The separation of the enantiomers of diquats by capillary electrophoresis using randomly sulfated cyclodextrins as chiral selectors

0574336 - ÚOCHB 2024 RIV US eng J - Journal Article
Bílek, Jan - Koval, Dušan - Sázelová, Petra - Šolínová, Veronika - Severa, Lukáš - Reyes Gutierrez, Paul Eduardo - Teplý, Filip - Kašička, Václav
The separation of the enantiomers of diquats by capillary electrophoresis using randomly sulfated cyclodextrins as chiral selectors.
Journal of Separation Science. Roč. 46, č. 18 (2023), č. článku 2300417. ISSN 1615-9306. E-ISSN 1615-9314
R&D Projects: GA ČR(CZ) GA20-03899S
Institutional support: RVO:61388963
Keywords : capillary electrophoresis * chiral analysis * diquats * enantioseparation * sulfated cyclodextrins
OECD category: Analytical chemistry
Impact factor: 3.1, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/jssc.202300417

Diquats, derivatives of the widely used herbicide diquat, represent a new class of functional organic molecules. A combination of their special electrochemical properties and axial chirality could potentially result in their important applications in supramolecular chemistry, chiral catalysis, and chiral analysis. However, prior to their practical applications, the diquats have to be prepared in enantiomerically pure forms and the enantiomeric purity of their P- and M-isomers has to be checked. Hence, a chiral capillary electrophoresis (CE) method has been developed and applied for separation of P- and M-enantiomers of 11 new diquats. Fast and better than baseline CE separations of enantiomers of all 11 diquats within a short time 5–7 min were achieved using acidic buffer, 22 mM NaOH, 35 mM H3PO4, pH 2.5, as a background electrolyte, and 6 mM randomly sulfated α-, β-, and γ-cyclodextrins as chiral selectors. The most successful selector was sulfated γ-cyclodextrin, which baseline separated the enantiomers of all 11 diquats, followed by sulfated β-cyclodextrin and sulfated α-cyclodextrin, which baseline separated enantiomers of 10 and nine diquats, respectively. Using this method, a high enantiopurity degree of the isolated P- and M-enantiomers of three diquats with a defined absolute configuration was confirmed and their migration order was identified.
Permanent Link: https://hdl.handle.net/11104/0344679