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A novel positively charged achiral co-monomer for ?-cyclodextrin monolithic stationary phase: improved chiral separation of acidic compounds using capillary electrochromatography coupled to mass spectrometry.

ABSTRACT: The work presented here demonstrates the incorporation of vinylbenzyl trimethylammonium (VBTA) as a novel positively charged achiral co-monomer to a glycidyl methacrylate-beta cyclodextrin (GMA/?-CD) based monolith, providing anion exchange sites with reversed electroosmotic flow (EOF) for capillary electrochromatography (CEC). The monolithic phases, GMA/?-CD-VBTA and GMA/?-CD (without co-monomer) were characterized by scanning electron microscopy, optical microscopy, pressure drop/flow-rate curves and nitrogen adsorption analysis. After optimizing the stationary phase and mobile phase parameters, chiral separations of 41 pairs of structurally diverse anionic chiral analytes were compared individually using the GMA/?-CD-VBTA and GMA/?-CD monolithic columns. The GMA/?-CD-VBTA monolith chiral stationary phase separated significantly more acidic compounds compared to the GMA/?-CD column. To-date there has been limited work in the development of chiral monolithic column for CEC-mass spectrometry (MS). Because of good electrodriven flow characteristics, which allow the column to maintain a stable current in the absence of outlet vial, GMA/?-CD-VBTA column was successfully coupled to single quadrupole mass spectrometer for CEC-MS of several chiral test compounds. In addition, the same monolithic CEC column when coupled to a triple quadrupole MS instrument, two orders of magnitude higher sensitivity was observed compared to a single quadrupole MS instrument.

SUBMITTER: Bragg W

PROVIDER: S-EPMC3618962 | biostudies-literature | 2012 Dec

REPOSITORIES: biostudies-literature

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A novel positively charged achiral co-monomer for β-cyclodextrin monolithic stationary phase: improved chiral separation of acidic compounds using capillary electrochromatography coupled to mass spectrometry.

Bragg William W Shamsi Shahab A SA

Journal of chromatography. A 20120819

The work presented here demonstrates the incorporation of vinylbenzyl trimethylammonium (VBTA) as a novel positively charged achiral co-monomer to a glycidyl methacrylate-beta cyclodextrin (GMA/β-CD) based monolith, providing anion exchange sites with reversed electroosmotic flow (EOF) for capillary electrochromatography (CEC). The monolithic phases, GMA/β-CD-VBTA and GMA/β-CD (without co-monomer) were characterized by scanning electron microscopy, optical microscopy, pressure drop/flow-rate cur ...[more]

PMID: 23062876

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Project description:The applications of polysaccharide phenyl carbamate derivatives as chiral stationary phases (CSPs) for capillary electrochromatography (CEC) are often hindered by longer retention times, especially using a normal-phase (NP) eluent due to very low electroosmotic flow (EOF). Therefore, in this study, we propose an approach for the aforementioned problems by introducing two new types of negatively charged sulfate and sulfonated groups for polysaccharide CSPs. These CSPs were utilized to pack CEC columns for enantioseparation with a NP eluent. Compared to conventional cellulose tris(3,5-dimethylphenyl carbamate) or CDMPC CSPs, the sulfated CDMPC CSP (sulfur content 4.25%, w/w) shortened the analysis time up to 50% but with a significant loss of enantiomeric resolution (approximately 60%). On the other hand, the sulfonated CDMPC CSP (sulfur content 1.76%, w/w) not only provided fast throughput but also maintained excellent resolving power. In addition, its synthesis is much more straightforward than the sulfated one. Furthermore, we studied several stationary phase parameters (CSP loading and silica gel pore size) and mobile phase parameters (including type of mobile phase and its composition) to evaluate the throughput and enantioselectivity. Using the optimized conditions, a chiral pool containing 66 analytes was screened to evaluate the enantioselectivity under three different mobile phase modes (i.e., NP, polar organic phase (POP) and reversed-phase (RP) eluents). Among these mobile phase modes, the RP mode showed the highest success rate, whereas some degree of complementary enantioselectivity was observed with NP and POP. Finally, the feasibility of applying this CSP for CEC-MS enantioseparation using internal tapered column was evaluated with NP, POP and RP eluents. In particular, the NP-CEC-MS provided significantly enhanced sensitivity when methanol was replaced with isopropanol in the sheath liquid. Using aminoglutethimide as model chiral analyte, all three modes of CEC-MS demonstrated excellent durability as well as excellent reproducibility of retention time and enantioselectivity.

Dataset Information

A novel positively charged achiral co-monomer for ?-cyclodextrin monolithic stationary phase: improved chiral separation of acidic compounds using capillary electrochromatography coupled to mass spectrometry.

Publications

A novel positively charged achiral co-monomer for β-cyclodextrin monolithic stationary phase: improved chiral separation of acidic compounds using capillary electrochromatography coupled to mass spectrometry.

Similar Datasets

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