Journal
ELECTROPHORESIS
Volume 29, Issue 18, Pages 3941-3948Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/elps.200800133
Keywords
Capillary electrochromatography; Chiral separation; Ligand exchange; Low molecular weight organogels; Supramolecular
Funding
- BMBF-Germany-MOS
- Israel Water Technology Program
- Ring Foundation
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Chiral electroseparation is demonstrated, for the first time, by a low molecular weight organogel filled capillary. Five pairs of dansylated amino acids were separated by copper ligand exchange on a trans- (1S,2S)-1,2-bis-(dodecylamido) cyclohexane (1) gel in methanol. Low molecular weight organogels are emerging materials that form stable, fibrillar, thermoreversible and thixotropic gels without covalent bonding of their monomeric building blocks. The dependence of chiral resolution and complex formation stability on the pH*, the. ratio between copper and the D-valine selector, as well as other parameters were investigated revealing trends that were unparalleled in previously reports on copper ligand exchange of dansylated amino acids. These observations were explained in view of a simple stacking model of (1) and the difference in axial ligation of the amide carbonyl backbone of the gel to the dansyl D- or L-amino acid: D-valine:copper ternary complexes.
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