TY - JOUR
T1 - Chiral separation of local anaesthetics with capillary electrophoresis. Evaluation of the inclusion complex of the enantiomers with heptakis(2,6-di-O-methyl)-β-cyclodextrin
AU - Sänger-van De Griend, C. E.
AU - Gröningsson, K.
AU - Westerlund, Douglas
PY - 1996
Y1 - 1996
N2 - A chiral capillary electrophoresis system for the high-resolution separation of the enantiomers of the local anaesthetics mepivacaine, ropivacaine, bupivacaine and prilocaine is described. Triethanolamine was added to the background electrolyte to obtain a negative electroosmotic flow and hence higher resolutions. The interactions of the local anaesthetics and their chemical analogues with the chiral selector, dimethyl-β-cyclodextrin, were studied. From a model describing chiral capillary electrophoresis, the association equilibrium constants were determined by curve-fitting. The separation of mepivacaine, ropivacaine and bupivacaine was due to the different mobilities of the free analytes in solution, whereas the separation of a pair of enantiomers of a single analyte was due to differences between the association equilibrium constants K1 and K2. Branching of the alkyl chain, which was situated close to the cavity in the inclusion complex, had strong effects on the chiral separation of the enantiomers.
AB - A chiral capillary electrophoresis system for the high-resolution separation of the enantiomers of the local anaesthetics mepivacaine, ropivacaine, bupivacaine and prilocaine is described. Triethanolamine was added to the background electrolyte to obtain a negative electroosmotic flow and hence higher resolutions. The interactions of the local anaesthetics and their chemical analogues with the chiral selector, dimethyl-β-cyclodextrin, were studied. From a model describing chiral capillary electrophoresis, the association equilibrium constants were determined by curve-fitting. The separation of mepivacaine, ropivacaine and bupivacaine was due to the different mobilities of the free analytes in solution, whereas the separation of a pair of enantiomers of a single analyte was due to differences between the association equilibrium constants K1 and K2. Branching of the alkyl chain, which was situated close to the cavity in the inclusion complex, had strong effects on the chiral separation of the enantiomers.
KW - Capillary electrophoresis
KW - Dimethyl-β-cyclodextrin
KW - Enantiomer separation
KW - Local anaesthetics
KW - Triethanolamine
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U2 - 10.1007/BF02290307
DO - 10.1007/BF02290307
M3 - Article
AN - SCOPUS:0029863123
SN - 0009-5893
VL - 42
SP - 263
EP - 268
JO - Chromatographia
JF - Chromatographia
IS - 5-6
ER -