Citation: HUANG Lu, YU Lishuang, CHEN Yiting. Application of 1-ethyl-3-methyl imidazole L-lactate as the chiral ligand for the enantioseparation of amino acids[J]. Chinese Journal of Chromatography, ;2014, 32(11): 1225-1229. doi: 10.3724/SP.J.1123.2014.06040 shu

Application of 1-ethyl-3-methyl imidazole L-lactate as the chiral ligand for the enantioseparation of amino acids

1.
1. Department of Chemistry and Chemical Engineering, Minjiang University, Fuzhou 350108, China;

Received Date: 28 June 2014
Available Online: 22 August 2014
Fund Project: 国家自然科学基金项目(81202913) (81202913)福建省中青年教师教育科研项目(JA14248). (JA14248)

Enantioseparation of tryptophan enantiomers (Trys), tyrosine enantiomers (Tyrs) and phenylamine enantiomers (Phes) by chiral ligand exchange capillary electrophoresis (CLE-CE) using 1-ethyl-3-methyl imidazole L-lactate ([EMIM][L-Lac]) as the chiral ligand was studied. The effects of background electrolytes and central ions, the molar ratio and concentration of the chiral ligand and central ion, running buffer solution pH on the enantioseparation of Trys, Phes and Tyrs were investigated. Good enantioseparation of three pairs of enantiomers were obtained with 40.0 mmol/L [EMIM][L-Lac] and 20.0 mmol/L cupric chloride (pH 4.5). To validate the good behavior of [EMIM][L-Lac], L-lactate (L-Lac) was further used as the chiral ligand for the enantioseparation of Trys. The contrast experiment showed that Trys could only be partially enantioseparated by L-Lac. Moreover, the enantioseparation was improved by adding 1-ethyl-3-methyl imidazole acetate (EMIM-Ace) which markedly prolonged the migration time of Trys to more than 30 min. In contrast, the migration time of Trys was obtained in 15 min by [EMIM][L-Lac]. Finally, the enantioseparation mechanism was further discussed. The experimental results showed that in the EMIM-Ace assisting L-Lac system, EMIM-Ace was only used to suppress the electroosmotic flow and was not involved in the chiral ligand exchange reaction, while in the [EMIM][L-Lac] system, the chiral ligand taking part in the reaction was mainly unionized [EMIM][L-Lac] rather than L-Lac formed by ionized L-Lac ions.
- chiral ionic liquid,
- 1-ethyl-3-methyl imidazole L-lactate,
- chiral ligand exchange capillary electrophoresis,
- chiral separation
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