Comparative Enantiomer-Resolving Ability of Coated and Covalently Immobilized Versions of Two Polysaccharide-Based Chiral Selectors in High-Performance Liquid Chromatography

A novel high‐performance liquid chromatography (HPLC) multifunctional immobilized chiral stationary phase was prepared by bonding dialdehyde microcrystalline cellulose to aminosilica via Schiff base reaction and then derivatized with 3,5‐dimethylphenyl isocyanate. The HPLC multifunctional immobilized chiral stationary phase could not only achieve chiral separation but also achieve achiral separation. Chiral separation evaluation showed that 1‐(1‐naphthyl)ethanol and mandelonitrile got separation in normal phase (NP) mode. Ranolazine, benzoin ethyl ether, metalaxyl, and diclofop were successfully separated in reversed phase (RP) mode. Aromatic compounds such as polycyclic aromatic hydrocarbons (PAHs), anilines, and aromatic acids were selected as analytes to investigate the achiral separation performance of the multifunctional immobilized chiral stationary phase in NP and RP modes. The achiral separation evaluation showed that six PAHs could get good separation within 10 minutes in NP mode. Four aromatic acids were well separated in RP mode. The retention mechanism of aromatic compounds on the stationary phase was discussed, founding that π‐π interaction, π‐π electron‐donor‐acceptor (EDA) interaction, and hydrogen bonding interaction played important roles during the achiral separation process. This multifunctional immobilized chiral stationary phase had the advantages of simple bonding steps, short reaction time, and no need for space arm.

Section: Resultsmentioning

confidence: 99%

Section: Solvent Resistance Of Dmcdmpc/sio 2 Columnmentioning

confidence: 99%

Preparation and chromatographic performance of a multifunctional immobilized chiral stationary phase based on dialdehyde microcrystalline cellulose derivatives

Gao

Chen

et al. 2019

“…However, polysaccharide‐coated CSPs could not be applied in RP and polar solvent conditions because polar solvents could dissolve and swell polysaccharide derivatives. In response to this problem, a series of immobilized CSPs have been developed …”

Section: Resultsmentioning

confidence: 99%

Preparation and evaluation of biselector bonded‐type multifunctional chiral stationary phase based on dialdehyde cellulose and 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine derivatives

Gao

Quan

et al. 2020

A novel biselector bonded‐type multifunctional chiral stationary phase (MCSP) was prepared by covalently crosslinking dialdehyde cellulose (DAC) with 6‐monodeoxy‐6‐monoamino‐β‐cyclodextrine (CD) via Schiff base reaction. The biselector bonded‐type MCSP had good chiral and achiral chromatographic performance in normal phase (NP) and reversed phase (RP) modes. Seven and eight enantiomers were successfully separated on the prepared biselector bonded‐type MCSP in NP and RP modes, respectively. The biselector bonded‐type MCSP showed enhanced chiral resolution ability compared with single selector chiral stationary phases due to the simultaneous introduction of DAC and 6‐monodeoxy‐6‐monoamino‐β‐CD on the surface of silica gel. Aromatic compounds including polycyclic aromatic hydrocarbons, anilines, phenols, phenylates, and aromatic acids were choosed as analytes to investigate the achiral chromatographic performance of the biselector bonded‐type MCSP in NP and RP modes. Chromatographic evaluation results showed that the above aromatic compounds were essentially capable of achieving baseline separation by hydrophobic interaction, π‐π interaction, and π‐π electron‐donor‐acceptor interaction. Moreover, the host‐guest inclusion effect of 6‐monodeoxy‐6‐monoamino‐β‐CD and the multiple interactions made the biselector bonded‐type MCSP have good steric selectivity. The preparation method of the biselector bonded‐type MCSP was simple and provided a new idea and strategy for the preparation of the subsequent novel biselector MCSP.

“…The selection of chiral column with different stationary phases is a key factor to achieve efficient enantioseparation. Among the various CSPs, the polysaccharide‐based CSPs are extensively used, which show good chiral recognition ability toward many chiral compounds …”

Section: Resultsmentioning

confidence: 99%

“…Among the various CSPs, the polysaccharide-based CSPs are extensively used, which show good chiral recognition ability toward many chiral compounds. [26][27][28][29][30] In the preliminary experiments, the enantioseparation of flumequine on four cellulose-based columns (Chiralpak IB and Chiralpak IC, Chiralcel OD-RH and Chiralcel OJ-RH) and two amylose-based chiral columns (Chiralpak IA and Chiralpak ID) was tested using a variety of reversed-phase mobile phase combinations. The initial column screening was conducted under the same mobile condition, with a organic solvent of 80% methanol or 60% acetonitrile at a flow rate of 0.6 mL min -1 .…”

Section: Effect Of Cspsmentioning

confidence: 99%

Enantioseparation and determination of flumequine enantiomers in multiple food matrices with chiral liquid chromatography coupled with tandem mass spectrometry

Liu

Xue

et al. 2019

The present work firstly described the enantioseparation and determination of flumequine enantiomers in milk, yogurt, chicken, beef, egg, and honey samples by chiral liquid chromatography‐tandem mass spectrometry. The enantioseparation was performed under reversed‐phase conditions on a Chiralpak IC column at 20°C. The effects of chiral stationary phase, mobile phase components, and column temperature on the separation of flumequine enantiomers have been studied in detail. Target compounds were extracted from six different matrices with individual extraction procedure followed by cleanup using Cleanert C18 solid phase extraction cartridge. Good linearity (R2>0.9913) was obtained over the concentration range of 0.125 to 12.5 ng g‐1 for each enantiomer in matrix‐matched standard calibration curves. The limits of detection and limits of quantification of two flumequine enantiomers were 0.015‐0.024 and 0.045‐0.063 ng g‐1, respectively. The average recoveries of the targeted compounds varied from 82.3 to 110.5%, with relative standard deviation less than 11.7%. The method was successfully applied to the determination of flumequine enantiomers in multiple food matrices, providing a reliable method for evaluating the potential risk in animal productions.