Development of stereoselective nonaqueous capillary electrophoresis system for the resolution of cationic and amphoteric analytes.
A stereoselective ion-pair nonaqueous capillary electrophoresis (NACE) method employing the partial filling technique with N-derivatized amino acids, e.g., (R)- and (S)-3,5-dinitrobenzoyl-leucine (DNB-Leu), as chiral selector for the separation of "pseudoenantiomeric" cinchona alkaloid derivatives and other structurally related basic compounds like the enantiomers of mefloquine is presented. Originating from NACE with cinchona alkaloid derivatives as chiral counterions, this method was developed by application of the reciprocity principle of chiral recognition, which was proven to be valid for stereoselective ion-pair capillary electrophoresis (CE). A variety of basic and amphoteric selectands (SAs) could be well resolved. Thereby, the separation was primarily based on stereoselective ion-pair formation of corresponding SA stereoisomers and mobility differences of free and complexed (ion-paired) SAs. Additionally, in the case of diastereomeric SAs, naturally existing mobility differences between the diastereomers played also a role, but was shown by control experiments with racemic DNB-Leu and without selector (SO) to be of minor contribution to overall separation selectivity. Due to its simplicity, speed, and good reproducibility, the established method can be utilized for fast screening of cationic as well as amphoteric chiral compounds, and therefore is a valuable tool in the development of new chiral selectors and chiral stationary phases. Small sample amounts of the SO (4-5 mg) and only analytical amounts of SAs are needed, and about 20-50 compounds per day can be tested.
Zarbl
E
E
Institute of Analytical Chemistry, University of Vienna, Austria.
Lämmerhofer
M
M
Franco
P
P
Petracs
M
M
Lindner
W
W
D002219:Carbamates / Q000737:chemistry / Q000302:isolation & purification; D002412:Cations; D019075:Electrophoresis, Capillary / Q000379:methods*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007930:Leucine / Q000031:analogs & derivatives* / Q000737:chemistry; D015767:Mefloquine / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D009579:Nitrobenzoates / Q000737:chemistry; D011802:Quinidine / Q000737:chemistry / Q000302:isolation & purification; D011803:Quinine / Q000737:chemistry / Q000302:isolation & purification; D013237:Stereoisomerism
D002219:Carbamates; D002412:Cations; D007202:Indicators and Reagents; D009579:Nitrobenzoates; C051872:N-(3,5-dinitrobenzoyl)leucine; D011803:Quinine; D007930:Leucine; D011802:Quinidine; D015767:Mefloquine