Synthesis and application of ionic liquid functionalized β-cyclodextrin, mono-6-deoxy-6-(4-amino-1,2,4-triazolium)-β-cyclodextrin chloride, as chiral selector in capillary electrophoresis

Li, Jingtang; Tao, Yu; Xu, Gelin; Du, Yingxiang; Liu, Zongran; Feng, Zijie; Yang, Xuan; Xi, Ying; Liu, Jie

doi:10.1016/j.chroma.2017.11.068

Cited by 50 publications

(19 citation statements)

References 37 publications

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“…Moreover, in this study the molecular electrostatic potential was calculated for the isolated guest and host molecules. Later, molecular docking was also used to visualize the inclusion complexes of dansyl amino acids and naproxen with mono-6-deoxy-6-(4-amino-1,2,4-triazolium)-β-CD chloride as ionic liquid functionalized CD [174], and of a series of 13 chiral drugs with CM-6-(4-methoxybenzylamino)-β-CD [175].…”

Section: Molecular Modeling Of Capillary Electrophoresis Enantioseparations Promoted By Cyclodextrins: Applicationsmentioning

confidence: 99%

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

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CDs are cyclic oligosaccharides consisting of α‐d‐glucopyranosyl units linked through 1,4‐linkages, which are obtained from enzymatic degradation of starch. The coexistence of hydrophilic and hydrophobic regions in the same structure makes these macrocycles extremely versatile as complexing host with application in food, cosmetics, environmental, agriculture, textile, pharmaceutical, and chemical industries. Due to their inherent chirality, CDs have been also successfully used as chiral selectors in enantioseparation science, in particular, for CE enantioseparations. In the last decades, multidisciplinary approaches based on CE, NMR spectroscopy, X‐ray crystallography, microcalorimetry, and molecular modeling have shed light on some aspects of recognition mechanisms underlying enantiodiscrimination. With the ever growing improvement of computer facilities, hardware and software, computational techniques have become a useful tool to model at molecular level the dynamics of diastereomeric associate formation to sample low‐energy conformations, the binding energies between the enantiomer and the CD, and to profile noncovalent interactions contributing to the stability of CD/enantiomer association. On this basis, the aim of this review is to provide the reader with a critical overview on the applications of CDs in CE. In particular, the contemporary theory of the electrophoretic technique and the main structural features of CDs are described, with a specific focus on techniques, methods, and approaches to model CE enantioseparations promoted by native and substituted CDs. A systematic compilation of all published literature has not been attempted.

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Section: Molecular Modeling Of Capillary Electrophoresis Enantioseparations Promoted By Cyclodextrins: Applicationsmentioning

confidence: 99%

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Peluso

Chankvetadze

2021

Electrophoresis

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“…The obvious superiority of chiral ILs to equal ILs is due to their ability to gain an extra enantiomeric recognition, so separating ability, while maintaining a "system modification" capability [227]. Based on their potential, which is related to ability for recognitions on chiral separations, scientific interest in CILs has warmly increased [228][229][230][231][232][233][234][235][236][237][238][239][240][241][242][243][244][245][246]. In chiral separations studies, it is observed that the performance of the systems created by modifying ionic liquids with SPs enhances the enantiorecognition ability compared to conventional type stationary phases alone [247].…”

Section: Ionıc Liquids (Ils) As Chiral Additivesmentioning

confidence: 99%

Chiral Separations by Capillary Electrophoresis and related Techniques with Different Chiral Selectors: A Review

Şarkaya

Göktürk

Yılmaz

et al. 2021

Hacettepe Journal of Biology and Chemistry

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A nalitik saflıkta ve büyük ölçekli üretim çalışmaları için çözüm yolları bulmaya çalışan farmakoloji ve doğa bilimleriyle ilgilenen araştırmacıların ilgisini kiral bileşiklerin tayin ve enantiyomerik olarak ayrımı konuları çekmiştir. Kapiler Elektroforez, kiral selektörlerin yüksek ayırım gücü ve verimliliği gibi üstün özellikleri nedeniyle enantiyomerik ayırımlar için en önemli analitik yaklaşımlardan biri haline gelmiştir. Yüksek ayırma gücü ve yüksek etkinlik gösterme gibi sahip olduğu üstün özelliklerden dolayı kapiler elektroforez, enantiyomerik ayırmalarda kullanılan en önemli analitik yaklaşımlardan biri haline gelmiştir. Kapiler Elektroforez temeline dayanan teknolojinin gelişim sürecine paralel olarak kiral seçicilerin farklı formlardaki gelişimide süremektedir. Bu derlemede, kapiler elektroforezde kullanılan teknikleri açıklayan bazı tanımlayıcı teorik bilgilere yer verilmiştir. Ayrıca son 10 yılda gerçekleştilen (2010-2020) ve moleküler baskılı polimerler, siklodekstrinler, metal-organik çerçeveler, iyonik sıvılar, nanopartiküller, monolitler gibi farklı kiral seçicilerin ve farklı kiral katkı maddelerin kullanıldığı kiral ayırmalara dayanan çalışmalarda incelenmiştir. Anahtar KelimelerKapiler Elektroforez, kiral selektörler, kiral katkı maddeleri, kiral ayırım.

