Enantioseparation of N-derivatized amino acids by micro-liquid chromatography using carbamoylated quinidine functionalized monolithic stationary phase

Wang, Qiqin; Feng, Jun; Han, Hai; Zhu, Ping; Wu, Huihui; Marina, Marı́a Luisa; Crommen, Jacques; Jiang, Zhengjin

doi:10.1016/j.chroma.2014.06.039

Cited by 33 publications

(15 citation statements)

References 38 publications

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“…Cyclohexanol, tropic acid, 2‐phenoxypropionic acid, 2‐phenylpropionic acid, 4‐methoxymandelic acid, 3,4‐difluoromandelic acid, 2‐bromo‐2‐phenylacetic acid, 2‐phenylbutyric acid, chlortalidone, and 4‐hydroxymandelic acid monohydrate were obtained from Energy Chemical (Shanghai, China). N ‐Benzoylleucine, 2‐chloro‐benzoyl leucine, and 3,5‐DNB‐phenylalanine were synthesized in our laboratory . Deionized water was filtered through 2 μm membrane before use.…”

Section: Methodsmentioning

confidence: 99%

Effect of fabrication strategy on the enantioseparation performance of β‐cyclodextrin‐functionalized polymethacrylate monoliths: A comparative evaluation

Yang

Guo

Lin

et al. 2017

J of Separation Science

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To evaluate the effect of the preparation strategy on the enantioseparation performance of β-cyclodextrin-functionalized monoliths, a series of β-cyclodextrin-functionalized organic polymeric monolithic columns were prepared through two-step, single-step, and one-pot approaches, using the same cyclodextrin, linker-spacer, and crosslinker. Physicochemical characterization of the columns was carried out by determining the morphology, β-cyclodextrin density, permeability, and chromatographic efficiency. For each type of monolithic column, the enantioresolution of 22 chiral compounds, including mandelic acid derivatives, nonsteroidal anti-inflammatory drugs, N-derivatized amino acids, and herbicides, was comparatively studied under optimum chromatographic conditions. The β-cyclodextrin-functionalized monolithic columns prepared through the one-pot approach exhibited higher enantioresolution for most chiral compounds, and they have the advantage of good controllability and simple preparation. On the other hand, the enantioresolution obtained on columns prepared through the single-step approach was quite unsatisfactory, and therefore the effect of using different linking spacers and crosslinkers was studied. A significant improvement of enantioresolution for 2-chloro-mandelic acid was obtained by using N,N-methylenebisacrylamide instead of ethylene dimethacrylate as the crosslinker in the single-step preparation.

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Section: Methodsmentioning

confidence: 99%

Effect of fabrication strategy on the enantioseparation performance of β‐cyclodextrin‐functionalized polymethacrylate monoliths: A comparative evaluation

Yang

Guo

Lin

et al. 2017

J of Separation Science

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“…). Briefly, the fused‐silica capillaries were pretreated with γ ‐MAPS prior to polymerization . The polymerization mixture containing the functional monomer (NA‐D‐ tert ‐Leu‐MA), the crosslinker (EDMA), the initiator AIBN (1 wt% with respect to the monomers) and the porogens (MeOH and THF) was mixed ultrasonically into a homogeneous solution in a 3 mL vial.…”

Section: Methodsmentioning

confidence: 99%

Preparation and evaluation of tert‐leucine derivative functionalized polymeric monoliths for micro‐liquid chromatography

Ruan

Wang

et al. 2017

Electrophoresis

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In this study, a novel functional monomer N-[1-(α-naphthyl)ethylaminocarbonyl]-D-tert-leucine-[2-(methacryloyloxy)ethyl] amide (NA-D-tert-Leu-MA) was synthesized, and then employed to prepare polymeric monoliths (240 mm × 100 μm id) functionalized with tert-leucine derivative through a single step thermo-initiated co-polymerization approach or a multi-step post-modification approach. The multi-step approach involves the post-modification of a thiol-containing monolith with NA-D-tert-Leu-MA via "thiol-ene"click reaction. The physicochemical properties of the resulting monoliths were characterized by scanning electron microscopy, energy-dispersive X-ray spectrometry and micro-liquid chromatography. Good column stability, permeability, efficiency and reproducibility were obtained for the optimized monoliths. The poly (NA-D-tert-Leu-MA-co-ethylene dimethacrylate) monolith prepared through the single step co-polymerization approach exhibited satisfactory achiral separation performance for various analytes, including phenols, aniline derivatives and intact proteins, while its enantioseparation ability is rather poor. In contrast to that, the monolith prepared through the multi-step post-modification approach showed much higher enantioselectivity for 7-nitro-2,1,3-benzoxadiazole (NBD)-derivatized amino acids. Three NBD-derivatized amino acids (theanine, proline and norleucine) could be baseline enantioseparated.

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“…The influence of organic solvents composition, buffer concentration, and the apparent pH of the mobile phase on the enantioseparation and retention seems to confirm that both hydrophobic and electrostatic interactions are responsible for the retention of these acidic analytes. The prepared monolithic column after optimization was finally applied to the enantioseparation of a wide range of N ‐derivatized amino acids with good resolution and high selectivity especially for 3,5‐dinitrobenzoyl‐amino acids (DNB‐AA) and 3,5‐dichlorobenzoyl‐amino acids (DClB‐AA) (Figure ) .…”

Section: Monolithic Stationary Phasesmentioning

confidence: 99%

An insight into chiral monolithic stationary phases for enantioselective high‐performance liquid chromatography applications

Fouad

Ibrahim

Adly

et al. 2019

J of Separation Science

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In this review, three main classes of chiral monolithic stationary phases, namely silica-, organic polymer-, and hybrid-based monolithic stationary phases, are covered. Their preparations, applications, and advantages compared with the conventionalpacked and open-tubular capillary columns are discussed. A detailed description of the different types and techniques used for the introduction of chiral selectors into the monolithic matrices such as immobilization, functionalization, coating, encapsulation, and bonding. Special emphasis is given to the recent developments of chiral selectors in HPLC monolithic stationary phases during the past 18 years.

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Enantioseparation of N-derivatized amino acids by micro-liquid chromatography using carbamoylated quinidine functionalized monolithic stationary phase

Cited by 33 publications

References 38 publications

Effect of fabrication strategy on the enantioseparation performance of β‐cyclodextrin‐functionalized polymethacrylate monoliths: A comparative evaluation

Effect of fabrication strategy on the enantioseparation performance of β‐cyclodextrin‐functionalized polymethacrylate monoliths: A comparative evaluation

Preparation and evaluation of tert‐leucine derivative functionalized polymeric monoliths for micro‐liquid chromatography

An insight into chiral monolithic stationary phases for enantioselective high‐performance liquid chromatography applications

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