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Estimation of racemization barriers of selected helquats and their derivatives by capillary electrophoresis using sulfated cyclodextrins as chiral selectors
Sázelová, Petra ; Koval, Dušan ; Severa, Lukáš ; Reyes Gutierrez, Paul Eduardo ; Jirásek, Michael ; Teplý, Filip ; Kašička, Václav
The recently developed capillary electrophoretic (CE) method for chiral analysis of helquats (helical N-heteroaromatic dications) was applied to monitoring of racemization of selected helquats and helquat styryl dyes and for the determination of their racemization barriers, i.e. activation Gibbs free energy deltaG≠. deltaG≠ of analyzed compounds was found to be in the range 107.7 – 115.7 kJ/mol.
Enantioseparations of drugs and catalysts by partial-filling affinity capillary electrophoresis using helquats as chiral selectors
Růžička, Martin ; Koval, Dušan ; Vávra, Jan ; Reyes Gutierrez, Paul Eduardo ; Teplý, Filip ; Kašička, Václav
Noncovalent molecular interactions between helquats, a new class of dicationic helical extended diquats and selected commonly used negatively charged chiral drugs and catalysts have been investigated using partial-filling affinity capillary electrophoresis (PF-ACE). Three types of interactions of analytes with helquats were observed: (1) medium strong enantioselective interactions, (2) medium strong non-enantioselective interactions and (3) no or very weak non-enantioselective interactions.
Chiral analysis of alfa-diimine Ru(II) and Fe(II) complexes by capillary electrophoresis using sulfated cyclodextrins as stereoselectors
Sázelová, Petra ; Koval, Dušan ; Severa, Lukáš ; Teplý, Filip ; Kašička, Václav
A fast and efficient capillary electrophoretic method was developed for enantioseparation of Ru(II) and Fe(II) polypyridyl complexes using anionic randomly sulfated alfa-, beta-, and gamma-cyclodextrins (S-alfa-CD, S-beta-CD, and S-gamma-CD) and their heptakis-(2,3-diacetyl-6-sulfato)-derivatives (Ac-S-alfa-CD, Ac-S-beta-CD, and Ac-S-gamma-CD) as chiral selectors. S-alfa-CD and S-gamma-CD were found to be the best chiral selectors providing high resolutions and short analysis times. The method was applied for the assessment of chiral purity of some batches of [Ru(bpy)3]2+ catalyst.
Capillary electrophoresis applied to chiral analysis of helquats and characterization of their intermediates and interconversion barriers using randomly and single isomer sulfated cyclodextrins as stereoselectors
Kašička, Václav ; Koval, Dušan ; Sázelová, Petra ; Severa, Lukáš ; Vávra, Jan ; Adriaenssens, Louis ; Sonawane, Manoj R. ; Teplý, Filip
Capillary electrophoresis in acidic sodium phosphate background electrolyte, pH 2.4, with randomly sulfated alfa-, beta- and gamma-cyclodextrins as chiral selectors was applied to fast, high-resolution separation of enantiomers of a series of 35 helquats, a new class of N-heteroaromatic dicationic helicene-like species. The developed methodology was employed for evaluation of preparative enantioresolution procedures of helquats, for monitoring their racemization and for determination of interconversion barrier of helquat enantiomers.
Capillary electrophoretic chiral analysis and estimation of helix inversion barrier of helquats using randomly sulfated cyclodextrins as chiral selectors
Kašička, Václav ; Koval, Dušan ; Sázelová, Petra ; Severa, Lukáš ; Adriaenssens, Louis ; Vávra, Jan ; Teplý, Filip
Capillary electrophoresis in acidic sodium phosphate background electrolyte, pH 2.4, with randomly sulfated alpha-, beta- and gamma-cyclodextrins as chiral selectors was employed for fast, high-resolution separation of enantiomers of a series of 24 helquats, a new class of N-heteroaromatic dicationic helicene-like species. The developed CE methodology will be utilized in the further investigation of helquats, e.g., in evaluation of their preparative enantioresolution procedures, in monitoring of their racemization and determination of interconversion barrier of helquat enantiomers.
Enantiomer separation and determination of helix inversion barrier of helical dications by capillary electrophoresis
Koval, Dušan ; Adriaenssens, Louis ; Severa, Lukáš ; Teplý, Filip ; Sázelová, Petra ; Kašička, Václav
Enantiomeric helical forms of dicationic helquats, a novel family of charged helicene-like molecules, have been separated by capillary electrophoresis (CE) using sodium-phosphate buffer, pH 2.5, as background electrolyte and sulfated beta- and gamma-cyclodextrins as chiral selectors. Additionally, CE was used to determine barrier to helix inversion of helquats.

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1 Teplý, František
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