Enantioseparation and Enantioselective Analysis of Chiral Herbicides

Jin, Lixia; Gao, Weiliang; Li, Ling; Ye, Jing; Lin, Chunmian; Liu, Weiping

doi:10.5772/13563

Cited by 3 publications

(3 citation statements)

References 83 publications

(100 reference statements)

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“…Polysaccharide derivative-based CSs based on cellulose and amylose can nowadays separate about 90% of the tested racemic compounds and enantiomeric mixtures (Ikai and Okamoto 2009;Shen and Okamoto 2016;Yin et al 2019). Important fields of enantioseparation are, inter alia, stereoselective synthesis (Chebrouk et al 2019;D'Orazio 2020;Shi et al 2020), the analysis of enantiomers in food products (Fanali et al 2019;Alvarez-Rivera et al 2020), fungicides (Ying et al 2009;Ruiz-Rodríguez et al 2015;Wang et al 2021b), herbicides (Martín-Biosca et al 2001;Lao and Gan 2006;Jin et al 2010), insecticides (Zhang et al 2016;Zhao et al 2019), pesticides (Carrão et al 2019;Merino et al 2019;Li et al 2022), and-very importantly-pharmaceutical products (Mukherjee and Bera 2012;Yaling and Alex 2013;Singh et al 2020).…”

Section: Introductionmentioning

confidence: 99%

Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Bui

Rosenau

2022

Cellulose

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A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors and the subsequent mild immobilization onto pre-functionalized silica gel are introduced, utilizing Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition (“click”) chemistry. A cellulose 3,5-dimethylphenyl carbamate derivative carrying propynyl carbamate groups was prepared by a combination of carbonate aminolysis and isocyanate chemistry. For immobilization, 3-azidopropyl-functionalized silica gel as an inert carrier was used, synthesized via a 3-chloropropyl intermediate. The chiral selector, as well as the inorganic/organic hybrid materials (silica gel/chiral selector), were comprehensively characterized by ATR-FTIR, solid-state 13C and 29Si NMR, liquid-state NMR, GPC, TGA, and elemental analysis. The enantioseparation performance of the immobilized-type chiral stationary phase was evaluated by HPLC with a set of representative chiral test analytes and different eluents and compared to a respective coated-type (=non-covalently bound) chiral stationary phase carrying the same selector quality and quantity on the same silica gel matrix. The immobilization did not adversely affect the chiral separation performance; on the contrary, in some chromatographic separations the immobilized-type chiral stationary phase surprisingly even surpassed the coated reference material. Graphical abstract

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Section: Introductionmentioning

confidence: 99%

Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Bui

Rosenau

2022

Cellulose

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“…Also, a sustained increase in the development of chiral drugs in pharmaceutical industries has begun since three decades ago, the main motivation is that when a patent on racemic drug expires, pharmaceutical companies have the opportunity to extend its rights through the development of the chiral switch to the enantiomer with the desired activity . At the same time, the new policy statements issued by the regulatory agencies promoted that new chiral drugs have to be produced in enantiomerically enriched pure forms and the trends in the agrochemical industries are somewhat similar . All these policies caused a significant change in the way the production plants are managed .…”

Section: Introductionmentioning

confidence: 99%

“…At the same time, the new policy statements issued by the regulatory agencies promoted that new chiral Correspondence: Prof. C. B. Castells, LIDMA (Laboratorio de Investigación y Desarrollo de Métodos Analíticos) y División Química Analítica, Universidad Nacional de La Plata, 47 y 115 (1900) La Plata, Argentina. E-mail: castells@isis.unlp.edu.ar Abbreviations: PARAFAC, parallel factor analysis; PRESS, predicted error sum of squares; RMSEP, root mean square error of prediction; U-PLS, unfolded partial least-squares drugs have to be produced in enantiomerically enriched pure forms [3] and the trends in the agrochemical industries are somewhat similar [4]. All these policies caused a significant change in the way the production plants are managed [5].…”

Section: Introductionmentioning

confidence: 99%

Scope of partial least‐squares regression applied to the enantiomeric composition determination of ketoprofen from strongly overlapped chromatographic profiles

Padró

Osorio-Grisales

Arancibia

et al. 2015

J of Separation Science

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Valuable quantitative information could be obtained from strongly overlapped chromatographic profiles of two enantiomers by using proper chemometric methods.Complete separation profiles where the peaks are fully resolved are difficult to achieve in chiral separation methods, and this becomes a particularly severe problem in case that the analyst need to measure the chiral purity, i.e., when one of the enantiomers is present in the sample in very low concentrations. In this report, we explore the scope of a multivariate chemometric technique based on unfolded partial least-squares regression, as a mathematical tool to solve this quite frequent difficulty. This technique was applied to obtain quantitative results from partially overlapped chromatographic profiles of R-and S-ketoprofen, with different values of enantioresolution factors (from 0.81 down to less than 0.2 resolution units), and also at several different S:R enantiomeric ratios. Enantiomeric purity below 1% was determined with excellent precision even from almost completely overlapped signals. All these assays were tested on the most demanding condition, i.e., when the minor peak elutes immediately after the main peak. The results were validated using univariate calibration of completely resolved profiles and the method applied to the determination of enantiomeric purity of commercial pharmaceuticals.

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Separation of para- and meta-Imazamethabenz-methyl Enantiomers by Direct Chiral HPLC Using a Protein Chiral Selector

et al. 2012

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Enantioseparation and Enantioselective Analysis of Chiral Herbicides

Cited by 3 publications

References 83 publications

Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Scope of partial least‐squares regression applied to the enantiomeric composition determination of ketoprofen from strongly overlapped chromatographic profiles

Separation of para- and meta-Imazamethabenz-methyl Enantiomers by Direct Chiral HPLC Using a Protein Chiral Selector

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