussed with a specific focus on current topics and trends concerning HPLC enantioseparations. Indeed, despite electromigration techniques have been shown to be a powerful tool also for atropisomers separation , HPLC is still the most commonly used technique due to its widespread popularity. At the same time, supercritical fluid chromatography (SFC) has been developed both for analytical and preparative purposes, receiving special attention by pharmaceutical industry and becoming the preferred technique for enantioseparation and purification in drug discovery research.…”

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

“…Recently, CFs and CDs have been used as CSs for the separation of BHP . It was observed that for an effective enantioseparation, higher concentrations of CFs were required than of CDs.…”

Fast separation of enantiomers by capillary electrophoresis using a combination of two capillaries with different internal diameters

“…The macrocyclic oligosaccharides, cyclofructans (CFs), are the next promising chiral selectors for CE. They consist of six or more β‐2,1‐linked D‐fructofuranose units with 18‐crown‐6 ether core . These chiral selectors and their derivatives have been shown to separate a wide range of chiral compounds by HPLC, SFC as well as CE .…”