Chiral Speciation and Determination of dl-Selenomethionine Enantiomers on a Novel Chiral Ligand-Exchange Stationary Phase

Huang, Xiaojia; Wang, Junde; Wang, Qiuquan; Huang, Benli

doi:10.2116/analsci.21.253

Cited by 27 publications

(15 citation statements)

References 33 publications

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“…In fact, it is believed that it has health benefits at low concentrations, whereas at higher concentrations it becomes toxic (causing problems such as dermatitis, fatigue, and hair loss ), being the range among deficiency, essentiality, and toxicity, very narrow . Selenium deficiency is associated with serious nutritional and health problems such as hypertension, infertility, arthritis and ageing, and different types of cancer, among others .…”

Section: Introductionmentioning

confidence: 99%

A micellar electrokinetic chromatography approach using diastereomeric derivatization and a volatile surfactant for the enantioselective separation of selenomethionine

2019

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A MEKC methodology with UV detection was developed for the enantioselective separation of selenomethionine (SeMet). The use of (+)‐1‐(9‐fluorenyl)ethyl chloroformate (FLEC) as chiral derivatization reagent to form SeMet diastereomers enabled their subsequent separation using ammonium perfluorooctanoate (APFO) as a volatile pseudostationary phase. The effect of APFO concentration and pH, temperature, injection volume, and derivatization conditions (time and FLEC/SeMet ratio) were evaluated in order to select the best separation conditions. A chiral resolution of 4.4 for DL‐SeMet was achieved in less than 6 min using 100 mM APFO at pH 8.5 as electrophoretic buffer. Satisfactory results were obtained in terms of linearity, precision (RSD from 3.4 to 5.1% for migration times and from 1.8 to 4.6% for corrected peak areas), accuracy, and LODs (3.1 × 10−6 M and 3.7 × 10−6 M for d and l enantiomers, respectively). The method was successfully applied to the determination of l‐SeMet in food supplements.

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Section: Introductionmentioning

confidence: 99%

A micellar electrokinetic chromatography approach using diastereomeric derivatization and a volatile surfactant for the enantioselective separation of selenomethionine

2019

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“…Up until now, the enantiomeric resolution is still the major method for obtaining the single enantiomer. Many methods are used for the enantioseparation of enantiomers, including chemical resolution [1], chromatographic (such as thin-layer chromatography [2], liquid chromatography [3], gas chromatography [4], and capillary electrophoresis [5], et al), enzymatic or microbiological methods [6,7], membranous resolution [8], various extraction methods (such as liquid-liquid extraction [9], solid-liquid two-phase system [10], magnetic solid-phase extraction [11], and ligand exchange extraction [12]), and the metal-organic frameworks (MOFs) method [13]. Among these methods, the chiral liquid-liquid extraction is simple, low cost, and easy to scale up [14,15].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective Extraction of Phenylalanine Enantiomers Using Environmentally Friendly Aqueous Two-Phase Systems

Sun

Wang

et al. 2018

Processes

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(1) Background: The environmentally friendly choline-amino acid ionic liquids (ChAAILs) and deep eutectic solvents (DESs) have been used as excellent alternatives to volatile organic compounds (VOCs) and ionic liquids (ILs) in recent years; (2) Methods: Thus, ChAAILs/salt and DESs/salt aqueous two-phase systems (ATPSs) were developed for the chiral extraction of phenylalanine enantiomers. The optimum ATPS of [Ch][L-Pro]/K3PO4 was chosen, and the influencing parameters were investigated, including ChAAILs concentration, salt concentration, chiral selector concentration, extraction temperature, phenylalanine concentration, and system pH; (3) Results: The phenylalanine enantiomers were mainly extracted into the top phase (ChAAIL-rich phase), meanwhile, the (S)-phenylalanine [(S)-Phe)] was preferentially recognized by the chiral selector in the top phase. The maximum separation factor (α) of 2.05 was obtained under the optimal conditions; and (4) Conclusions: This ATPS that was used for the chiral extraction of enantiomers is much more environmentally friendly, simple, and rapid, and has the potential to be used in the enantioselective extraction of other enantiomers.

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“…Among these, it is worth mentioning the amino acids proline, hydroxyproline (Davankov and Kurganov, 1983;Yamskov et al, 1981), cysteine (Natalini et al, , 2008b(Natalini et al, , 2008c, histidine Watanabe, 1983), phenylalanine (Wan et al, 1997;Wernicke, 1995), alanine (Tsvetkov and Mingelgrin, 1987), lysine (Tsvetkov and Mingelgrin, 1987), isoleucine (Huang et al, 2005), and penicillamine (Ôi et al, 1995), and few amino alcohols carrying a phenylglycinol (Hyun et al, 2003(Hyun et al, , 2004, leucinol (Hyun and Ryoo, 1996;Hyun et al, 2002), or pyrrolidinemethanol (Natalini et al, 2007) residual as the basic scaffold.…”

Section: Introductionmentioning

confidence: 99%

S-Trityl-(R)-Cysteine, a Multipurpose Chiral Selector for Ligand-Exchange Liquid Chromatography Applications

Sardella

Ianni

Lisanti

et al. 2015

Critical Reviews in Analytical Chemistry

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The stratification of 0.040-0.050 g of S-trityl-(R)-cysteine ((R)-STC) onto a conventional ODS phase produces a very effective (α and RS up to 5.71 and 12.09, respectively) and stable (more than 30 days of repeated analysis) chiral ligand-exchange chromatography (CLEC) coated chiral stationary phase (C-CSP). With a few specific exceptions, a (R) < (S) enantiomer elution order can be easily predicted. The (R)-STC-based C-CSP can be successfully exploited also at a preparative level for enantioisolations of CNS active amino acids (AAs), with a racemate loadability up to 0.015 g for single injection. The CLEC (R)-STC-based system can be helpful in monitoring the presence of (R)-AAs in edible products and other organic materials, thus contributing to evaluating product quality and diagnosing subclinical pathological states in animals and humans. Very profitably, molecular modeling-based computer-assisted classification analyses can reveal the actual enantioseparation ability of the (R)-STC phase towards a specific compound.

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Chiral Speciation and Determination of dl-Selenomethionine Enantiomers on a Novel Chiral Ligand-Exchange Stationary Phase

Cited by 27 publications

References 33 publications

A micellar electrokinetic chromatography approach using diastereomeric derivatization and a volatile surfactant for the enantioselective separation of selenomethionine

A micellar electrokinetic chromatography approach using diastereomeric derivatization and a volatile surfactant for the enantioselective separation of selenomethionine

Enantioselective Extraction of Phenylalanine Enantiomers Using Environmentally Friendly Aqueous Two-Phase Systems

S-Trityl-(R)-Cysteine, a Multipurpose Chiral Selector for Ligand-Exchange Liquid Chromatography Applications

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