Polar silica-based stationary phases. Part II- Neutral silica stationary phases with surface bound maltose and sorbitol for hydrophilic interaction liquid chromatography

Rathnasekara, Renuka; Rassi, Ziad El

doi:10.1016/j.chroma.2017.05.059

Cited by 13 publications

(7 citation statements)

References 27 publications

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“…The compound 3 was synthesized with the reaction of (R)-2-amino-1-butanol (2) and N-p-nitrobenzyl bromide (1) in the presence sodium carbonate in benzene with dean stark apparatus for 12 h. The structures of compounds were explained on the basis of spectral data (NMR).…”

Section: Chemistrymentioning

confidence: 99%

“…Therefore, the separation of racemates is required for applications in many different areas such as the pharmaceutical industry, environmental chemistry, food chemistry and agriculture. [1][2][3][4][5][6] In the chiral resolution of a racemic mixtures in chemistry, the various methods such as asymmetric synthesis, chromatographic separation, chemical or enzymatic kinetic resolution, and diastereomeric crystallization were utilized to acquire selectively the desired enantiomer. Among the methods used for the chiral resolution, enantio separation by HPLC using CSPs is currently the most popular one.…”

Section: Introductionmentioning

confidence: 99%

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Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

Çakmak¹,

Ercan²,

Sünkür³

et al. 2017

Org. Commun.

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This study consists of two parts. In the first part of the study; a Pirkle-type chiral stationary phase was prepared by synthesizing an aromatic amine derivative of (R)-2-amino-1-butanol as a chiral selector and binding to L-tyrosine-modified cyanogen bromide (CNBr)-activated Sepharose 4B and then, packed into the separation column. The chromatographic performance of the separation column was evaluated with racemic mandelic acid and 2-phenylpropionic acid by using phosphate buffers at three different pHs as mobile phase. In the resolution processes, the prepared solutions were loaded onto the separation column at two different concentrations and at three different pHs for each racemic organic acid, separately. Enantiomeric excess (ee%) of the eluates was determined on CHIRALPAK AD-H chiral analytical column by HPLC. The maximum ee% for mandelic acid and 2-phenylpropionic acid was determined to be 60.84 and 27.4, respectively. Separation factors (k 1 ' , k 2 ' , α, and Rs) were calculated for each acid. The structures of the obtained compounds were characterized using the spectroscopic methods (NMR, and elemental analysis). In the second part of the study; enantioselective interactions between the prepared CSP and the analytes have been widely studied by docking, molecular dynamics simulation and quantum mechanical computation methods. The reason of column eluation of rac-2-phenylpropionic acid with lower enantiomeric yield was explained by these techniques.

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Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

Çakmak¹,

Ercan²,

Sünkür³

et al. 2017

Org. Commun.

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“…Hydrophilic interaction liquid chromatography (HILIC) is increasingly used for the separation of neutral and charged polar and slightly polar substances on polar stationary phases (i.e., a highly hydrated sorbent). In principle, it exhibits a different selectivity when compared to the traditional reversed-phase chromatography (RPC) and permits the separation of highly polar analytes that are basically un-retained under RPC conditions [1][2][3][4]. Unique selectivity and high separation efficiency are attained in HILIC using polar adsorbents with different structures and nature of functional groups.…”

Section: Introductionmentioning

confidence: 99%

“…Unique selectivity and high separation efficiency are attained in HILIC using polar adsorbents with different structures and nature of functional groups. Stationary phases with amide and hydroxyl functionalities establish the strongest hydrophilicity and retention factors for polar analytes [1,2]. However, novel stationary phases with enhanced efficiency and alternative selectivity are still one of the major directions in the development of the HILIC mode [5,6].…”

Section: Introductionmentioning

confidence: 99%

Silica-Based Stationary Phase with Surface Bound N-Acetyl-glucosamine for Hydrophilic Interaction Liquid Chromatography

