Separation and on-line distinction of enantiomers: a non-aqueous capillary electrophoresis Fourier transform infrared spectroscopy study.
We report on the separation and on-line distinction of (R,S)-3,5-dinitrobenzoyl leucine (DNB-Leu) enantiomers with non-aqueous capillary electrophoresis (CE) and Fourier transform infrared (FT-IR) spectroscopic detection using O-(tert-butyl carbamoyl) quinine (tBuCQN) as the chiral selector (CS). Due to stereoselective intermolecular interactions--particularly ionic interactions, hydrogen bonding, and pi-pi-interactions--the enantiomers undergo enantioselective complex and ion-pair formation, respectively, with the CS enabling CE separation and direct identification with FT-IR detection. Especially the (S)-enantiomer of the analyte shows significant changes in the mid-infrared region upon complexation, allowing for a clear spectral distinction between both enantiomers. In this way FT-IR spectroscopy represents a novel and attractive detection method for CE enantiomeric separations providing qualitative stereochemical information on the interactions between the chiral selector and the enantiomers, which is hardly accessible by other CE detection methods.
Hinsmann
Peter
P
Institute of Chemical Technologies and Analytics, Vienna University of Technology, Getreidemarkt 9/164, A-1060 Vienna, Austria.
Arce
Lourdes
L
Svasek
Peter
P
Lämmerhofer
Michael
M
Lendl
Bernhard
B
D004136:Dinitrobenzenes / Q000032:analysis / Q000737:chemistry; D019075:Electrophoresis, Capillary / Q000379:methods*; D007930:Leucine / Q000031:analogs & derivatives* / Q000032:analysis / Q000737:chemistry; D009862:Online Systems; D017550:Spectroscopy, Fourier Transform Infrared / Q000379:methods*; D013237:Stereoisomerism
D004136:Dinitrobenzenes; C465293:dinitrobenzoyl leucine; D007930:Leucine