Chiral Chromatographic Discrimination Ability of a Cellulose 3,5-Dimethylphenylcarbamate/10-Undecenoate Mixed Derivative Fixed on Several Chromatographic Matrices

Oliveros, Laureano; López, Pilar; Minguillón, Cristina; Franco, Pilar

doi:10.1080/10826079508009292

Cited by 100 publications

(39 citation statements)

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“…A slightly lower chiral recognition compared to the coated-type phases was observed with these CSPs. Oliveros et al [119] published a procedure for covalent binding by polymerization of mixed polysaccharide derivatives containing a 3,5-dimethylphenylcarbamate group and a 10-undecenoate spacer. Enomoto et al [117] described the immobilization of amylose to silica by reducing the terminal residue of each molecule involving an enzymatic polymerization of a-d-glucose-1-phosphate.…”

Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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This review gives a survey of different chiral separation principles and their use in high-performance liquid chromatography (HPLC), gas chromatography (GC), supercritical fluid chromatography (SFC), thin-layer chromatography (TLC), capillary electrophoresis (CE) and capillary electrochromatography (CEC) highlighting new developments and innovative techniques. The mechanisms of the different separation principles are briefly discussed and some selected applications are shown.

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Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

225

135

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“…42,43 They prepared a polysaccharide derivative bearing both 3,5-dimethylphenylcarbamate and 10-undecenoyl groups as the polymerizable group.…”

Section: Immobilization Of Polysaccharide Derivatives Having Vinyl Grmentioning

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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“…2 Recently, the linkage of a cellulose derivative, bearing 3,5-dimethylphenylaminocarbonyl and 10-undecenoyl groups at the same time, by heating without solvent with different chromatographic matrices has been described. 3,4 The linkage takes place via the 10-undecenoyl groups either by reaction with allyl groups on the silica gel (heteregeneous coupling of double bonds) or by reticulation of the 10-undecenoyl groups themselves on nonfunctionalized matrices, such as silica gel, alumina, or graphite. The resulting CSPs are resistant to the usual solvents used in liquid chromatography and show good enantioselectivity, particularly when the cellulose derivative is fixed covalently to allyl silica gel.…”

mentioning

confidence: 99%