Visual chiral recognition of aromatic amino acids with (S)-mandelic acid-based ionic liquids via complexation

Ma, Xiaofei; Du, Yingxiang; Zhu, Xin‐Qi; Yang, Jiangxia

doi:10.1016/j.talanta.2020.121083

Cited by 18 publications

(10 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore, only several examples are reported for chiral recognition based on ionic selectors by using UV-spectroscopy and circular dichroism spectroscopy [142][143][144][145][146]. It is interesting to find that, a (S)-phenylalaninebased ionic molecule can be used as the visual detector for tryptophan (Figure 4) [142].…”

Section: Spectral Analysismentioning

confidence: 99%

Recent advances of the ionic chiral selectors for chiral resolution by chromatography, spectroscopy and electrochemistry

Fan

et al. 2021

J of Separation Science

View full text Add to dashboard Cite

Ionic chiral selectors have been received much attention in the field of asymmetric catalysis, chiral recognition, and preparative separation. It has been shown that the addition of ionic chiral selectors can enhance the recognition efficiency dramatically due to the presence of multiple intermolecular interactions, including hydrogen bond, π-π interaction, van der Waals force, electrostatic ion-pairing interaction, and ionic-hydrogen bond. In the initial research stage of the ionic chiral selectors, most of work center on the application in chromatographic separation (capillary electrophoresis, high-performance liquid chromatography, and gas chromatography). Differently, more and more attention has been paid on the spectroscopy (nuclear magnetic resonance, fluorescence, ultraviolet and visible absorption spectrum, and circular dichroism spectrum) and electrochemistry in recent years. In this tutorial review as regards the ionic chiral selectors, we discuss in detail the structural features, properties, and their application in chromatography, spectroscopy, and electrochemistry.

show abstract

Section: Spectral Analysismentioning

confidence: 99%

Recent advances of the ionic chiral selectors for chiral resolution by chromatography, spectroscopy and electrochemistry

Fan

et al. 2021

J of Separation Science

View full text Add to dashboard Cite

show abstract

“…The authors studied additionally different factors such as the alkyl chain length of cations of ionic liquids, the amount of copper acetate, the molar ratio of ILs/Cu 2+ , the amount of water and racemic phenylalanine, the resolution time and the resolution temperature, providing the best efficiency of enantioseparation. Ma et al [164] proposed two functionalized chiral ionic liquids derived from (S)-mandelic acid (1-butyl-3-methylimidazolium mandelate and N-butyl-N-methylpyrrolidinium mandelate) beneficial for visual chiral recognition of phenylalanine, tryptophan, tyrosine and phenylglycine. In the presence of Cu(II), the resolution of racemic tryptophan achieved enantiomeric excess values (94.2% for the first CIL and 95.1% for the second one in solid phase).…”

Section: The Solid-liquid Two-phase System With Cilsmentioning

confidence: 99%

“…Other racemates: (R/S)-tryptosol, (R/S)-2-phenylglycinol, and the remaining 18 amino acids were also successfully separated with the yields ranges from 90% to 94% using the same method. Ma et al [164] proposed two functionalized chiral ionic liquids derived from (S)-mandelic acid (1-butyl-3-methylimidazolium mandelate and N-butyl-N-methylpyrrolidinium mandelate) beneficial for visual chiral recognition of phenylalanine, tryptophan, tyrosine and phenylglycine. In the presence of Cu(II), the resolution of racemic tryptophan achieved enantiomeric excess values (94.2% for the first CIL and 95.1% for the second one in solid phase).…”

Section: The Solid-liquid Two-phase System With Cilsmentioning

confidence: 99%

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Flieger

Feder‐Kubis

Tatarczak-Michalewska

2020

IJMS

View full text Add to dashboard Cite

Ionic liquids (ILs) are chemical compounds composed of ions with melting points below 100 °C exhibiting a design feature. ILs are commonly used as the so-called green solvents, reagents or highly efficient catalysts in varied chemical processes. The huge application potential of ionic liquids (IL) justifies the growing interest in these compounds. In the last decade, increasing attention has been devoted to the development of new methods in the synthesis of stable chiral ionic liquids (CILs) and their application in various separation techniques. The beginnings of the successful use of CILs to separate enantiomers date back to the 1990 s. Most chiral ILs are based on chiral cations or chiral anions. There is also a limited number of CILs possessing both a chiral cation and a chiral anion. Due to the high molecular diversity of both ions, of which at least one has a chiral center, we have the possibility to design a large variety of optically active structures, thus expanding the range of CIL applications. Research utilizing chiral ionic liquids only recently has become more popular. However, it is the area that still has great potential for future development. This review aimed to describe the diversity of structures, properties and examples of applications of chiral ionic liquids as new chiral solid materials and chiral components of the anisotropic environment, providing chiral recognition of enantiomeric analytes, which is useful in liquid chromatography, countercurrent chromatography and other various CIL-based extraction techniques including aqueous biphasic (ABS) extraction systems, solid–liquid two-phase systems, liquid–liquid extraction systems with hydrophilic CILs, liquid–liquid extraction systems with hydrophobic CILs, solid-phase extraction and induced-precipitation techniques developed in the recent years. The growing demand for pure enantiomers in the pharmaceutical and food industries sparks further development in the field of extraction and separation systems modified with CILs highlighting them as affordable and environmentally friendly both chiral selectors and solvents.

show abstract

“…Possessing both the ingredients of ILs and chirality, chiral ILs (CILs) have drawn considerable attention more recently. Many reports have demonstrated that CILs have certain chiral recognition abilities in enantioseparation [22][23][24][25], visual chiral discrimination [26,27], and asymmetric synthesis [28,29]. Whereas, most CILs which were used for enantioseparation in CE is derived from amino acids and their derivatives [30,31].…”

Section: Introductionmentioning

confidence: 99%

Investigation on improvement of enantioseparation in capillary electrophoresis based on maltodextrin by chiral ionic liquids

Chen

Cai

2022

J of Separation Science

Self Cite

View full text Add to dashboard Cite

Taking advantage of chiral ionic liquids, this study deals with the improvement of the enantioseparation performance of a traditional chiral selector (maltodextrin) in capillary electrophoresis. Herein, two polyhydroxy compoundbased chiral ionic liquids, namely tetramethylammonium-D-gluconic acid and tetramethylammonium-shikimic acid were designed and utilized as additives for chiral separation for the first time. The synergistic systems provided much better enantioseparations of twelve model drugs compared to the single maltodextrin system. These model analytes contained analgesics, antidepressants, antiallergic drugs, antifungal drugs, antihypertensive drugs, and antiparkinsonian drugs. After optimizing the separation conditions, the chiral recognition mechanism was probed by means of ultraviolet spectroscopy, nuclear magnetic resonance, and molecular modeling. The results of spectroscopic and computational analyses were in good consistency with enantioseparation outcomes. Finally, the proposed method was successfully used for the determination of the enantiomeric purity of duloxetine hydrochloride.

show abstract

Visual chiral recognition of aromatic amino acids with (S)-mandelic acid-based ionic liquids via complexation

Cited by 18 publications

References 30 publications

Recent advances of the ionic chiral selectors for chiral resolution by chromatography, spectroscopy and electrochemistry

Recent advances of the ionic chiral selectors for chiral resolution by chromatography, spectroscopy and electrochemistry

Chiral Ionic Liquids: Structural Diversity, Properties and Applications in Selected Separation Techniques

Investigation on improvement of enantioseparation in capillary electrophoresis based on maltodextrin by chiral ionic liquids

Contact Info

Product

Resources

About