Enantiomer elution order reversal of fluorenylmethoxycarbonyl-isoleucine in high-performance liquid chromatography by changing the mobile phase temperature and composition

Chankvetadze, Lali; Ghibradze, N.; Karchkhadze, M.; Peng, Liming; Farkas, Tamás; Chankvetadze, Bezhan

doi:10.1016/j.chroma.2011.06.068

Cited by 67 publications

(34 citation statements)

References 16 publications

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“…It must be noted that alcohol modifier concentration‐dependent reversal of EEO is not limited to amylose‐based chiral columns. Similar effect was recently reported for FMOC‐isoleucine on the cellulose‐based chiral column Lux Cellulose‐1 . In the present study, the reversal of EEO of naproxen was observed on two amylose‐based columns, ADMPC (data not shown) and Lux Amylose‐2 (Fig.…”

Section: Resultssupporting

confidence: 90%

“…S3). Comparative EEO has not been studied systematically on these two kinds of cellulose derivatives previously but in one case the opposite EEO on cellulose benzoate and some carbamate‐based CSPs has been reported for FMOC‐isoleucine .…”

Section: Resultsmentioning

confidence: 99%

“…Not only the nature of the alcohol modifier but also its concentration in a given mobile phase can affect the EEO . The first example of such EEO reversal was reported by Balmer et al in 1992 for an amino alcohol drug candidate on Chiralpak AD .…”

Section: Resultsmentioning

confidence: 99%

“…the temperature at which such compensation occurs is usually above the practical temperature range of most HPLC separations. For this reason, rather few examples of temperature‐dependent reversal of EEO in HPLC are described in the literature (see, e.g …”

Section: Resultsmentioning

confidence: 99%

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HPLC separation of enantiomers of chiral arylpropionic acid derivatives using polysaccharide‐based chiral columns and normal‐phase eluents with emphasis on elution order

Matarashvili

Chankvetadze

Fanali³

et al. 2013

J of Separation Science

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The separation of enantiomers of ten chiral arylpropionic acid derivatives was studied on six different polysaccharide-based chiral HPLC columns with various normal-phase eluents. Along with the successful separation of analyte enantiomers, the emphasis of this study was on the effect of the chiral selector and mobile phase composition as well as of the separation temperature on the elution order of enantiomers. The interesting phenomena of reversal of enantiomer elution order function of the polysaccharide backbone (cellulose or amylose), type of derivative (carbamate or benzoate), nature and position of the substituent(s) in the phenylcarbamate moiety, the polar modifier of the mobile phase (ethanol or 2-propanol), its content in the mobile phase, and separation temperature were investigated. In addition, an unusual increase in retention with increasing temperature was observed for some arylpropionic acid derivatives.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

HPLC separation of enantiomers of chiral arylpropionic acid derivatives using polysaccharide‐based chiral columns and normal‐phase eluents with emphasis on elution order

Matarashvili

Chankvetadze

Fanali³

et al. 2013

J of Separation Science

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show abstract

“…Column temperature may have a significant impact on the adsorption – desorption equilibrium between enantiomers and CSPs, further leading to a potentially big change of retention behaviors, resolution, and elution order of enantiomers on CSPs. A thermodynamic study is an effective method to investigate chiral recognition mechanism . The effect of column temperature on separation of chiral analytes can be expressed by Van't Hoff equations as follows:

ln k = - \frac{normalΔ H}{RT} + \frac{normalΔ S}{R} + ln normalΦ = - \frac{normalΔ H}{RT} + normalΔ S^{*}

…”

Section: Resultsmentioning

confidence: 99%

Reliable HPLC separation, vibrational circular dichroism spectra, and absolute configurations of isoborneol enantiomers

et al. 2017

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Resolution of chiral compounds has played an important role in the pharmaceutical field, involving detailed studies of pharmacokinetics, physiological, toxicological, and metabolic activities of enantiomers. Herein, a reliable method by high-performance liquid chromatography (HPLC) coupled with an optical rotation detector was developed to separate isoborneol enantiomers. A cellulose tris(3, 5-dimethylphenylcarbamate)-coated chiral stationary phase showed the best separation performance for isoborneol enantiomers in the normal phase among four polysaccharide chiral packings. The effects of alcoholic modifiers and column temperature were studied in detail. Resolution of the isoborneol racemate displayed a downward trend along with an increase in the content of ethanol and column temperature, indicating that less ethanol in the mobile phase and lower temperature were favorable to this process. Moreover, two isoborneol enantiomers were obtained via a semipreparative chiral HPLC technique under optimum conditions, and further characterized by analytical HPLC, and experimental and calculated vibrational circular dichroism (VCD) spectroscopy, respectively. The solution VCD spectrum of the first-eluted component was consistent with the Density Functional Theory (DFT) calculated pattern based on the SSS configuration, indicating that this enantiomer should be (1S, 2S, 4S)-(+)-isoborneol. Briefly, these results have provided reliable information to establish a method for analysis, preparative separation, and absolute configuration of chiral compounds without typical chromophoric groups.

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Effect of Chromatographic Conditions on Enantioseparation of Bovine Serum Albumin Chiral Stationary Phase in HPLC and Thermodynamic Studies

Wang

Xiong

et al. 2013

Chirality

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Twelve chiral compounds were enantiomerically resolved on bovine serum albumin chiral stationary phase (BSA-CSP) by high-performance liquid chromatography (HPLC) in reversed-phase modes. Chromatographic conditions such as mobile phase pH, the percentage of organic modifier, and concentration of analyte were optimized for separation of enantiomers. For N-(2, 4-dinitrophenyl)-serine (DNP-ser), the retention factors (k) greatly increase from 0.81 to 6.23 as the pH decreasing from 7.21 to 5.14, and the resolution factor (R(s)) exhibited a similar increasing trend (from 0 to 1.34). More interestingly, the retention factors for N-(2, 4-dinitrophenyl)-proline (DNP-pro) decrease along with increasing 1-propanol in mobile phase (3%, 5%, 7% and 9% by volume), whereas the resolution factor shows an upward trend (from 0.96 to 2.04). Moreover, chiral recognition mechanisms for chiral analytes were further investigated through thermodynamic methods.

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Enantiomer elution order reversal of fluorenylmethoxycarbonyl-isoleucine in high-performance liquid chromatography by changing the mobile phase temperature and composition

Cited by 67 publications

References 16 publications

HPLC separation of enantiomers of chiral arylpropionic acid derivatives using polysaccharide‐based chiral columns and normal‐phase eluents with emphasis on elution order

HPLC separation of enantiomers of chiral arylpropionic acid derivatives using polysaccharide‐based chiral columns and normal‐phase eluents with emphasis on elution order

Reliable HPLC separation, vibrational circular dichroism spectra, and absolute configurations of isoborneol enantiomers

Effect of Chromatographic Conditions on Enantioseparation of Bovine Serum Albumin Chiral Stationary Phase in HPLC and Thermodynamic Studies

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