Enantiomeric Separation of Chiral Triazole Pesticides by a <i>mono</i>-6-(4-Nitrophenyl)-ureido-β-cyclodextrin-Bonded Stationary Phase Using High-Performance Liquid Chromatography

Shuang, Yazhou; Cao, Zhigang; Zhang, Tianci; Li, Laisheng

doi:10.1080/00032719.2020.1745821

Cited by 9 publications

(6 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…CD-containing chiral stationary phase (CSP) is extensively used in gas chromatography (GC), high-performance liquid chromatography (HPLC), thin-layer chromatography (TLC), micro solid phase extraction (μ-SPE), capillary electrophoresis (CE), capillary electrochromatography (CEC), electrokinetic chromatography (EKC), and supercritical fluid chromatography (SFC) for the separation of structurally similar compounds or complex product matrices of enantiomers [ 96 , 97 , 98 , 99 , 100 , 101 ]. The derivatization or coupling of CDs using various functional molecules is also widely employed in this field [ 102 , 103 , 104 , 105 , 106 , 107 , 108 , 109 , 110 , 111 , 112 ]. One such example can be seen in the study conducted by Sun et al, in which per-4-chlorophenylcarbamate/β-cyclodextrin-based CSP was developed and successfully applied for the separation of flurbiprofen enantiomers and 22 other drug racemates [ 109 , 110 ].…”

Section: Applications Of CD Inclusion Complexes In the Solid/solutmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

View full text Add to dashboard Cite

Cyclodextrins (CDs) have drawn a lot of attention from the scientific communities as a model system for host–guest chemistry and also due to its variety of applications in the pharmaceutical, cosmetic, food, textile, separation science, and essential oil industries. The formation of the inclusion complexes enables these applications in the condensed phases, which have been confirmed by nuclear magnetic resonance (NMR) spectroscopy, X-ray crystallography, and other methodologies. The advent of soft ionization techniques that can transfer the solution-phase noncovalent complexes to the gas phase has allowed for extensive examination of these complexes and provides valuable insight into the principles governing the formation of gaseous noncovalent complexes. As for the CDs’ host–guest chemistry in the gas phase, there has been a controversial issue as to whether noncovalent complexes are inclusion conformers reflecting the solution-phase structure of the complex or not. In this review, the basic principles governing CD’s host–guest complex formation will be described. Applications and structures of CDs in the condensed phases will also be presented. More importantly, the experimental and theoretical evidence supporting the two opposing views for the CD–guest structures in the gas phase will be intensively reviewed. These include data obtained via mass spectrometry, ion mobility measurements, infrared multiphoton dissociation (IRMPD) spectroscopy, and density functional theory (DFT) calculations.

show abstract

Section: Applications Of CD Inclusion Complexes In the Solid/solutmentioning

confidence: 99%

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Lee

2020

Molecules

View full text Add to dashboard Cite

show abstract

“…Shuang et al [ 58 ] also developed a new β-cyclodextrin-bonded CSP based on a mono -6-amino-β-cyclodextrin immobilized onto ordered mesoporous silica gel ( Figure 5 B) using 3-(triethoxysilyl)propyl isocyanate. The introduction of an ureido moiety allowed the possibility to have a group with a hydrogen-bond accepting and donating properties.…”

Section: Immobilization Methodsmentioning

confidence: 99%

“…The new CSP demonstrated a superior enantioselectivity in comparison with native β-cyclodextrin CSP. Besides NMR, SEM, TEM, X-ray diffraction, N 2 adsorptio–desorption isotherm, elemental analysis and TGA were applied on CSP characterization [ 58 ].…”

Section: Immobilization Methodsmentioning

confidence: 99%

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

et al. 2021

View full text Add to dashboard Cite

Enantioselective chromatography is one of the most used techniques for the separation and purification of enantiomers. The most important issue for a specific successful enantioseparation is the selection of the suitable chiral stationary phase (CSP). Different synthetic approaches have been applied for the preparation of CSPs, which embrace coating and immobilization methods. In addition to the classical and broadly applied coating and immobilization procedures, innovating strategies have been introduced recently. In this review, an overview of different methods for the preparation of coated and immobilized CSPs is described. Updated examples of CSPs associated with the various strategies are presented. Considering that after the preparation of a CSP its characterization is fundamental, the methods used for the characterization of all the described CSPs are emphasized.

show abstract

“…Since the piperidine group contained neither π electrons nor a chiral center, the mono-6-deoxy-6-(piperidine)-β-CD-based CSP gave the poorest chiral resolution. In addition, several mono-substituted CD-based CSPs have been reported by Li and co-workers in recent years [56][57][58]. In 2019, Li and co-workers synthesized a benzylureido-mono-derivatizedβ-CD and bonded it onto silica by a "thiol-ene" click reaction to prepare a CSP for HPLC resolution of enantiomers of phenylmercapturic and benzylmercapturic acid biomarkers [56].…”

Section: Mono-substituted CD Derivative-based Cspsmentioning

confidence: 99%

“…In 2019, Li and co-workers synthesized a benzylureido-mono-derivatizedβ-CD and bonded it onto silica by a "thiol-ene" click reaction to prepare a CSP for HPLC resolution of enantiomers of phenylmercapturic and benzylmercapturic acid biomarkers [56]. More recently, a mono-6-(4-nitrophenyl)ureido-β-CD-based CSP which contained one π-electronwithdrawing group (4-nitrophenyl) at the C-6 position of CD was prepared by the same group [57]. Many triazole chiral pesticides with π-electron-rich (π-basic) moieties were efficiently resolved on the CSP due to the presence of the π-electron-accepting (π-acidic) nitrophenyl group.…”

Section: Mono-substituted CD Derivative-based Cspsmentioning

confidence: 99%

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Zhang

2021

J of Separation Science

View full text Add to dashboard Cite

Separations and analyses of chiral compounds are important in many fields, including pharmaceutical production, preparation of chemical intermediates, and biochemistry. High-performance liquid chromatography using a chiral stationary phase is regarded as one of the most valuable methods for enantiomeric separation and analysis because it is highly efficient, is broadly applicable, and has powerful separation capability. The focus for development of this method is the identification of novel chiral stationary phases with superior recognition performance and good stability. The present article reviews recent progress in the development of new chiral stationary phases for high-performance liquid chromatography between January 2018 and June 2021. These newly reported chiral stationary phases are divided into three categories: small organic moleculebased (cyclodextrin and its derivatives, macrocyclic antibiotics, cinchona alkaloids, and other low molecular weight chiral molecules), macromoleculebased (cellulose and amylose derivatives, chitin and chitosan derivatives, and synthetic helical polymers) and chiral porous material-based (chiral metal-organic frameworks, chiral covalent organic frameworks, and chiral inorganic mesoporous silicas). Each type of chiral stationary phase is discussed in detail.

show abstract

Enantiomeric Separation of Chiral Triazole Pesticides by a mono-6-(4-Nitrophenyl)-ureido-β-cyclodextrin-Bonded Stationary Phase Using High-Performance Liquid Chromatography

Cited by 9 publications

References 36 publications

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Noncovalent Complexes of Cyclodextrin with Small Organic Molecules: Applications and Insights into Host–Guest Interactions in the Gas Phase and Condensed Phase

Strategies for Preparation of Chiral Stationary Phases: Progress on Coating and Immobilization Methods

Recent progress in the development of chiral stationary phases for high‐performance liquid chromatography

Contact Info

Product

Resources

About