Capillary electrochromatographic separation of enantiomers on chemically bonded type of cellulose derivative chiral stationary phases with a positively charged spacer

Chen, Xiaoming; Jin, Wenhai; Qin, Feng; Liu, Yueqi; Zou, Hanfa; Guo, Baochuan

doi:10.1002/elps.200305484

Cited by 34 publications

(30 citation statements)

References 24 publications

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“…The other limiting problem of efficiently coated polysaccharide CSPs is normally a relatively low EOF activity, especially at low pH, due to densely covered residual silanols that are the source for EOF generation. To overcome this drawback, Zou and co-workers [49] pursued a distinct strategy of immobilisation incorporating EOF active amino moieties into the linker. Hence, in 2003, they immobilized cellulose 2,3-bis(phenylcarbamate) and cellulose 2,3-bis(3,5-dimethylphenylcarbamate) onto 5 mm diethylenetriaminopropylated silica (DEAPS) using 2,4-diisocyanato-1-methylbenzene as bifunctional reagent for the regioselective immobilization at the free hydroxyl group at C 6 (Fig.…”

Section: Particle-packed Stationary Phasesmentioning

confidence: 99%

“…In order to study the influence of the additional supportive secondary amino groups present at the surface of the DEAPS phase similar CSPs were fabricated for the sake of comparison by immobilization of the cellulose derivatives onto 3-aminopropylated silica (APS) (Fig. 5) [49]. Employing acidic nonaqueous mobile phases under which the CSPs were positively charged the EOF (which was anodic) was up to 60% higher on the DEAPS-based column compared to the APS-based phase.…”

Section: Particle-packed Stationary Phasesmentioning

confidence: 99%

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Recent accomplishments in the field of enantiomer separation by CEC

Preinerstorfer

Lämmerhofer

2007

Electrophoresis

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Recent accomplishments in the field of enantiomer separation by CECThe present review intends to summarize recent developments in the field of enantioselective separations and analysis by CEC. It covers studies published in English language in common peer-reviewed journals within the period between 2003 and 2006. Both, methods making use of chiral mobile phase additives as well as chiral stationary phases for electrochromatographic enantiomer separations, are reviewed. Achievements that have been made on the various column technologies, such as open-tubular, particle-packed, inorganic, organic and particle-fixed (hybrid-type) monolithic as well as molecularly imprinted polymer phases, are discussed.

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Section: Particle-packed Stationary Phasesmentioning

confidence: 99%

Section: Particle-packed Stationary Phasesmentioning

confidence: 99%

Recent accomplishments in the field of enantiomer separation by CEC

Preinerstorfer

Lämmerhofer

2007

Electrophoresis

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“…[32][33][34][35][36] In addition to HPLC, the obtained CSPs have been applied to nano-liquid chromatography and capillary electrochromatography. 35,36 However, these CSPs …”

Section: Immobilization Of Polysaccharide Derivatives Using Diisocyanatementioning

confidence: 99%

Immobilized Polysaccharide-Based Chiral Stationary Phases for HPLC

Ikai

Yamamoto

Kamigaito

et al. 2006

Polym J

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ABSTRACT:Polysaccharide derivatives, such as phenylcarbamates and benzoates of cellulose and amylose, are known to show high chiral recognition abilities for many racemates when used as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC). This type of CSPs has usually been prepared by coating the polysaccharide derivatives onto a macroporous silica gel without a chemical bond. Therefore, rather limited numbers of solvents can be used as eluents, and solvents, such as chloroform and tetrahydrofuran (THF), which swell or dissolve the polysaccharide derivatives cannot be used. The selection of a suitable eluent is very important for both analytical and preparative separations. In order to enhance the versatility of the polysaccharide derivative-based CSPs, the derivatives have to be immobilized. Here we review the immobilization methods of the polysaccharide derivatives mainly onto silica gel. [DOI 10.1295/polymj.38.91] KEY WORDS Immobilization / Polysaccharide / Resolution / High Performance Liquid Chromatography / HPLC / Chiral Stationary Phase / CSP / Optically active compounds have been attracting much attention in many fields of science, and the demand for single enantiomers in the pharmaceutical industry has also been increasing. However, the separation or resolution of enantiomers is often laborious because most physical and chemical properties of enantiomers are identical. In the early 1970s, the first baseline separation of enantiomers by liquid chromatography was reported by Davankov, 1 and in 1981, the chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) developed by Pirkle 2 were for the first time commercialized. In the 1980s, the instrumentation for HPLC had remarkably advanced, and many efficient CSPs for HPLC had also been developed. [3][4][5][6][7][8][9] Today, most chiral compounds appear to be resolved by HPLC using CSPs. 10 The CSPs have been prepared with optically active small molecules 6,8,11 or polymers, [3][4][5][6][7][12][13][14][15] which are usually supported on silica gel. Among a large number of CSPs so far developed, phenylcarbamates of cellulose and amylose (Figure 1) exhibit broad applicability to a wide range of compounds. 10,[16][17][18][19][20][21] Some of the polysaccharide-based CSPs for HPLC have been commercially available. However, these polysaccharidebased CSPs can be used with a limited number of solvents, because some organic solvents, such as THF, chloroform, toluene, ethyl acetate, and acetone, dissolve or swell the polysaccharide derivatives and destroy their packed columns. Due to this solubility of the polysaccharide derivatives, the coated CSPs have usually been used with eluents consisting of alkanes/ alcohols mixtures or aqueous solvents containing alcohols or acetonitrile. These limitations in the mobile phase selection are sometimes a serious problem for efficient analytical and preparative resolution of enantiomers. 10,22 For a large scale preparative separation, good solubility of the sample is essen...

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“…Chen et al [48] prepared positively charged CSPs by chemically immobilizing cellulose derivatives onto diethylenetriaminopropylated silica (DEAPS) with tolylene-2, 4-diisocyanate (TDI) as a spacer reagent. The anodic electroosmotic mobility was observed in both nonaqueous and aqueous mobile phases due to the presence of positively charged amines on the surface of the prepared CSPs.…”

Section: Chemically Bonded Types Of Chiral Stationary Phases With Celmentioning

confidence: 99%

Polar stationary phases for capillary electrochromatography

Xie

et al. 2004

Electrophoresis

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This review article summarizes the variety of polar stationary phases that have been employed for capillary electrochromatographic separations. Compared with reversedphase stationary phases, the polar alternatives provide a completely different retention selectivity towards polar and charged analytes. Different types of polar stationary phases are reviewed, including the possible retention mechanisms. Electrochromatographic separations of polar solutes, peptides, and basic pharmaceuticals on polar stationary phases are presented.

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Capillary electrochromatographic separation of enantiomers on chemically bonded type of cellulose derivative chiral stationary phases with a positively charged spacer

Cited by 34 publications

References 24 publications

Recent accomplishments in the field of enantiomer separation by CEC

Recent accomplishments in the field of enantiomer separation by CEC

Immobilized Polysaccharide-Based Chiral Stationary Phases for HPLC

Polar stationary phases for capillary electrochromatography

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