Separation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide-Based Coated Chiral Stationary Phases

Upmanis, Toms; Kažoka, H.; Орлова, Н. А.; Vorona, M.

doi:10.1007/s10337-020-03862-7

Cited by 6 publications

(3 citation statements)

References 18 publications

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“…The performance of the CSPs depends on both the backbones and the side chains of the polymer. The polar carbamate groups of the side chains play an important role in chiral recognition [28]. In this study, given that better peak shape of oxathiapiprolin enantiomers was obtained by the cellulose‐2 column, it was thus selected for further optimization.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation and dissipation monitoring of oxathiapiprolin in grape using supercritical fluid chromatography tandem mass spectrometry

Liu

Dong

et al. 2020

J of Separation Science

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Oxathiapiprolin is a chiral fungicide used in China for the prevention and treatment of grape downy mildew, but its potential risk could be inaccurately assessed without distinguishing its enantiomers. In this study, an effective and sensitive chiral analytical method was first established for quantification of oxathiapiprolin enantiomers using supercritical fluid chromatography tandem mass spectrometry. Baseline separation for oxathiapiprolin enantiomers was achieved for less than 3 min by using a Lux Cellulose‐2 chiral column with the resolution of 1.51. The elution order of the eluting enantiomers was identified as (−)‐oxathiapiprolin and (+)‐oxathiapiprolin by an optical rotation detector. The grape samples were extracted by QuEChERS method, with the average recoveries of each enantiomer in grapes were in the range of 88.1–111.8% and the relative standard deviations were less than 18.9%. The enantioselective analysis of the dissipation of oxathiapiprolin in field grape samples showed that (−)‐oxathiapiprolin was dissipated faster than (+)‐oxathiapiprolin. The results indicate that this proposed method could provide data support for the risk assessment of oxathiapiprolin in agricultural produces in a more accurate way.

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Section: Resultsmentioning

confidence: 99%

Enantioseparation and dissipation monitoring of oxathiapiprolin in grape using supercritical fluid chromatography tandem mass spectrometry

Liu

Dong

et al. 2020

J of Separation Science

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“…These interactions are also addressed when the enantiomer discrimination ability between different polysaccharide derivatives as CSs is compared. Upmanis et al [ 48 ] reported an extensive study using the six commercial chiral columns Lux ® Amylose-1, Lux ® Amylose-2 ( Table 2 ), Lux ® Cellulose-1, Lux ® Cellulose-2, Lux ® Cellulose-3, and Lux ® Cellulose-4 ( Table 1 ) (150 × 4.6 mm, i.d., 5 μm silica gel for all the columns), under normal and polar organic mobile-phase conditions in HPLC for the ES of 15 structurally different 4C-substituted pyrrolidin-2-one derivatives ( Supplementary Materials Figure S18 ).…”

Section: Amylose-based Cspsmentioning

confidence: 99%

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Bui

Rosenau

2021

Molecules

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Polysaccharides, oligosaccharides, and their derivatives, particularly of amylose, cellulose, chitosan, and β-cyclodextrin, are well-known chiral selectors (CSs) of chiral stationary phases (CSPs) in chromatography, because they can separate a wide range of enantiomers. Typically, such CSPs are prepared by physically coating, or chemically immobilizing the polysaccharide and β-cyclodextrin derivatives onto inert silica gel carriers as chromatographic support. Over the past few years, new chiral selectors have been introduced, and progressive methods to prepare CSPs have been exploited. Also, chiral recognition mechanisms, which play a crucial role in the investigation of chiral separations, have been better elucidated. Further insights into the broad functional performance of commercially available chiral column materials and/or the respective newly developed chiral phase materials on enantiomeric separation (ES) have been gained. This review summarizes the recent developments in CSs, CSP preparation, chiral recognition mechanisms, and enantiomeric separation methods, based on polysaccharides and β-cyclodextrins as CSs, with a focus on the years 2019–2020 of this rapidly developing field.

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“…Chromatographic enantioseparation, particularly by HPLC using chiral stationary phases (CSPs), has been recognized as one of the most efficient approaches applicable not only for analyzing enantiomers, but also for obtaining pure optical enantiomers. Due to their broad applicability to many structurally diverse chiral compounds, polysaccharide derivatives are the most popular CSPs in HPLC [1][2][3][4][5][6]. Among them, homoge-Article Related Abbreviations: CPM, chiral packing material; CSP, chiral stationary phase; CTCMPC, cellulose tris(3-chloro-4-methylphenylcarbamate); DMA, N,N-dimethylacetamide; TGA, thermogravimetric analysis; TrCl, triphenylmethyl chloride neously substituted benzoates and phenylcarbamates of cellulose and amylose are the most often used materials, that is, they have the same substituent at the 2-, 3-, and 6-positions of a glucose unit.…”

Section: Introductionmentioning

confidence: 99%

Enantiomer separation on novel cellulose derivatives bearing regioselective phenylcarbamate groups

Tang

Wang

Yan

et al. 2020

J of Separation Science

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Four novel regioselectively carbamoylated cellulose derivatives with two types of substituents, one being a 3‐chloro‐4‐methylphenylcarbamate group and the other being a phenylcarbamate, a 3,5‐dichlorophenylcarbamate or a 4‐methylphenylcarbamate group, at the 2‐, 3‐positions and 6‐position were synthesized and utilized as chiral stationary phases in high‐performance liquid chromatography. The obtained derivatives exhibited characteristic chiral recognition abilities which were significantly affected by the nature and arrangement of the groups at the 2‐, 3‐positions and 6‐position. Compared with cellulose tris(3‐chloro‐4‐methylphenylcarbamate) and Chiralcel OD columns, several racemates were better resolved on these new phases. With all six racemates resolved on cellulose 2,3‐bis(4‐methylphenylcarbamate)‐6‐(3‐chloro‐4‐methylphenylcarbamate), it appears to be a potential useful chiral stationary phase in the future. Also, the influence of mobile phase on chiral recognition was investigated. Better resolutions were generally obtained with decreased amount of 2‐propanol with a mixture of hexane/2‐propanol as the mobile phase. Moreover, when ethanol was used instead of 2‐propanol as the mobile phase modifier, poorer enantioseparations were often achieved.

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Separation of 4C-Substituted Pyrrolidin-2-One Derivatives on Polysaccharide-Based Coated Chiral Stationary Phases

Cited by 6 publications

References 18 publications

Enantioseparation and dissipation monitoring of oxathiapiprolin in grape using supercritical fluid chromatography tandem mass spectrometry

Enantioseparation and dissipation monitoring of oxathiapiprolin in grape using supercritical fluid chromatography tandem mass spectrometry

Polysaccharide- and β-Cyclodextrin-Based Chiral Selectors for Enantiomer Resolution: Recent Developments and Applications

Enantiomer separation on novel cellulose derivatives bearing regioselective phenylcarbamate groups

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