Isoleucine ionic liquids as additives to separate mandelic acid and their derivative enantiomers by HPLC

Zhou, Jie; Zhao, S. J.; Fu, Guangjun; Zhang, Zhenzhong

doi:10.1039/c3ay41669k

Cited by 14 publications

(7 citation statements)

References 20 publications

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“…The numbers of theoretical plates were calculated to be 3.2 × 10 3 and 5.4 × 10 3 plates/m for S-mandelic acid and R-mandelic acid on the MIP-Fe 3 O 4 @PNE NPs modified PDMS microchip, respectively. The resolution factor (Rs) was 1.82, which is much better than that of 1.29 on substituted ␤-cyclodextrin as chiral mobile phase [36] and 1.62 using isoleucine ionic liquids as additives to separate mandelic acid by high performance liquid chromatography (HPLC) [37], and 1.52 by ligandexchange capillary electrophoresis using N-(2-hydroxyoctyl)-L-4-hydroxyproline-copper(II) complex as chiral selector [38], while lower than 5.04 using glycopeptide as chiral stationary phase in capillary electrochromatography (CEC) [39]. In order to further prove the usefulness of the proposed imprinting strategy, the MIP-Fe 3 O 4 @PNE NPs were also used to modify PDMS microchip using S-mandelic acid as template molecule (curve d).…”

Section: Separation Of Chiral Compoundsmentioning

confidence: 99%

Separation of chiral compounds using magnetic molecularly imprinted polymer nanoparticles as stationary phase by microchip capillary electrochromatography

Liang

Chen

et al. 2017

Electrophoresis

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In this work, a simple and rapid approach was developed for separation and detection of chiral compounds based on a magnetic molecularly imprinted polymer modified poly(dimethylsiloxane) (PDMS) microchip coupled with electrochemical detection. Molecularly imprinted polymers were prepared employing Fe O nanoparticles (NPs) as the supporting substrate and norepinephrine as the functional monomer in the presence of template molecule in a weak alkaline solution. After extracting the embedded template molecules, Fe O @polynorepinephrine NPs (MIP-Fe O @PNE NPs) showed specific molecular recognition selectivity and high affinity towards the template molecule, which were then used as stationary phase of microchip capillary electrochromatography for chiral compounds separation. Mandelic acid and histidine enantiomers were used as model compounds to test the chiral stationary phase. By using R-mandelic acid as the template molecule, mandelic acid enantiomer was effectively separated and detected on the MIP-Fe O @PNE NPs modified PDMS microchip. Moreover, the successful separation of histidine enantiomers on the MIP-Fe O @PNE NPs modified microchip using L-histidine as template molecule was also achieved.

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Section: Separation Of Chiral Compoundsmentioning

confidence: 99%

Separation of chiral compounds using magnetic molecularly imprinted polymer nanoparticles as stationary phase by microchip capillary electrochromatography

Liang

Chen

et al. 2017

Electrophoresis

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“…Amino acid ionic liquids (AAILs) are one kind of RTILs which were first synthesized by Ohno et al. in 2005 , and have received widely concerned due to its better properties of environmental friendliness, biocompatibility, biodegradability, simple synthetic method, hand sexual selectivity, etc. AAILs with specific functions can be synthesized by modifying or altering the amino acid side chain substituents.…”

Section: Introductionmentioning

confidence: 99%

“…RTILs such as imidazole ionic liquids have the characters of low vapor pressure, non-volatility, good thermal stability and chemical stability, and have been widely used as stationary phase modifiers [21] and mobile phase modifiers [22]. Amino acid ionic liquids (AAILs) are one kind of RTILs which were first synthesized by Ohno et al in 2005 [23], and have received widely concerned [24][25][26][27][28] due to its better properties of environmental friendliness, biocompatibility, biodegradability, simple syn-thetic method, hand sexual selectivity, etc. AAILs with specific functions can be synthesized by modifying or altering the amino acid side chain substituents.…”

