Enhancement of chiral recognition by formation of a sandwiched complex in capillary electrophoresis.
For chiral primary amino compounds not separable by cyclodextrins alone, chiral recognition was successfully achieved by the formation of a sandwiched complex of the non-chiral 18-crown-6, the chiral amine and cyclodextrin (CD) [18-crown-6+amino compound+CD]. The separation of 1-methyl-3-phenylpropylamine and 1,2,3,4-tetrahydro-1-naphthylamine racemates showed the special function of the non-chiral 18-crown-6 on chiral recognition. By formation of the sandwiched complex, the chiral center of 1-methyl-3-phenylpropylamine was successfully recognized, and resolution of 1,2,3,4-tetrahydro-1-naphthylamine dramatically increased. In these studies, the mobility differences of the enantiomers were evaluated as a function of the concentration of cyclodextrins with and without the 18-crown-6, and as a function of the concentration of the 18-crown-6. In addition, the separations by this method were compared to those by the chiral 18-crown-6 reagent.
Huang
W X
WX
Novartis Pharmaceuticals Corp., Chemical & Analytical R & D Dept., East Hanover, NJ 07936, USA.
Xu
H
H
Fazio
S D
SD
Vivilecchia
R V
RV
D019075:Electrophoresis, Capillary / Q000379:methods*; D013237:Stereoisomerism