Rajendiran,

El Rassi

2023

Molecules

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A hydrophilic silica-based stationary phase with surface bound N-acetylglucosamine (GlcNAc-silica) was prepared in house and characterized physically via Fourier transform infrared (FTIR) analysis and thermogravimetric analysis (TGA) and chromatographically over a wide range of mobile phase compositions. While both FTIR and TGA confirmed the attachment of the GlcNAc ligands to the silica surface, the chromatographic evaluation of GlcNAc-silica with polar and slightly polar standard solutes (e.g., sugars, nucleic acid fragments, phenolic, and benzoic acid derivatives) yielded the typical hydrophilic interaction liquid chromatography (HILIC) behaviors in the sense that retention increased with increases in solute polarity and the organic content (i.e., acetonitrile) of the hydro-organic mobile phase (i.e., ACN-rich mobile phase). Sugars derivatized with 1-naphthylamine (1-NA) and 2-aminoanthrcene (2-AA) such as xylose, glucose, and short chains maltooligosaccharides constituted the most polar species for HILIC retention evaluation, and in addition, the maltooligosaccharides offered a polar homologous series for gauging the hydrophilicity of GlcNAc-silica in analogy with alkylbenzene homologous series and other nonpolar homologues for evaluating the hydrophobicity of non-polar stationary phases. On the other hand, the benzoic acid and phenolic acid derivatives were the probe solutes for evaluating the HILIC retention dependence of ionizable solutes on the pH of the mobile phase. Similarly, the nucleobase and nucleoside weak basic solutes as well as some typical cyclic nucleotide acidic solutes allowed for the examination of the dependence of solute retention on the pH of the mobile as well as the polarity of the species.

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“…HILC, one chromatographic mode with good separation ability of strongly polar compounds, was first proposed in 1990 [11]. The binding of monosaccharides [12], maltose, isosorbide [13], and oligosaccharides [14] on the surface of silica gel has also been reported. However, these natural sugar structures are only suitable for analysis in specific fields.…”

Section: Introductionmentioning

confidence: 99%

Glycopolymer Grafted Silica Gel as Chromatographic Packing Materials

Luo

Sun

et al. 2018

IJMS

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The modification of the surface of silica gel to prepare hydrophilic chromatographic fillers has recently become a research interest. Most researchers have grafted natural sugar-containing polymers onto chromatographic surfaces. The disadvantage of this approach is that the packing structure is singular and the application scope is limited. In this paper, we explore the innovative technique of grafting a sugar-containing polymer, 2-gluconamidoethyl methacrylamide (GAEMA), onto the surface of silica gel by atom transfer radical polymerization (ATRP). The SiO2-g-GAEMA with ATRP reaction time was characterized by Fourier infrared analysis, Thermogravimetric analysis (TGA), and elemental analysis. As the reaction time lengthened, the amount of GAEMA grafted on the surface of the silica gel gradually increased. The GAEMA is rich in amide bonds and hydroxyl groups and is a typical hydrophilic chromatography filler. Finally, SiO2-g-GAEMA (reaction time = 24 h) was chosen as the stationary phase of the chromatographic packing and evaluated with four polar compounds (uracil, cytosine, guanosine, and cytidine). Compared with unmodified silica gel, modified silica gel produces sharper peaks and better separation efficiency. This novel packing material may have a potential for application with highly isomerized sugar mixtures.

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Polar silica-based stationary phases. Part II- Neutral silica stationary phases with surface bound maltose and sorbitol for hydrophilic interaction liquid chromatography

Cited by 13 publications

References 27 publications

Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

Design, preparation and application of a Pirkle-type chiral stationary phase for enantioseparation of some racemic organic acids and molecular dynamics studies

Silica-Based Stationary Phase with Surface Bound N-Acetyl-glucosamine for Hydrophilic Interaction Liquid Chromatography

Glycopolymer Grafted Silica Gel as Chromatographic Packing Materials

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