Contribution of preparative chromatographic resolution to the investigation of chiral phenomena

Francotte, Eric

doi:10.1016/0021-9673(94)80419-2

Cited by 143 publications

(71 citation statements)

References 159 publications

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“…Hesse and Hagel [101] discovered that microcrystalline cellulose triacetate (CTA-I) produces a tertiary structure upon swelling and forms chiral cavities which are able to include stereoselectively compounds with aromatic residues. Several compounds were resolved on CTA-I [102,103]. Okamoto's group [104,105] prepared cellulose triacetate in a different way and coated macroporous aminopropylsilanized silica gel with the biopolymer.…”

Section: Direct Methodsmentioning

confidence: 99%

Chiral separation by chromatographic and electromigration techniques. A Review

Gübitz

Schmid

2001

Biopharm & Drug Disp

227

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

227

135

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“…This stationary phase was developed primarily by the Okamoto group (Okamoto and Kaida, 1990;Okamoto and Kaida, 1994;Okamoto and Ikai, 2008) and has been successfully used to separate several chiral molecules (Silva Jr. et al, 2012;Francotte, 1994;Francotte, 2001;Lourenço et al, 2012). The chemical structure of the chiral selector is depicted in Figure 2.…”

Section: Figure 1: Chemical Structures Of Verapamil Enantiomers: (A) mentioning

confidence: 99%

Chromatographic Separation of Verapamil Racemate Using a Varicol Continuous Multicolumn Process

Cremasco

Santana²

2015

Braz. J. Chem. Eng.

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-Verapamil is a chiral drug that is marketed in its racemic form, but because of the pharmacological effects due to molecule's chirality, one of the enantiomers is more potent, and the other exhibits different activities of therapeutic interest. The preparative separation of the verapamil enantiomers was performed using a continuous Varicol unit operated on a scale of 1 g/day. Amylose tris(3,5-dimethylphenylcarbamate) functioned as the stationary phase, and n-hexane/isopropanol/ethanol mixtures were used as the mobile phase. Diethylamine was used as the additive. The enantiomeric purities were 93.0% for S-(-)-verapamil and 92.0% for R-(+)-verapamil in the raffinate and extract streams, respectively. The unit provided productivities of 0.18 kg of raffinate per day per kg of adsorbent and 0.20 kg of extract per day per kg of adsorbent when using a feed concentration of 12.5 g L -1 .

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Section: Introductionmentioning

confidence: 99%

“…10,22 For a large scale preparative separation, good solubility of the sample is essential for high productivity. [22][23][24][25] Therefore, versatility in the solvent selection is highly desired.This problem can be solved through immobilization of the polysaccharide derivatives onto chromatographic supports. Once CSPs are immobilized on a support, a number of solvents can be used as the mobile phases.…”

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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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Contribution of preparative chromatographic resolution to the investigation of chiral phenomena

Cited by 143 publications

References 159 publications

Chiral separation by chromatographic and electromigration techniques. A Review

Chiral separation by chromatographic and electromigration techniques. A Review

Chromatographic Separation of Verapamil Racemate Using a Varicol Continuous Multicolumn Process

Immobilized Polysaccharide-Based Chiral Stationary Phases for HPLC

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