Insights into chiral recognition mechanisms in supercritical fluid chromatography V. Effect of the nature and proportion of alcohol mobile phase modifier with amylose and cellulose tris-(3,5-dimethylphenylcarbamate) stationary phases

Khater, Syame; West, Caroline

doi:10.1016/j.chroma.2014.11.033

Cited by 51 publications

(25 citation statements)

References 40 publications

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“…The change of retention factor is basically in accordance with that of the polarity of modifier and the space resistance. In conclusion, methanol usually provided the largest success rate and specificity, which agreed well with the report of Syame Khater …”

Section: Resultssupporting

confidence: 91%

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

et al. 2018

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Mandelic acid and its derivatives are important chiral analogs which are widely used in the pharmaceutical synthetic industry. The present study investigated the enantiomeric separation of six mandelic acids (mandelic acid, 2‐chloromandelic acid, 3‐chloromandelic acid, 4‐chloromandelic acid, 4‐bromomandelic acid, 4‐methoxymandelic acid) on the Chiralpak AD‐3 column by supercritical fluid chromatography. The influences of volume fraction of trifluoroacetic acid, type and percentage of modifier, column temperature, and backpressure on the separation efficiency were investigated. And the enantiomer elution order was determined. The results show that, for a given modifier, the retention factor, the separation factor, and the separation resolution decreased gradually with increasing the volume ratio of the modifier. At the same volume ratio of modifier, the retention factor of the mandelic acid and its derivatives increased in the order of methanol, ethanol, and isopropanol, except 3‐chloromandelic acid. The separation factor and the separation resolution decreased with the increase of column temperature (below the temperature limit). The backpressure affected the enantioseparation process: As the backpressure increased, a corresponding decrease in retention factor was observed. Under the same chiral column conditions, the SFC method exhibited faster and more efficient separation with better enantioselectivity than the HPLC method.

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Section: Resultssupporting

confidence: 91%

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

et al. 2018

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“…The temperature can affect the elution strength and mobile phase viscosity and thus allows achieving very high efficiency. Detailed descriptions of various effects of the separation system variables and their consequences for the separation performance in SFC can be found in papers and reviews by the group of West and Lesellier [5,[19][20][21][22][23].…”

Section: Introductionmentioning

confidence: 99%

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

Kalíková

Martínková

Schmid

et al. 2018

J of Separation Science

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A cellulose tris-(3,5-dimethylphenylcarbamate)-based chiral stationary phase was studied as a tool for the enantioselective separation of 21 selected analytes with different pharmaceutical and physicochemical properties. The enantioseparations were performed using supercritical fluid chromatography. The effect of the mobile phase composition was studied. Four different additives (diethylamine, triethylamine, isopropylamine, and trifluoroacetic acid) and isopropylamine combined with trifluoroacetic acid were tested and their influence on enantioseparation was compared. The influence of two different mobile phase co-solvents (methanol and propan-2-ol) combined with all the additives was also evaluated. The best mobile phase compositions for the separation of the majority of enantiomers were CO /methanol/isopropylamine 80:20:0.1 v/v/v or CO /propan-2-ol/isopropylamine/trifluoroacetic acid 80:20:0.05:0.05 v/v/v/v. The best results were obtained from the group of basic β-blockers. A high-performance liquid chromatography separation system composed of the same stationary phase and mobile phase of similar properties prepared as a mixture of hexane/propan-2-ol/additive 80:20:0.1 v/v/v was considered for comparison. Supercritical fluid chromatography was found to yield better results, i.e. better enantioresolution for shorter analysis times than high-performance liquid chromatography. However, examples of enantiomers better resolved under the optimized conditions in high-performance liquid chromatography were also found.

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“…1‐PrOH, 2‐PrOH, EtOH, BuOH, t ‐BuOH) as mobile phase (Al‐Othman, Ali, Asim, & Khan, ; Chankvetadze, ; Ikai & Okamoto, ; Okamoto & Yashima, ). To regulate retention and selectivity in NP LC (Gyllenhaal & Stefansson, ; Matarashvili, Chankvetadze, Fanali, Farkas, & Chankvetadze, ; Xiang et al, ) or in SFC (Aranyi, Ilisz, Péter, Fülöp, & West, ; Khater & West, ; Su, Bao, Xing, Yang, & Ren, ; Toribio, del Nozal, Bernal, Bernal, & Martin, ), the variation in the nature and concentration of an alcohol modifier is frequently explored. The effect of the nature of alcohol modifiers on chromatographic parameters was investigated for analytes 2 and 4 on Lux Amylose‐2 and Lux i‐Cellulose‐5 CSPs.…”

Section: Resultsmentioning

confidence: 99%

Chiral high‐performance liquid and supercritical fluid chromatographic enantioseparations of limonene‐based bicyclic aminoalcohols and aminodiols on polysaccharide‐based chiral stationary phases

Orosz

Bajtai

Lê

et al. 2019

Biomedical Chromatography

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Enantioseparation of limonene‐based bicyclic 1,3‐aminoalcohols and 1,3,5‐ and 1,3,6‐aminodiols was performed by normal‐phase high‐performance liquid chromatographic and supercritical fluid chromatographic (SFC) methods on polysaccharide‐based chiral stationary phases. The effects of the composition of the mobile phase, the column temperature and the structures of the analytes and chiral selectors on retention and selectivity were investigated by normal‐phase LC and SFC technique. Thermodynamic parameters derived from selectivity–temperature‐dependence studies were found to be dependent on the chromatographic method applied, the nature of the chiral selector and the structural details of the analytes. Enantiorecognition in most cases was enthalpically driven but an unusual temperature behavior was also observed: decreased retention times were accompanied by improved separation factors with increasing temperature, i.e. some entropically driven separations were also observed. The elution sequence was determined in all cases. The separation of the stereoisomers was optimized in both chromatographic modalities.

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Insights into chiral recognition mechanisms in supercritical fluid chromatography V. Effect of the nature and proportion of alcohol mobile phase modifier with amylose and cellulose tris-(3,5-dimethylphenylcarbamate) stationary phases

Cited by 51 publications

References 40 publications

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

Enantioseparation of chiral mandelic acid derivatives by supercritical fluid chromatography

Cellulose tris‐(3,5‐dimethylphenylcarbamate)‐based chiral stationary phase for the enantioseparation of drugs in supercritical fluid chromatography: comparison with HPLC

Chiral high‐performance liquid and supercritical fluid chromatographic enantioseparations of limonene‐based bicyclic aminoalcohols and aminodiols on polysaccharide‐based chiral stationary phases

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