Fast enantioseparation of arylglycine amides by capillary electrophoresis with highly sulfated-beta-cyclodextrin as a chiral selector.
Nine racemic arylglycine amides were synthesized and successfully enantioseparated by capillary electrophoresis (CE) using highly sulfated beta-cyclodextrin (HS-beta-CD) as a chiral selector. Baseline enantioseparation of the analytes was obtained around neutral pH but not in the acidic conditions that are commonly used. HS-beta-CD content, buffer pH, type and concentration, and organic modifier concentration were studied and optimized for fast and efficient separation. A chiral CE separation system composed of 1.5% (w/v) HS-beta-CD, 0 to 10% (v/v) methanol and 20 mM 3-(N-morpholino)propanesulfonic acid at pH 6.5 was shown suitable for baseline enantioseparation of the mentioned amides within 6 min, including simultaneous enantioseparation of three positional isomer series (methyl-, methoxyl or chloro-substituted). By using this system, D-enantiomers migrated ahead of the L-enantiomers and the enantiomeric resolution order of arylglycine amides was more or less parallel to the pK(a), order of the analytes.
Guo
Lei
L
Laboratory of Chemical Biology, Center for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, P.O. Box 2709, Beijing 100080, People's Republic of China.
Lin
Shuang J
SJ
Yang
Yi F
YF
Qi
Li
L
Wang
Mei X
MX
Chen
Yi
Y
D000577:Amides / Q000032:analysis*; D002021:Buffers; D003505:Cyclodextrins / Q000737:chemistry*; D019075:Electrophoresis, Capillary / Q000379:methods*; D005998:Glycine / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D013237:Stereoisomerism; D047392:beta-Cyclodextrins
D000577:Amides; D002021:Buffers; D003505:Cyclodextrins; D047392:beta-Cyclodextrins; C031215:betadex; D005998:Glycine