Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC

Yi, Jingxuan; Xu, Lu; Wang, Hui; Yin, Xiaoxing; Zhou, Xueyan; Yin, Jie; Wang, Yinan; Hou, Jasmine; Wei, Qi; Gong, Yiwei

doi:10.1007/s10337-020-03908-w

Cited by 8 publications

(5 citation statements)

References 27 publications

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“…A new cyclodextrin-based CSP was reported by Yi et al [ 60 ] by using phenyl isocyanate to obtain the partially substituted phenylcarbamate-(3-(2- O -β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-appended silica particles ( Figure 5 D). The CSP demonstrated enantioselectivity for different positional isomers (nitrophenol and nitroaniline) and enantiomers of chiral drugs being operated in multi-mode LC mobile phase conditions.…”

Section: Immobilization Methodsmentioning

confidence: 99%

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

et al. 2021

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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.

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Section: Immobilization Methodsmentioning

confidence: 99%

“…An improved enantioselectivity was obtained in comparison with commercial columns Cyclobond I DMP ® and Cyclobond I SN ® . An elemental analysis and FTIR were applied for the characterization of this new CSP [ 60 ].…”

Section: Immobilization Methodsmentioning

confidence: 99%

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

et al. 2021

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“…3. (13)(14)(15)(16)(17)(18)(19)(20)(21) the eluent was modi ed with 0.1% DEA, for amphoteric compounds (22)(23)(24)(25) the eluent was modi ed with the mixture of DEA-acetic acid 0.1%-0.1% (v/v).…”

Section: Screening In Polar Organic Modementioning

confidence: 99%

“…One of the key advantages of using CD-based CSPs in chiral separations is the ability to utilize multimodal elution, which enables the resolution of a wide range of stereoisomeric compounds through the combination of different elution modes, including reversed-phase, normal-phase, and polar organicmode [20]. Several studies recommend using reversed-phase or normal-phase mode with CD-based CSPs [21,22].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation and modeling study of selected chiral pharmaceuticals on a commercialized phenylcarbamate-β-cyclodextrin column using polar organic mode

Dobó

Ádám

Fiser

et al. 2023

Preprint

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The chiral separation capability of Chiral-CD-Ph column, containing phenylcarbamate-β-cyclodextrin as the chiral selector in polar organic mode was investigated. A total of 25 compounds with different structures and acid-base properties were tested, and 20 of them were separated using acetonitrile or methanol as eluent. The effects of various chromatographic parameters, such as the type and proportion of organic modifier, flow rate, and column temperature were analyzed in detail in relation to chromatographic performance. A U-shape retention curve was observed when a mixture of acetonitrile and methanol was used as the eluent, indicating different types of interactions in different solvent mixtures. Van 't Hoff analysis was used for calculation of thermodynamic parameters which revealed that the enantioseparation is mainly enthalpy controlled; however, entropic control was also observed. The enantiomer recognition ability at the atomic level was also investigated through a molecular modeling study, which revealed surface binding in polar organic mode instead of inclusion complexation. Our work proves that the phenylcarbamate-β-cyclodextrin chiral selector can be effectively used in polar organic mode for the chiral separation of compounds with diverse structures. Furthermore, it is also important to note that it was demonstrated that surface binding is responsible for the formation of supramolecular complexes in certain cyclodextrin derivatives.

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“…In addition to the partially substituted CD derivatives, fully derivatized CD derivatives, in which all of the hydroxyl groups at the C-2, C-3, and C-6 positions are functionalized, also have been widely used as CSPs for HPLC separation of enantiomers. Recently, a series of fully phenylcarbamoylated CD derivatives have been bonded onto silica gel to prepare CSPs for HPLC via various reactions and spacers [61][62][63][64][65][66][67][68]. Most of the studies focused on the introduction of different substituents to the benzene rings because the introduction of either electron-withdrawing or electron-donating substituents on the phenyl ring of phenylcarbamoylated CD CSPs generally improves enantioselectivity toward some racemates [69][70][71].…”

Section: Multi-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

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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.

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Preparation and Application of Partially Substituted Phenylcarbamate-(3-(2-O-β-cyclodextrin)-2-hydroxypropoxy)-propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode HPLC

Cited by 8 publications

References 27 publications

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

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

Enantioseparation and modeling study of selected chiral pharmaceuticals on a commercialized phenylcarbamate-β-cyclodextrin column using polar organic mode

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

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