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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
Author(s) -
Chen Zilin,
Uchiyama Katsumi,
Hobo Toshiyuki
Publication year - 2001
Publication title -
electrophoresis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.666
H-Index - 158
eISSN - 1522-2683
pISSN - 0173-0835
DOI - 10.1002/1522-2683(20017)22:11<2136::aid-elps2136>3.0.co;2-z
Subject(s) - enantiomer , chemistry , electrolyte , structural isomer , capillary electrophoresis , amine gas treating , selectivity , resolution (logic) , chromatography , stereochemistry , organic chemistry , electrode , artificial intelligence , computer science , catalysis
18‐Crown‐6‐tetracarboxylic acid (18C6H 4 ) 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 18C6H 4 as an additive to the background electrolyte. Separation conditions such as pH, the concentration of 18C6H 4 , 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 18C6H 4 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.