Section: Introductionmentioning

confidence: 99%

Use of an amino acid ionic liquid as an ion exchange chromatography mobile phase modifier for the analysis of magnesium, calcium, zinc, and iron ions

Liu

et al. 2018

Separation Science Plus

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Four acids were used as the mobile phase of ion exchange chromatography to analyze magnesium, calcium, zinc, and iron ions, and nitric acid showed the best character. The amino acid ionic liquid was then added to the mobile phase to analyze its effect on the retention time, peak height and resolution of detected cations. When the imidazole glycine ionic liquid was used, the retention time was reduced, peak shape was improved, resolution of analytes was optimized and the detect limit was reduced effectively. The optimum conditions of this experiment were that adding 0.10 mM imidazole glycine ionic liquid to mobile phase and the flow rate of mobile phase was 0.8 mL·min−1 at room temperature. Under these conditions, the peak area was proportional to the concentration of cations, and the linear equations of the magnesium, calcium, zinc, iron ions were S = 0.0126 + 4.4463 C, S = –0.0452 + 3.9224 C, S = –0.0241 + 7.461 C, and S = –0.0213 + 6.3154 C, and the detection limits of four ions were 0.96, 3.58, 2.12, 0.57 μg·L−1 respectively. Furthermore, this method was successfully applied in determining cations in actual samples.

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“…). Although there are several studies about the enantioseparation of mandelic acid derivatives in HPLC , no report is available about the enantioseparation of 4‐methoxymandelic, 3‐chloromandelic acid, 4‐bromomandelic acid, α‐cyclopentylmandelic acid, and α‐cyclohexylmandelic acid with a chiral ligand exchange mobile phase. And only one paper is available that is about the enantioseparation of 4‐hydroxy‐3‐methoxymandelic acid and 4‐hydroxymandelic acid using copper(II)– N , N ‐di‐ n ‐propyl‐ l ‐alanine complexes as a chiral mobile phase additive .…”

Section: Introductionmentioning

confidence: 99%

Modeling the retention mechanism for high-performance liquid chromatography with a chiral ligand mobile phase and enantioseparation of mandelic acid derivatives

et al. 2015

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The chromatographic retention mechanism describing relationship between retention factor and concentration of Cu(2+) (l-phenylalanine)2 using chiral ligand mobile phase was investigated and eight mandelic acid derivatives were enantioseparated by chiral ligand exchange chromatography. The relationship between retention factor and concentration of the Cu(2+) (l-phenylalanine)2 complex was proven to be in conformity with chromatographic retention mechanism in which chiral discrimination occurred both in mobile and stationary phase. Different copper(II) salts, chiral ligands, organic modifier, pH of aqueous phase, and conventional temperature on retention behavior were optimized. Eight racemates were successfully enantioseparated on a common reversed-phase column with an optimized mobile phase composed of 6 mmol/L of l-phenylalanine or N,N-dimethyl-l-phenylalanine and 3 mmol/Lof copper(II) acetate or copper(II) sulfate aqueous solution and methanol.

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Isoleucine ionic liquids as additives to separate mandelic acid and their derivative enantiomers by HPLC

Abstract: In this study, functional isoleucine ionic liquids were synthesized and used as novel chiral ligands coordinated with Cu(ii) in chiral ligand exchange chromatography.

Cited by 14 publications

References 20 publications

Separation of chiral compounds using magnetic molecularly imprinted polymer nanoparticles as stationary phase by microchip capillary electrochromatography

Separation of chiral compounds using magnetic molecularly imprinted polymer nanoparticles as stationary phase by microchip capillary electrochromatography

Use of an amino acid ionic liquid as an ion exchange chromatography mobile phase modifier for the analysis of magnesium, calcium, zinc, and iron ions

Modeling the retention mechanism for high-performance liquid chromatography with a chiral ligand mobile phase and enantioseparation of mandelic acid derivatives

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