Investigation of the synergistic effect with amino acid-derived chiral ionic liquids as additives for enantiomeric separation in capillary electrophoresis

Zhang, Jinjing; Du, Yingxiang; Zhang, Qi; Chen, Jiaquan; Xu, Gelin; Tao, Yu; Hua, Xiaoyi

doi:10.1016/j.chroma.2013.09.064

Cited by 68 publications

(32 citation statements)

References 32 publications

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“…As mentioned earlier, the chiral separation performance of the synergistic system was evaluated by varying different electrophoretic conditions. One of them was the AAIL concentration, which was expected, based on previous reports , to have a significant effect on enantiorecognition.…”

Section: Resultsmentioning

confidence: 89%

“…The potential use of AAILs as additives has been widely reported, over the years, in CE applications [, , ]. As mentioned earlier, the chiral separation performance of the synergistic system was evaluated by varying different electrophoretic conditions.…”

Section: Resultsmentioning

confidence: 99%

“…applied a glycogen‐based synergistic system with two chiral ILs as additives in CE in order to evaluate their potential enantioselectivity . The same group also investigated the combination of methyl‐β‐CD, hydroxypropyl‐β‐CD or glucose‐β‐CD with different chiral ILs in CE enantioseparations . In their study, the synergistic effect proved to be significant for half of the analytes examined, and particularly for pranoprofen, naproxen, and warfarin.…”

Section: Introductionmentioning

confidence: 99%

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Combined use of l‐alanine tert butyl ester lactate and trimethyl‐β‐cyclodextrin for the enantiomeric separations of 2‐arylpropionic acids nonsteroidal anti‐inflammatory drugs

Mavroudi

Kapnissi‐Christodoulou

2015

Electrophoresis

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In this study, a new CE method, employing a binary system of trimethyl-β-CD (TM-β-CD) and a chiral amino acid ester-based ionic liquid (AAIL), was developed for the chiral separation of seven 2-arylpropionic acid nonsteroidal anti-inflammatory drugs (NSAIDs). In particular, the enantioseparation of ibuprofen, ketoprofen, carprofen, indoprofen, flurbiprofen, naproxen, and fenoprofen was improved significantly by supporting the BGE with the chiral AAIL l-alanine tert butyl ester lactate (l-AlaC4 Lac). Parameters, such as concentrations of TM-β-CD and l-AlaC4 Lac, and buffer pH, were systematically examined in order to optimize the chiral separation of each NSAID. It was observed that the addition of the AAIL into the BGE improved both resolution and efficiency significantly. After optimization of separation conditions, baseline separation (Rs >1.5) of five of the analytes was achieved in less than 11 min, while the resolution of ibuprofen and flurbiprofen was approximately 1.2. The optimized enantioseparation conditions for all analytes involve a BGE of 5 mM sodium acetate/acetic acid (pH 5.0), an applied voltage of 30 kV, and a temperature of 20°C. In addition, the results obtained by computing the %-RSD values of the EOF and the two enantiomer peaks, demonstrated excellent run-to-run, batch-to-batch, and day-to-day reproducibilities.

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Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Combined use of l‐alanine tert butyl ester lactate and trimethyl‐β‐cyclodextrin for the enantiomeric separations of 2‐arylpropionic acids nonsteroidal anti‐inflammatory drugs

Mavroudi

Kapnissi‐Christodoulou

2015

Electrophoresis

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“…The designable properties of chiral ILs open a way of developing new chiral recognition material for enantiomeric separation. However, only a few papers have reported the application of chiral ILs in CE for enantioseparation , and the use of chiral ILs as the sole chiral selector in an electrophoretic or a chromatographic system was reported in only three papers .…”

Section: Introductionmentioning

confidence: 99%

Tetramethylammonium‐lactobionate: A novel ionic liquid chiral selector based on saccharides in capillary electrophoresis

