Solvent versatility of immobilized 3,5-dimethylphenylcarbamate of amylose in enantiomeric separations by HPLC

Zhang, Tong; Kientzy, Christophe; Franco, Pilar; Ohnishi, Akira; Kagamiharb, Yasuhiro; Kurosawa, Hidehiro

doi:10.1016/j.chroma.2005.03.116

Cited by 190 publications

(119 citation statements)

References 29 publications

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“…[42]. This is also true with the immobilized ones [20][21][22]. For example, enantioselectivity for pindolol on Chiralpak IB further improved by simply replacing 10% 2-PrOH in hexane and significantly enhanced by using 50% 2-PrOH in hexane.…”

Section: Structures Of (A) S-(−)-pindolol (B) R-(+)-pindolol and (C)mentioning

confidence: 48%

“…Chiralpak IA and Chiralpak IB have as a common feature the chiral selector immobilised onto silica gel. Owing to their immobilised nature, these CSPs exhibit excellent solvent versatility: they can be used with mobile phases of various natures, ranging from alcohol mixtures in alkanes to mobile phases containing MtBE, THF, chlorinated solvents and EtOAc, among others [20][21][22]. They can also be used under reversed-phase conditions, combining miscible polar organic solvents with aqueous solutions [37].It has been widely perceived that, with the coated polysaccharide-based CSPs, the modification in mobile phase composition may induce significant effects on various chromatographic parameters (retention, enantioselectivity, resolution, elution order, etc.)…”

Section: Structures Of (A) S-(−)-pindolol (B) R-(+)-pindolol and (C)mentioning

confidence: 99%

“…That is, tris(3,5-dimethylphenylcarbamate) of amylose for Chiralpak IA and tris(3,5-dimethylphenylcarbamate) of cellulose for Chiralpak IB. The main characteristics of these two CSPs have been discussed in diverse publications [20][21][22].…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Structures Of (A) S-(−)-pindolol (B) R-(+)-pindolol and (C)mentioning

confidence: 48%

Section: Structures Of (A) S-(−)-pindolol (B) R-(+)-pindolol and (C)mentioning

confidence: 99%

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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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“…[64][65][66][67][68][69][70][71][72][73][74][75][76] For example, topologically interesting catenanes, 67 molecular knots, 71,72 and knotaxane, 73 which is rotaxane with knots as stoppers, have been completely resolved on CSP-32 using a hexane/chloroform/2-propanol mix- ture ( Figure 18). In addition, the linear, branched, and cyclic knotane oligomers can be sufficiently resolved with an eluent containing chloroform ( Figure 19).…”

Section: Enantioseparations With Eluents Containing Chclmentioning

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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“…그런데 이들 다당류 유도체를 이용한 키랄 컬럼들은 실리카 모체에 키랄선택자로 사용된 셀루로 오스와 아밀로오스의 유도체를 흡착하여 제조되었기 때문에 순상 (normal phase) 크로마토그래피에서 실험할 경우, 여러 종류의 이동상 용매를 사용할 수 없는 컬럼의 단점을 가지고 있을 뿐만 아니라 키랄선택자를 흡착된 컬럼의 특성상 이들 컬럼의 안정성과 재현성의 여러 단점들이 보고되었다 [2][3][4][5]. 그런 결점들을 극복하기 위해 키랄선택자인 다당류 유도체 를 공유결합으로 고정시킨 컬럼들이 그 이후에 개발되었는 데, 이러한 키랄선택자가 공유결합된 키랄 컬럼들을 이용한 순상 크로마토그래피에서 기존의 키랄선택자가 흡착된 키랄 컬럼에서는 허용되지 않았던 halogenated solvents 같은 용매 들을 이동상으로 사용한 여러 연구들이 보고되었다 [4][5][6][7][8][9]. 최 근 amylose tris(3,5-dichlorophenylcarbamate)을 키랄선택자 로 사용하여 실리카 젤에 공유결합된 새로운 Chiralpak IE 키 랄컬럼이 소개되었다 [10][11][12].…”

Section: Introductionunclassified

Simultaneous Enantiomer Separation of α-Amino Acids and Their Esters as Fluorenylmethoxycarbonyl Derivatives under UV and Fluorescence Detection by High Performance Liquid Chromatography

포크롤¹,

이원재

2015

KSBB Journal

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Liquid chromatographic enantiomer separation of α-amino acids and their methyl and ethyl esters as fluorenylmethoxycarbonyl (FMOC) derivatives was performed using a recently developed chiral column (Chiralpak IE) based on polysaccharide derivative under simultaneous UV detection and fluorescence detection. The degree of enantiomer separation of α-amino acid esters as FMOC derivatives is generally higher than that of the corresponding α-amino acids. Especially, α-amino acid methyl esters showed the greatest enantioseparation. As this method developed in this study can be applied to determine the chemical and optical purity of α-amino acids and esters, it is expected to be quite useful for their chiral separation using Chiralpak IE.

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Solvent versatility of immobilized 3,5-dimethylphenylcarbamate of amylose in enantiomeric separations by HPLC

Cited by 190 publications

References 29 publications

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

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

Immobilized Polysaccharide-Based Chiral Stationary Phases for HPLC

Simultaneous Enantiomer Separation of α-Amino Acids and Their Esters as Fluorenylmethoxycarbonyl Derivatives under UV and Fluorescence Detection by High Performance Liquid Chromatography

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