Chiral separation of pyrethroic acids with single isomer permethyl monoamino β-cyclodextrin selector

Iványi, Róbert; Jicsinszky, László; Juvancz, Zoltán

doi:10.1002/1522-2683(200109)22:15<3232::aid-elps3232>3.0.co;2-g

Cited by 20 publications

(12 citation statements)

References 12 publications

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“…The GC results suggested that the β ring size also has chiral selectivity features toward pyrethroic acids on CE. The pyrethroic acid enantiomers have been effectively separated with various derivatives of β-CD in capillary electrophoresis [19][20][21]. Their chiral separations were possible with several neutral and positively chargeable CD derivatives.…”

Section: Results Of Capillary Electrophoresis (Ce) Measurementsmentioning

confidence: 99%

“…The enantiomer selective analyses of pyrethroic acids are also important from the point of view of production processes and metabolism control in the environment. The GC [17], SFC [18], or capillary electrophoresis (CE) methods [19][20][21] are very useful in the chiral analysis of pyrethroic acids. Several chiral separations, however, remain unsolved in the field, particularly in the production of pyrethroids.…”

Section: Pyrethroidsmentioning

confidence: 99%

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Chiral Separations of Pyrethroic Acids Using Cyclodextrin Selectors

et al. 2022

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Pyrethroid insecticides are broadly used. They have low toxicity for warm-blooded living creatures, but high toxicity for both insects and fish. Therefore, it is important to reduce the environmental impact of pyrethroids. Pyrethroic acids are chiral compounds. An effective way to decrease pollution is to use enantio-pure insecticide products instead of their racemic mixtures. Enantiomer-pure products require enantiomer selective synthesis and analysis. The chiral selective analysis of pyrethroic acids (an intermediate of pyrethroids) is also important in terms of process control and from the point of view of their degradation metabolism in the environment. This study used various enantiomeric selective chromatographic methods for the separation of different pyrethroic acids, including gas chromatography, supercritical fluid chromatography and capillary electrophoresis. Systematic experiments were conducted to find the optimum conditions for their chiral separation. The employed enantio-selective agents were cyclodextrin derivatives with different ring sizes and substitution patterns. The β-cyclodextrin proved to be excellent for the chiral separation of these acids. The different chiral recognition mechanisms were established using different ring-sized cyclodextrins. The results of these systematic studies demonstrated the correlations of the chiral selectivity features of selectors and the structures of analytes.

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Section: Results Of Capillary Electrophoresis (Ce) Measurementsmentioning

confidence: 99%

Section: Pyrethroidsmentioning

confidence: 99%

Chiral Separations of Pyrethroic Acids Using Cyclodextrin Selectors

et al. 2022

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“…Such statistically derivatized CDs have reduced batch to batch reproducibility. An alternative synthesis produces a single isomeric derivative where the product has only one fixed structure [21,22]. These single isomeric CD derivatives show well-defined characteristics with excellent batch to batch reproducibility.…”

Section: Physical and Chemical Characterization Of Cyclodextrinsmentioning

confidence: 99%

“…Recently the charged CDs become more and more popular [13,15,21,25,64,84]. Sometimes a 0.5 mM ionized CD chiral selector is enough for baseline separation of oppositely charged enantiomers (Fig.…”

Section: Application Of Cyclodextrins In Capillary Electrophoresismentioning

confidence: 99%

Cyclodextrins as Dominant Chiral Selective Agents in the Capillary Separation Techniques

Juvancz

Bodáné-Kendrovics

Szente

et al. 2021

Period. Polytech. Chem. Eng.

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This review paper shows the dominant role of the cyclodextrins in the chiral separations using capillary columns (GC, SFC, CE). The cyclodextrins (CDs) have extremely broad chiral selectivity spectra because they have several different chiral recognition sites in various arrangements and various interaction modes. Their chiral selectivity features can further improve with their various substitutions. Their selectivities are moderate therefore they need high efficiency separations (capillary columns) for good chiral resolutions. The shape selectivity of cyclodextrins is also shown with non-chiral isomers too. The utility of the cyclodextrins is demonstrated with several examples based on the personal observations of authors and critical review of literature. The theoretical backgrounds of their chiral recognitions (e.g. H-bond interaction, inclusion, induced fit) are discussed in depth. This paper is not application oriented but is dealing with mostly on the physical and chemical background of separations using CDs.

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“…All of them have shown the possibilities of these CDs to perform the enantiomeric separation of analytes in pharmaceutical analysis, being the most common application the separation of carboxylic acids or amino acids. Only in five studies, besides drugs, phenoxy acid herbicides [7, 8, 29 and 30], and pyrethroic acids [31] were enantioseparated.…”

Section: Introductionmentioning

confidence: 99%

Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresis

2003

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Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresisCharged cyclodextrin (CD) derivatives were used as chiral selectors in electrokinetic chromatography (EKC) for the chiral separation of highly hydrophobic neutral racemates such as atropisomeric polychlorinated biphenyls (PCBs). b-CD-phosphated, b-CD sulfated, succinylated-g-CD (Succ-g-CD) and succinylated-b-CD (Succ-b-CD) were used as anionic CDs. As cationic CD, 6-monodeoxy-6-monoamino-b-CD (b-CD-NH 2 ) was tested for the first time in order to separate PCBs. From the different CD derivatives employed, the best separations were obtained with the cationic CD derivative. Thus, the use of b-CD-NH 2 in phosphate buffer at pH 2.0 containing urea allowed the chiral recognition of eleven PCBs (45, 84, 88, 91, 95, 131, 136, 144, 149, 176, and 197). In this case, the addition of 2 M urea to the buffer solution was crucial to achieve the chiral separation of PCBs. The addition of acetonitrile to 10 mM phosphate buffer (pH 2.0) with 30 mM b-CD-NH 2 and 2 M urea improved considerably the chiral resolution obtained for PCBs 91, 95, 136, 144, 149, and 197 although an increase in the analysis time was also observed. All the results obtained were compared with those previously obtained with the dual CD system carboxymethyl-g-CD/b-CD.

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Chiral separation of pyrethroic acids with single isomer permethyl monoamino β-cyclodextrin selector

Cited by 20 publications

References 12 publications

Chiral Separations of Pyrethroic Acids Using Cyclodextrin Selectors

Chiral Separations of Pyrethroic Acids Using Cyclodextrin Selectors

Cyclodextrins as Dominant Chiral Selective Agents in the Capillary Separation Techniques

Comparison of charged cyclodextrin derivatives for the chiral separation of atropisomeric polychlorinated biphenyls by capillary electrophoresis

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