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Influence of (hydroxy)alkylamino substituents on enantioseparation ability of single‐isomer amino‐β‐cyclodextrin derivatives in chiral capillary electrophoresis
Author(s) -
Iványi Róbert,
Jicsinszky László,
Juvancz Zoltán,
Roos Natascha,
Otta Klára,
Szejtli József
Publication year - 2004
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/elps.200406030
Subject(s) - enantiomer , chemistry , steric effects , capillary electrophoresis , cyclodextrin , amino acid , selectivity , stereoisomerism , mandelic acid , hydrogen bond , stereochemistry , stereoselectivity , beta cyclodextrins , resolution (logic) , chromatography , medicinal chemistry , organic chemistry , molecule , catalysis , biochemistry , artificial intelligence , computer science
A family of single‐isomer amino‐β‐cyclodextrin (amino‐β‐CD) derivatives containing an amino or (hydroxy)alkylamino group in one of the primary positions has been synthesized. The steric effect and hydrogen bond forming ability of the different substituents on enantioseparation of acidic enantiomers has been studied by capillary electrophoresis (CE). Three enantiomeric model compounds (mandelic acid, cis ‐permethrinic acid, and cis ‐deltamethrinic acid) having significantly different apparent complex stability constants with β‐CD were applied in the experiments. Dependence of separation selectivity, resolution as well as mobility difference on chiral selector concentration (0.1–20 m M , pH 6.0) was investigated. Each amino‐β‐CD showed higher enantioselectivity than the native β‐CD. One hydroxyalkyl group attached to the primary amino N ‐atom significantly increased both the enantioselectivity and the resolution compared to the primary amino‐β‐CD, while two hydroxyalkyl moieties decreased them due to the predominance of steric hindrance. The value of the apparent complex stability constants obtained suited well the mobility difference model (by Wren). On the other hand, the optimum selector concentrations calculated according to the model were slightly lower than the experienced concentrations giving the maximum enantioresolution of enantiomers.