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“…Other commercially-available modified CDs or laboratory-prepared modified CDs with known synthesis were reported. These were hydroxypropyl-α-CD [23], sulphated-α-CD [21], (2-carboxy-ethyl)-β-CD [34], heptakis(2,3-di- O -acetyl)-β-CD [35], heptakis(2,6-di- O -methyl)-β-CD, heptakis-(2,3,6-tri- O -methyl)-β-CD [36,37], heptakis(2- O -methyl-3,6-di- O -sulfo)-β-CD, heptakis(2,3-di- O -methyl-6- O -sulfo)-β-CD, heptakis(2,3-di- O -acetyl-6- O -sulfo)-β-CD [36], heptakis-6-sulfato-β-CD [38], heptakis-(6- O -sulfobutylether)-β-CD sodium salt [39], heptakis (2,6-di- O -[2-hydroxy-3-(sulfo-amino)propoxy])-β-CD [40], 2-hydroxypropyl-β-CD [37] octa(6- O -sulfo)-γ-cyclodextrin [41], lysine-bridged hemispherodextrin [42], methylated β-CD [43], mono-6-deoxy-6-(4-amino-1,2,4-triazolium)-β-CD chloride [44], mono-6-deoxy-6-(3-methylimidazolium)-β-CD tosylate [45], quaternary ammonium β-CD [46], carboxymethyl-β-CD [47,48], hydroxypropyl-γ-CDs [21,34], sulphated-γ-CDs [21] and highly sulphated-γ-CDs [49]. Sulfobutylether-β-CDs are also available commercially as Captisol ® and were applied successfully in the enantiomeric separation of neutral and basic drugs, but not towards negatively charged analytes in EKC [50].…”

Section: Macromoleculesmentioning

confidence: 99%

“…An IL-functionalised β-CD, mono-6-deoxy-(4-amino-1,2,4-triazolium)-β-CD chloride was prepared and successfully applied as CS for dansyl amino acids and naproxen [44]. Improved water solubility and additional non-bonding interactions from the IL functionalisation as shown in molecular dynamics calculations were perhaps the reasons behind improved resolution.…”

Section: Macromoleculesmentioning

confidence: 99%

“…Molecular modelling can help the researcher understand the different steps involved in the molecular recognition process, the non-bonding interactions involved between the analyte and the CS and the binding energies for their association. During this review period, ten studies utilised molecular modelling, with the intention of understanding chiral recognition mechanism and elution migration order [22,32,35,44,60,62,72,73,94,95]. Molecular modelling has also been utilised to design new CSs [40].…”

Section: Molecular Modelling and Nmr Studiesmentioning

confidence: 99%

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Chiral Selectors in Capillary Electrophoresis: Trends during 2017–2018

Quirino

2019

Molecules

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Chiral separation is an important process in the chemical and pharmaceutical industries. From the analytical chemistry perspective, chiral separation is required for assessing the fit-for-purpose and the safety of chemical products. Capillary electrophoresis, in the electrokinetic chromatography mode is an established analytical technique for chiral separations. A water-soluble chiral selector is typically used. This review therefore examines the use of various chiral selectors in electrokinetic chromatography during 2017–2018. The chiral selectors were both low and high (macromolecules) molecular mass molecules as well as molecular aggregates (supramolecules). There were 58 papers found by search in Scopus, indicating continuous and active activity in this research area. The macromolecules were sugar-, amino acid-, and nucleic acid-based polymers. The supramolecules were bile salt micelles. The low molecular mass selectors were mainly ionic liquids and complexes with a central ion. A majority of the papers were on the use or preparation of sugar-based macromolecules, e.g., native or derivatised cyclodextrins. Studies to explain chiral recognition of macromolecular and supramolecular chiral selectors were mainly done by molecular modelling and nuclear magnetic resonance spectroscopy. Demonstrations were predominantly on drug analysis for the separation of racemates.

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Synthesis and application of ionic liquid functionalized β-cyclodextrin, mono-6-deoxy-6-(4-amino-1,2,4-triazolium)-β-cyclodextrin chloride, as chiral selector in capillary electrophoresis

Cited by 50 publications

References 37 publications

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Native and substituted cyclodextrins as chiral selectors for capillary electrophoresis enantioseparations: Structures, features, application, and molecular modeling

Chiral Separations by Capillary Electrophoresis and related Techniques with Different Chiral Selectors: A Review

Chiral Selectors in Capillary Electrophoresis: Trends during 2017–2018

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