Synthesis of mono‐6‐deoxy‐6‐N,N,N′,N′,N′‐pentamethylethylenediammonio‐cyclomaltoheptaose, a single‐isomer, monosubstituted, permanently dicationic β‐CD and its use for enantiomer separations by CE

Abstract

The dichloride salt of mono-6-deoxy-6-N,N,N',N',N'-pentamethylethylenediammonio-cyclomaltoheptaose (PEMEDA-BCD), the first single-isomer, monosubstituted, permanently dicationic beta-CD has been synthesized, analytically characterized, and used for the capillary electrophoretic separation of the enantiomers of a group of analytes in acidic and basic BGEs. When the concentration of PEMEDA-BCD was changed in the BGEs, the resulting effective mobilities of the analytes and the respective separation selectivities followed the predictions of the ionic strength-corrected charged resolving agent migration model. Good separation selectivities and favorable normalized EOF mobilities allowed for the rapid, efficient separation of the enantiomers of anionic, weak acid and nonionic analytes in the low- and/or high-pH BGEs.

Advanced CE for chiral analysis of drugs, metabolites, and biomarkers in biological samples

“…Therefore, it is not surprising that even in the field of newly developed chiral selectors novel CD derivatives prevail significantly [104]. The preparation of selectively substituted derivatives [102,112] is preferred as this eliminates the creation of mixtures of CDs having different substitution patterns, and, by that, different complexing properties (difficulties with separation reproducibility) [113][114][115]. Several different groups of CD derivatives can be distinguished, namely, (i) neutral CDs, (ii) negatively and positively charged CDs, (iii) amphoteric CDs, and (iv) polymerized CDs.…”

Cyclodextrins in capillary electrophoresis enantioseparations – Recent developments and applications

“…Vigh's group developed a single isomer, monosubstituted, permanently doubly positively charged b-CD derivative, mono-6-deoxy-6-N,N,N9,N9,N9-pentamethylethyldiammonio-b-CD (PEMEDA-b-CD) [55]. The rationale behind the development of this CD was the fact that commercially available single isomer positively charged CDs are typically monosubstituted, thus bearing a single positive charge.…”

Chiral Separations by Capillary Electrophoresis

“…Some recent applications with positively charged CD derivatives have been reported [59][60][61]. In [59], 6-O-(2-OH-3-trimethylammoninopropyl)-β-CD was synthesized and applied for the separation of 11 acidic analytes.…”

“…In analogy with the anionic single isomer CD, Vigh's group [60] synthesized mono-6-deoxy-6-N,N,N ,N ,N -pentamethylethylenediaminocyclomaltoheptaose, a permanently dicationic derivative of β-CD. The CD proved to be very useful for the analysis of negatively charged analytes (i.e., weak acids at high pH and O-sulfated analytes at low pH).…”