| Amino acid ionic liquids as chiral ligands in ligand-exchange chiral separations. | |
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MedLine Citation:
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PMID: 19691066 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Recently, amino acid ionic liquids (AAILs) have attracted much research interest. In this paper, we present the first application of AAILs in chiral separation based on the chiral ligand exchange principle. By using 1-alkyl-3-methylimidazolium L-proline (L-Pro) as a chiral ligand coordinated with copper(II), four pairs of underivatized amino acid enantiomers-dl-phenylalanine (dl-Phe), dl-histidine (dl-His), dl-tryptophane (dl-Trp), and dl-tyrosine (dl-Tyr)-were successfully separated in two major chiral separation techniques, HPLC and capillary electrophoresis (CE), with higher enantioselectivity than conventionally used amino acid ligands (resolution (R(s))=3.26-10.81 for HPLC; R(s)=1.34-4.27 for CE). Interestingly, increasing the alkyl chain length of the AAIL cation remarkably enhanced the enantioselectivity. It was inferred that the alkylmethylimidazolium cations and L-Pro form ion pairs on the surface of the stationary phase or on the inner surface of the capillary. The ternary copper complexes with L-Pro are consequently attached to the support surface, thus inducing an ion-exchange type of retention for the dl-enantiomers. Therefore, the AAIL cation plays an essential role in the separation. This work demonstrates that AAILs are good alternatives to conventional amino acid ligands for ligand-exchange-based chiral separation. It also reveals the tremendous application potential of this new type of task-specific ILs. |
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Authors:
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Qian Liu; Kangkang Wu; Fei Tang; Lihua Yao; Fei Yang; Zhou Nie; Shouzhuo Yao |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Chemistry (Weinheim an der Bergstrasse, Germany) Volume: 15 ISSN: 1521-3765 ISO Abbreviation: Chemistry Publication Date: 2009 Sep |
Date Detail:
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Created Date: 2009-09-28 Completed Date: 2010-01-19 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9513783 Medline TA: Chemistry Country: Germany |
Other Details:
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Languages: eng Pagination: 9889-96 Citation Subset: IM |
Affiliation:
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State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, China. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemistry*,
isolation & purification Chromatography, Micellar Electrokinetic Capillary Copper / chemistry Electrophoresis, Capillary Imidazoles / chemistry Ionic Liquids / chemistry* Ligands* Proline / chemistry Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Imidazoles; 0/Ionic Liquids; 0/Ligands; 147-85-3/Proline; 7440-50-8/Copper |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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