HPLC Enantioseparation of Novel Spirobrassinin Analogs on the Cyclofructan Chiral Stationary Phases

Moskalova, M.A.; Kozlov, Oleksandr; Gondová, Taťána; Budovská, Mariana; Armstrong, Daniel W.

doi:10.1007/s10337-016-3212-z

Cited by 13 publications

(11 citation statements)

References 26 publications

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“…A good linearities of Van't Hoff plots were found for the enantiomers over a temperature at the range of 20-40 °C with R 2 ranging from 0.8477 to 0.9996. As the calculated ΔH, ΔS 0 , ΔΔH 0 and ΔΔS 0 values shown in Table 2, the negative ΔH values present that the transfer of the enantiomers from the mobile phase to the stationary phase was driven by enthalpy; the negative ΔΔH 0 and ΔΔS 0 values illustrated the separation factor of the fenobucarb individuals was driven by enthalpy when the temperature below T iso [23]. A temperature of 20 °C was chosen for an effective enantioselective determination.…”

Section: Optimization Of Chromatographic Conditionmentioning

confidence: 99%

Simultaneous separation and detection chiral fenobucarb enantiomers using UPLC–MS/MS

Xia

et al. 2019

SN Appl. Sci.

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A reliable and sensitive method was developed and validated for the determination of chiral pesticide fenobucarb enantiomers with UPLC-MS/MS. The fenobucarb enantiomers were baseline separated on Daicel IG-3 chiral column using a mixture of acetonitrile and 0.1% formic acid water (60:40, v/v) as mobile phase. The absolute configuration of fenobucarb enantiomers was confirmed as (R)-(+)-fenobucarb and (S)-(−)-fenobucarb by experimental and calculated electronic circular dichroism spectra. Good linearity (R 2 > 0.9962) was obtained for the four matrix calibration curves within the range of 0.5-50 μg mL −1 . The limit of detection of the two enantiomers were in the range of 0.07-0.16 μg L −1 . The mean recoveries of the two enantiomers ranged from 80.4 to 102% with intra-day relative standard deviations (RSDs) from 1.8 to 6.6% and inter-day RSDs from 3.0 to 5.7% in four matrices. The (R)-(+)-fenobucarb degraded faster than (S)-(−)-isomer in cucumber. The established method can provide additional information for the further research about the enantioselective environmental behaviors of fenobucarb.

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Section: Optimization Of Chromatographic Conditionmentioning

confidence: 99%

Simultaneous separation and detection chiral fenobucarb enantiomers using UPLC–MS/MS

Xia

et al. 2019

SN Appl. Sci.

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“…Commonly used commercially available cyclofructan columns are isopropyl carbamate cyclofructan-6, R -naphthylethyl-cyclofructan-6 and dimethylphenyl-cyclofructan-7, and these cyclofructose columns have been shown to be useful for the separation of multiple enantiomers. Compared with polysaccharide-derived CSPs, these have a lower operating temperature, a higher mobile phase flow rate, and a wider range of mobile phase types [ 24 , 26 , 27 ]. Regarding the expansion of the application field of cyclofructan CSPs and the improvement of their chiral recognition ability, the main directions in recent years have been the diversification of substituents during derivatization and the application of superficially porous particles.…”

Section: Chromatographic Separationmentioning

confidence: 99%

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

et al. 2021

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With the rapid development of global industry and increasingly frequent product circulation, the separation and detection of chiral drugs/pesticides are becoming increasingly important. The chiral nature of substances can result in harm to the human body, and the selective endocrine-disrupting effect of drug enantiomers is caused by differential enantiospecific binding to receptors. This review is devoted to the specific recognition and resolution of chiral molecules by chromatography and membrane-based enantioseparation techniques. Chromatographic enantiomer separations with chiral stationary phase (CSP)-based columns and membrane-based enantiomer filtration are detailed. In addition, the unique properties of these chiral resolution methods have been summarized for practical applications in the chemistry, environment, biology, medicine, and food industries. We further discussed the recognition mechanism in analytical enantioseparations and analyzed recent developments and future prospects of chromatographic and membrane-based enantioseparations.

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“…The effects of mobile phase composition on the enantioseparation of nine analogs of spirobrassinin were evaluated in NP mode [ 54 ]. Among the commercially available Larihc columns, that derivatized with the R -naphthylethyl carbamate moiety provided the best separations for the studied analogs due to stronger π–π interactions.…”

Section: Recent Applications Of Cyclofructan-based Cspsmentioning

confidence: 99%

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

et al. 2021

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Natural compounds can exist in different forms, where molecules possessing chirality play an essential role in living organisms. Currently, one of the most important tasks of modern analytical chemistry is the enantioseparation of chiral compounds, in particular, the enantiomers of compounds having biological and/or pharmaceutical activity. Whether the task is to analyze environmental or food samples or to develop an assay for drug control, well-reproducible, highly sensitive, stereoselective, and robust methods are required. High-performance liquid chromatography best meets these conditions. Nevertheless, in many cases, gas chromatography, supercritical fluid chromatography, or capillary electrophoresis can also offer a suitable solution. Amino acids, proteins, cyclodextrins, derivatized polysaccharides, macrocyclic glycopeptides, and ion exchangers can serve as efficient selectors in liquid chromatography, and they are quite frequently applied and reviewed. Crown ethers and cyclofructans possessing similar structural characteristics and selectivity in the enantiodiscrimination of different amine compounds are discussed less frequently. This review collects information on enantioseparations achieved recently with the use of chiral stationary phases based on crown ethers or cyclofructans, focusing on liquid chromatographic applications.

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HPLC Enantioseparation of Novel Spirobrassinin Analogs on the Cyclofructan Chiral Stationary Phases

Cited by 13 publications

References 26 publications

Simultaneous separation and detection chiral fenobucarb enantiomers using UPLC–MS/MS

Simultaneous separation and detection chiral fenobucarb enantiomers using UPLC–MS/MS

Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects

Liquid Chromatographic Enantioseparations Utilizing Chiral Stationary Phases Based on Crown Ethers and Cyclofructans

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