Synthesis of covalently bonded cellulose derivative chiral stationary phases with a bifunctional reagent of 3-(triethoxysilyl)propyl isocyanate

Chen, Xiaoming; Liu, Yueqi; Qin, Feng; Kong, Liang; Zou, Hanfa

doi:10.1016/s0021-9673(03)01104-x

Cited by 69 publications

(25 citation statements)

References 17 publications

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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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“…[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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“…The methods used to render the polysaccharide derivatives insoluble in any mobile phase solvents are based on two general approaches: the direct covalent linkage of the derivative on the support [14,15] or the reticulation of the polysaccharide by a cross linking reaction [13,16]. Some of the reported immobilisation technologies aimed to combine both strategies [17][18][19].…”

Section: Introductionmentioning

confidence: 99%

Pharmacokinetic Development of a Sensitive and Stereoselective HPLC Method for the Analysis of Pindolol in Plasma and Pharmaceutical Products Using a Chiralpak IB Column and Fluorescence Detection

Hefnawy¹,

Kassem²,

Abdine³

et al. 2009

Sci. Pharm.

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A sensitive and stereoselective HPLC method has been developed for the simultaneous determination of pindolol enantiomers in plasma and pharmaceutical products. Enantiomeric resolution was achieved on a cellulose tris(3,5-dimethylphenylcarbamate) immobilized onto a 5 µm spherical porous silica chiral stationary phase (CSP) known as Chiralpak IB with fluorescence detection set at 266 nm for excitation and 308 nm for emission. The mobile phase consists of n-hexane-isopropanol-triethylamine, (50:50:0.5), (v/v/v) has been used at a flow rate of 1.0 ml/min. The method was highly specific where other coformulated drugs such as clopamide and isosorbide did not interfere. The stability of pindolol enantiomers under different degrees of temperature was studied. The method validated for its linearity, accuracy, precision and robustness. There was no significant difference (p>0.05) between inter-and intra-day studies for each enantiomers which confirmed the reproducibility of the assay method. Preliminary data suggest that S-(−)-pindolol induces less bradycardia but more sedation and central nervous system depression than racemic pindolol.

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“…To overcome this defect, the polysaccharide derivatives have been chemically bonded to a silica matrix and have been used extensively as chiral stationary phase. [6][7][8][9][10] A new generation of CSPs for HPLC using a novel immobilization technology has been recently launched. Thus, Chiralpak IA, a 3,5-dimethylphenylcarbamate derivative of amylose, immobilized onto silica (the immobilized version of Chiralpak AD) was the first launched in this series followed by Chiralpak IB, a 3,5-dimethylphenylcarbamate derivative of cellulose (the immobilized version of Chiralcel OD).…”

Section: Introductionmentioning

confidence: 99%

Chiral recognition ability and solvent versatility of bonded amylose tris(3,5‐dimethylphenylcarbamate) chiral stationary phase: Enantioselective liquid chromatographic resolution of racemic N‐alkylated barbiturates and thalidomide analogs

Ghanem

Al‐Humaidi

2007

Chirality

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The chiral recognition ability and solvent versatility of a new chiral stationary phase containing amylose 3,5-dimethylphenylcarabamate immobilized onto silica gel (CHIRALPAK IA) is investigated. Thus, the direct enantioselective separation of a set of racemic N-alkylated barbiturates and 3-alkylated analogs of thalidomide was conducted using different nonstandard solvents as eluent and diluent, respectively in high-performance liquid chromatography (HPLC). The separation, resolution, and elution order of the investigated compounds were compared on both immobilized and coated amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak IA and Chiralpak AD, respectively) using a mixture of n-hexane/2-propanol (90:10 v/v) as mobile phase with different flow-rates and fixed UV detection at 254 nm. The effect of the immobilization of the amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase on silica (Chiralpak IA) on the chiral recognition ability was noted as the bonded phase (Chiralpak IA) was superior in chiral recognition and possesses a higher resolving power in most of the reported cases than the coated one (Chiralpak AD). A few racemates were not or poorly resolved on the immobilized Chiralpak IA or the coated Chiralpak AD when using standard solvents were most efficiently resolved on the immobilized Chiralpak IA upon using nonstandard solvents. Furthermore, the immobilized phase withstands the nonstandard (prohibited) HPLC solvents such as dichloromethane, ethyl acetate, tetrahydrofuran, methyl-tert-butyl ether, and others when used as eluents or as a dissolving agent for the analyte itself. The direct analysis of a real sample extracted from plasma using DCM on Chiralpak IA is also shown.

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Synthesis of covalently bonded cellulose derivative chiral stationary phases with a bifunctional reagent of 3-(triethoxysilyl)propyl isocyanate

Cited by 69 publications

References 17 publications

Immobilized Polysaccharide-Based Chiral Stationary Phases for HPLC

Immobilized Polysaccharide-Based Chiral Stationary Phases for HPLC

Pharmacokinetic Development of a Sensitive and Stereoselective HPLC Method for the Analysis of Pindolol in Plasma and Pharmaceutical Products Using a Chiralpak IB Column and Fluorescence Detection

Chiral recognition ability and solvent versatility of bonded amylose tris(3,5‐dimethylphenylcarbamate) chiral stationary phase: Enantioselective liquid chromatographic resolution of racemic N‐alkylated barbiturates and thalidomide analogs

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