Interaction between 18-crown-6-tetracarboxylic acid and positional substituents of enantiomers and simultaneous separation of positional enantiomers of methyl-DL-tryptophans by capillary electrophoresis.
18-Crown-6-tetracarboxylic acid (18C6H4) is a chiral selector with high selectivity for the enantioseparation of solutes bearing the primary amine function. This work presents the simultaneous separation of positional enantiomers of methyl-DL-tryptophans by using 18C6H4 as an additive to the background electrolyte. Separation conditions such as pH, the concentration of 18C6H4, and the applied voltages have critical inference on the simultaneous separation. The addition of cyclodextrins as anionic surfactants to the background electrolyte did not improve the separation. The selector-selectand interactions between 18C6H4 and the positional enantiomers have been investigated. It was observed that both the position and type of substituents contribute to the enantioselectivity. The migration order and resolution depended on the distance from the substituents to the asymmetric carbon of the enantiomers.
Chen
Z
Z
Department of Applied Chemistry, Graduate School of Engineering, Tokyo Metropolitan University, Japan. zlchen@ecomp.metro-u.ac.jp
Uchiyama
K
K
Hobo
T
T
D043844:Crown Ethers; D003505:Cyclodextrins; D019075:Electrophoresis, Capillary / Q000379:methods*; D004988:Ethers, Cyclic; D007536:Isomerism; D008745:Methylation; D012967:Sodium Dodecyl Sulfate; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification
D043844:Crown Ethers; D003505:Cyclodextrins; D004988:Ethers, Cyclic; C090732:18-crown-6 2,3,11,12-tetracarboxylic acid; D012967:Sodium Dodecyl Sulfate; D014364:Tryptophan