Chiral separation of dansyl amino acids in capillary electrophoresis using mono-(3-methyl-imidazolium)-beta-cyclodextrin chloride as selector.
Enantioseparations of fourteen dansyl amino acids were achieved by using a positively-charged single-isomer beta-cyclodextrin, mono-(3-methyl-imidazolium)-beta-cyclodextrin chloride, as a chiral selector. Separation parameters such as buffer pH, selector concentration, separation temperature, and organic modifier were investigated for the enantioseparation in order to achieve the maximum possible resolution. Chiral separation of dansyl amino acids was found to be highly dependent on pH since the degree of protonation of these amino acids can alter the strength of electrostatic interaction and/or inclusion complexation between each enantiomer and chiral selector. In general, the chiral resolution of dansyl amino acids was enhanced at higher pH, which indicates that the carboxylate group on the analytes may interact with the imidazolium group of cationic cyclodextrin. For most analytes, a distinct maximum in enantioresolution was obtained at pH 8.0. Moreover, the chiral separation can be further improved by careful tuning of the separation parameters such as higher selector concentration (e.g. 10 mM), lower temperature, and addition of methanol. Enantioseparation of a standard mixture of these dansyl amino acids was further achieved in a single run within 30 min.
Tang
Weihua
W
Department of Chemistry, National University of Singapore, Singapore.
Ong
Teng Teng
TT
Ng
Siu-Choon
SC
D000596:Amino Acids / Q000302:isolation & purification*; D002021:Buffers; D002712:Chlorides / Q000737:chemistry*; D003619:Dansyl Compounds / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013696:Temperature; D047392:beta-Cyclodextrins / Q000737:chemistry*
C496308:1-benzyl-3-methylimidazolium; D000596:Amino Acids; D002021:Buffers; D002712:Chlorides; D003619:Dansyl Compounds; D007093:Imidazoles; D047392:beta-Cyclodextrins; C031215:betadex