Zhang

et al. 2015

Electrophoresis

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Chiral ionic liquids (ILs) have aroused widespread interest in separation science; however, only a few papers have reported the application of chiral ILs in CE for enantioseparation, and the use of chiral ILs as the sole chiral selector in an electrophoretic or a chromatographic system was reported in only three papers. In this study, we designed a lactobionic acid LA-based IL, tetramethylammonium-lactobionate (TMA-LA), and it is very interesting to find that the chiral separation capability can be remarkably improved when a conventional saccharide chiral selector evolved into an IL chiral selector. A comparative study of the enantiorecognition capability of three separation systems (single LA system, LA + TMA-chloride (TMA-Cl) system, and TMA-LA IL system) was also conducted, and the results showed that the use of TMA-LA IL as the sole chiral selector exhibited a remarkable superiority. A series of parameters affecting the enantioseparation, such as the type and proportion of organic modifier, buffer composition and pH, chiral selector concentration, as well as applied voltage were systematically investigated. The best enantioseparation was obtained at pH 7.6 using a 40 mM borax buffer with 40% v/v methanol, 200 mM TMA-LA, and 20 kV applied voltage. It is the first time that a saccharide-based IL is evaluated as a sole chiral selector in CE, and we hope this study would provide a new direction for the development of novel ILs chiral selectors based on conventional chiral selectors.

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“…[18][19][20][21] One important feature of ILs is that we can vary the cation or anion to change their physical and chemical properties to meet practical needs. [24][25][26][27][28][29] Amino acid ionic liquids (AAILs) were synthesized from natural amino acids; thus, most AAILs have stereogenic centers. They have gained widespread interest in separation science.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Enantioselectivity of Tetramethylammonium L‐hydroxyproline Ionic Liquid as a Novel Chiral Ligand in Ligand‐Exchange CE and Ligand‐Exchange MEKC

Liu

Chen

et al. 2014

Chirality

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Chiral ionic liquids (ILs) have drawn more and more attention in separation science; however, only a few papers focused on the application of chiral ILs as chiral ligands in LE-CE. In this article, a novel amino acid ionic liquid (AAIL), tetramethylammonium L-hydroxyproline ([TMA][L-OH-Pro]), was first applied as a chiral ligand to evaluate its enantioselectivity towards several aromatic amino acids in ligand-exchange capillary electrophoresis (LE-CE) and ligand-exchange micellar electrokinetic capillary chromatography (LE-MEKC). In the LE-CE system, excellent separations were achieved for tryptophan (Rs = 3.03) and 3, 4-dihydroxyphenylalanine (DOPA) (Rs = 4.35). Several parameters affecting the enantioseparation were systematically investigated, including AAIL concentration, type and concentration of central metal ion, buffer pH, as well as applied voltage. The optimum separation was obtained with 60 mM AAIL containing 30 mM Cu (II) at pH 4.5. Additionally, an LE-MEKC system was established to further study the enantioselectivity of [TMA][L-OH-Pro] towards selected analytes. As observed, the separations of the enantiomers of tryptophan, phenylalanine, and histidine were all improved compared to the LE-CE system. The results indicated that the application of AAILs as chiral ligands is a promising method in chiral separation science.

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Investigation of the synergistic effect with amino acid-derived chiral ionic liquids as additives for enantiomeric separation in capillary electrophoresis

Cited by 68 publications

References 32 publications

Combined use of l‐alanine tert butyl ester lactate and trimethyl‐β‐cyclodextrin for the enantiomeric separations of 2‐arylpropionic acids nonsteroidal anti‐inflammatory drugs

Combined use of l‐alanine tert butyl ester lactate and trimethyl‐β‐cyclodextrin for the enantiomeric separations of 2‐arylpropionic acids nonsteroidal anti‐inflammatory drugs

Tetramethylammonium‐lactobionate: A novel ionic liquid chiral selector based on saccharides in capillary electrophoresis

Investigation of the Enantioselectivity of Tetramethylammonium L‐hydroxyproline Ionic Liquid as a Novel Chiral Ligand in Ligand‐Exchange CE and Ligand‐Exchange MEKC

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