Functional amino acid ionic liquids as solvent and selector in chiral extraction

Tang, Fei; Zhang, Qianli; Ren, Dandan; Nie, Zhou; Liu, Qian; Yao, Shouzhuo

doi:10.1016/j.chroma.2010.05.013

Cited by 95 publications

(70 citation statements)

References 54 publications

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“…Tang and coauthors 211 employed functional amino-acid-based ILs (AAILs) as solvents and selectors for the LLE of racemic mixtures of amino acids. With these ILs as an acceptor phase and ethyl acetate as a donor phase, it was possible to extract the l -enantiomer into the IL phase with higher efficiencies.…”

Section: Amino Acidsmentioning

confidence: 99%

Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends

et al. 2017

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Ionic liquids (ILs) have been proposed as promising media for the extraction and separation of bioactive compounds from the most diverse origins. This critical review offers a compilation on the main results achieved by the use of ionic-liquid-based processes in the extraction and separation/purification of a large range of bioactive compounds (including small organic extractable compounds from biomass, lipids, and other hydrophobic compounds, proteins, amino acids, nucleic acids, and pharmaceuticals). ILs have been studied as solvents, cosolvents, cosurfactants, electrolytes, and adjuvants, as well as used in the creation of IL-supported materials for separation purposes. The IL-based processes hitherto reported, such as IL-based solid–liquid extractions, IL-based liquid–liquid extractions, IL-modified materials, and IL-based crystallization approaches, are here reviewed and compared in terms of extraction and separation performance. The key accomplishments and future challenges to the field are discussed, with particular emphasis on the major lacunas found within the IL community dedicated to separation processes and by suggesting some steps to overcome the current limitations.

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Section: Amino Acidsmentioning

confidence: 99%

Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends

et al. 2017

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“…With the addition of L-leucine, L-proline, L-phe, or N,N-dimethyl-L-phenylalanine, many enantiomers and derivatized amino acids, such as tryptophan, phenylalanine, warfarin, and valine, have been successfully resolutioned [15][16][17][18]. Considering that DMMD was an analogue of amine acid, the diastereomeric mixed-ligand complexes containing amino acide, bivalence copper, and DMMD could be formed by their carboxylic group and neighboring amino group, which resulted in the cis-and trans-configurations.…”

Section: Resultsmentioning

confidence: 99%

Chiral ligand-exchange high-performance liquid chromatography with copper (II)-L-phenylalanine complexes for separation of 3,4-dimethoxy-α-methylphenylalanine racemes

Jia

Xue

et al. 2014

Anal Bioanal Chem

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L-3, 4-dimethoxy-α-methylphenylalanine (L-DMMD) is an important intermediate for the synthesis of 3-hydroxy-α-methyl-L-tyrosine (L-methyldopa). This paper describes an efficient, accurate, and low-priced method of high-performance liquid chromatography (HPLC) using chiral mobile phase and conventional C18 column to separate L-DMMD from its enantiomers. The effects of ligands, copper salts, organic modifiers, pHs of mobile phase, and temperatures on the retention factors (k') and selectivity (α) were evaluated to achieve optimal separation performance. Then, thermal analysis of the optimal separation conditions was investigated as well. It was confirmed that the optimal mobile phase was composed of 20 % (v/v) methanol, 8 mM L-phenylalanine (L-Phe), and 4 mM cupric sulfate in water of pH 3.2, and the column temperature was set at 20 °C. Baseline separation of two enantiomers could be obtained through the conventional C18 column with a resolution (R) of 3.18 in less than 18 min. Thermodynamic data (∆∆H and ∆∆S) obtained by Van't Hoff plots revealed the chiral separation was an enthalpy-controlled process. To the best of our knowledge, this is the first report regarding the enantioseparation of DMMD by chiral ligand-exchange HPLC.

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“…Excellent extraction efficiency was also obtained by using this technology in the extraction of active ingredients from natural plants (Tan et al, 2012a(Tan et al, , 2012b. There have been several reports on the applications of chiral ionic liquids (Tang et al, 2010) and hydrophobic ionic liquids (Yue et al, 2014) in the chiral separation of liquid-liquid systems. However, there have been few reports on the chiral separation of enantiomers using hydrophilic ionic liquid/salt-based ATPS.…”

Section: Methodsmentioning

confidence: 91%

Chiral separation of α-cyclohexylmandelic acid enantiomers using ionic liquid/salt aqueous two-phase system

Chen

Tan

2015

Chemical Papers

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In this paper, an ionic liquid-based aqueous two-phase system (ILATPS) was applied to the chiral separation of α-cyclohexylmandelic acid (α-CHMA) enantiomers with hydroxypropyl-β-cyclodextrin (HP-β-CD) as the chiral selector. Several influencing parameters were investigated including the types and concentration of ionic liquids, the amount of phase-forming salt, temperature, mixing time, pH, and the content of HP-β-CD. The results showed that not all ILATPS had the ability to chirally recognise the selected enantiomers and that [C4mim]BF4/(NH4)2SO4-based ATPS possessed the best enantioseparation ability of the investigated ILATPSs. Under optimal conditions, the separation factor (α) attained 1.59 in a single-step extraction. ILATPS is much "greener" than other liquid-liquid extraction systems, showing its potential for application to the chiral separation.

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Functional amino acid ionic liquids as solvent and selector in chiral extraction

Cited by 95 publications

References 54 publications

Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends

Ionic-Liquid-Mediated Extraction and Separation Processes for Bioactive Compounds: Past, Present, and Future Trends

Chiral ligand-exchange high-performance liquid chromatography with copper (II)-L-phenylalanine complexes for separation of 3,4-dimethoxy-α-methylphenylalanine racemes

Chiral separation of α-cyclohexylmandelic acid enantiomers using ionic liquid/salt aqueous two-phase system

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