New single isomer negatively charged β-cyclodextrin derivatives as chiral selectors in capillary electrophoresis

2013 ◽  
Vol 34 (8) ◽  
pp. 1232-1240 ◽  
Author(s):  
Jutima Boonleang ◽  
John F. Stobaugh
Keyword(s):  
Capillary Electrophoresis ◽  
Cyclodextrin Derivatives ◽  
Chiral Selectors ◽  
Single Isomer

Chiral capillary electrophoresis with cationic pyrrolidinium-β-cyclodextrin derivatives as chiral selectors

2010 ◽  
Vol 33 (12) ◽  
pp. 1797-1805 ◽  
Author(s):  
Yin Xiao ◽  
Yong Wang ◽  
Teng-Teng Ong ◽  
Liya Ge ◽  
Swee Ngin Tan ◽  
...  
Keyword(s):  
Capillary Electrophoresis ◽  
Cyclodextrin Derivatives ◽  
Chiral Selectors ◽  
Chiral Capillary Electrophoresis

scholarly journals Single isomer cyclodextrins as chiral selectors in capillary electrophoresis

2020 ◽  
Vol 1627 ◽  
pp. 461375
Author(s):  
Ida Fejős ◽  
Eszter Kalydi ◽  
Milo Malanga ◽  
Gábor Benkovics ◽  
Szabolcs Béni
Keyword(s):  
Capillary Electrophoresis ◽  
Chiral Selectors ◽  
Single Isomer

scholarly journals Single Isomer N-Heterocyclic Cyclodextrin Derivatives as Chiral Selectors in Capillary Electrophoresis

Molecules ◽  
2021 ◽  
Vol 26 (17) ◽  
pp. 5271
Author(s):  
Ida Fejős ◽  
Eszter Kalydi ◽  
Edit Luca Kukk ◽  
Mimimorena Seggio ◽  
Milo Malanga ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Cyclodextrin Derivatives ◽  
Ph Titration ◽  
Chiral Selectors ◽  
Single Isomer ◽  
1H Nuclear Magnetic Resonance ◽  
Pka Determination ◽  
Capillary Electrophoretic ◽  
2D Roesy ◽  
Positively Charged

In order to better understand the chiral recognition mechanisms of positively charged cyclodextrin (CD) derivatives, the synthesis, the pKa determination by 1H nuclear magnetic resonance (NMR)-pH titration and a comparative chiral capillary electrophoretic (CE) study were performed with two series of mono-substituted cationic single isomer CDs. The first series of selectors were mono-(6-N-pyrrolidine-6-deoxy)-β-CD (PYR-β-CD), mono-(6-N-piperidine-6-deoxy)-β-CD (PIP-β-CD), mono-(6-N-morpholine-6-deoxy)-β-CD (MO-β-CD) and mono-(6-N-piperazine-6-deoxy)-β-CD (PIPA-β-CD), carrying a pH-adjustable moiety at the narrower rim of the cavity, while the second set represented by their quaternarized, permanently cationic counterparts: mono-(6-N-(N-methyl-pyrrolidine)-6-deoxy)-β-CD (MePYR-β-CD), mono-(6-N-(N-methyl-piperidine)-6-deoxy)-β-CD (MePIP-β-CD), mono-(6-N-(N-methyl-morpholine)-6-deoxy)-β-CD (MeMO-β-CD) and mono-(6-N-(4,4-N,N-dimethyl-piperazine)-β-CD (diMePIPA-β-CD). Based on pH-dependent and selector concentration-dependent comparative studies of these single isomer N-heterocyclic CDs presented herein, it can be concluded that all CDs could successfully be applied as chiral selectors for the enantiodiscrimination of several negatively charged and zwitterionic model racemates. The substituent-dependent enantiomer migration order reversal of dansylated-valine using PIP-β-CD contrary to PYP-β-CD, MO-β-CD and PIPA-β-CD was also studied by 1H- and 2D ROESY NMR experiments.

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