HPLC Separation of Enantiomers of Some Chiral Carboxylic Acid Derivatives Using Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases

Matarashvili, Iza; Chankvetadze, Lali; Tsintsadze, Tamar; Farkas, Tamás; Chankvetadze, Bezhan

doi:10.1007/s10337-015-2852-8

Cited by 24 publications

(13 citation statements)

References 40 publications

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“…Quite uncommon finding is the positive effect of temperature on OFLX enantiomeric resolution and selectivity. Unique temperature-induced effect of some other enantiomers was discussed earlier for acidic drugs on polysaccharide-based CSPs 34,35 and amino acids on Cinchona alkaloid-based zwitterionic CSPs. 36,37 Coefficients in Table 1 show that the retention of OFLX enantiomers decreased while resolution and selectivity improved with increasing temperature.…”

Section: Resultsmentioning

confidence: 76%

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Structure‐retention relationship for enantioseparation of selected fluoroquinolones

et al. 2018

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Fluoroquinolones are popular class of antibiotics with distinct chemical functionality. Most of them are ampholytes with one chiral center. Stereogeneic center is located either in the side ring of Gatifloxacin (GFLX) or in the quinolone core of Ofloxacin (OFLX). These two amphoteric fluoroquinolones have terminal amino groups in common. The unusual Nadifloxacin (NFLX) is an acidic fluoroquinolone with a core chiral center. Owing to chirality and functionality differences among GFLX, OFLX, and NFLX, we mapped these enantiomers onto structure-retention relationship. Amount of acetic acid modifier was studied in screened mobile phase and cellulose tris(3-chloro-4-methyl phenyl carbamate) (Lux cellulose-2) stationary phase. Experimental design of acetic acid% along with column temperature have been applied. Resolution and enantioselectivity have been related to structural features of the studied enantiomers. High amount of acid (0.4%) was optimum for the separation of either side chirality with a proximate amino group (GFLX) or core chirality without basic functionality (NFLX), while low amount (0.2%) is optimum for core chiral center with distal amino group (OFLX). Temperature has no significant effect on resolution and retention of enantiomers except for OFLX. Enantio-retention explains possible chiral selective and nonselective interactions. The proposed methods have been validated for pharmaceutical analyses.

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Section: Resultsmentioning

confidence: 76%

“…Quite uncommon finding is the positive effect of temperature on OFLX enantiomeric resolution and selectivity. Unique temperature‐induced effect of some other enantiomers was discussed earlier for acidic drugs on polysaccharide‐based CSPs and amino acids on Cinchona alkaloid‐based zwitterionic CSPs …”

Section: Resultsmentioning

confidence: 82%

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

et al. 2018

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“…The latter case could be explained by the amplified number of theoretical plates owing to improved mass transfer kinetics as the column temperature was increased [27]. The same trend was also observed for the separation of suprofen enantiomers on this type of column using ACN as the mobile phase [26]. On the other columns, however, the decrease in retention and enantioselectivity outperformed the gain in column efficiency, which led to a decrease in resolution (data not shown).…”

Section: Resultsmentioning

confidence: 58%

“…In this mode, only polar organic solvents such as alcohols, ACN, and their mixtures are used as the mobile phase, which has advantages such as short analysis time, high efficiency, favorable peak shape, and improved solubility of analytes [20–22]. Recently, the applicability of polysaccharide‐based CSPs in combination with POSC has successfully resolved many chiral compounds, such as racecadotril, ketorolac, an intermediate of levosimendan, and some carboxylic acid derivatives [23–26], demonstrating their excellent enantiomer separation potential.…”

Section: Introductionmentioning

confidence: 99%

Enantiomeric analysis of simendan on polysaccharide‐based stationary phases by polar organic solvent chromatography

Cheng

Cai

et al. 2020

J of Separation Science

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Herein, the enantiomeric separation of simendan by high-performance liquid chromatography with ultraviolet detection using polysaccharide-based chiral stationary phases in polar organic mode is described. Three chiral columns (Chiralpak AD-H, Chiralcel OD-H, and Chiralpak AS) were screened using pure methanol and acetonitrile without additives under isocratic conditions. A reversed elution order was observed on the Chiralpak AD-H column when the methanol content in the mobile phase (methanol-acetonitrile mixtures) was above 10%, whereby levosimendan eluted prior to dextrosimendan. Further, it was found that increasing temperature effectively improved the enantioresolution on the Chiralpak AD-H column. Van't Hoff analysis was performed to evaluate the contribution of enthalpy and entropy to the chiral discrimination process. The best enantioseparation (α = 3.00, Rs = 12.85) was obtained on the Chiralpak AD-H column with methanol as the mobile phase at 40 • C. Thus, a quantitative method for the resolution of dextrosimendan was established and validated, which could be used as a reference for the determination of dextrosimendan in levosimendan products. K E Y W O R D Schiral stationary phases, enantiomeric separation, polar organic solvent chromatography, quantitative analysis, simendan Enantiomeric analysis of simendan on polysaccharidebased stationary phases by polar organic solvent chromatography.

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“…The chiral selector-dependent reversal of elution order observed between Chiralpak AD and Chiralcel OD column is frequently explained by the conformational difference between the 2 CSPs. [29][30][31] While both polymers have the same side chain (3,5-dimethylphenylcarbamate) and the same monomeric building blocks (1➔4-linked-D-glucopyranose), cellulose presents β, while amylose presents α linkage types. 32 This difference in linkage-type results larger chiral cavities and weaker intrapolymer H-bond in the cellulose derivative, when compared with the amylose-based polymer.…”

Section: Csp and Mobile Phase Screeningmentioning

confidence: 99%

Enantioseparation of racecadotril using polysaccharide‐type chiral stationary phases in polar organic mode

et al. 2017

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Enantioseparation of the antidiarrheal drug, racecadotril, was investigated by liquid chromatography using polysaccharide-type chiral stationary phases in polar organic mode. The enantiodiscrimininating properties of 4 different chiral columns (Chiralpak AD, Chiralcel OD, Chiralpak AS, Chiralcel OJ) with 5 different solvents (methanol, ethanol, 1-propanol, 2-propanol, and acetonitrile) at 5 different temperatures (5-40°C) were investigated. Apart from Chiralpak AS column the other 3 columns showed significant enantioseparation capabilities.Among the tested mobile phases, alcohol type solvents were superior over acetonitrile, and significant differences in enantioselective performance of the selector were observed depending on the type of alcohol employed. Van't Hoff analysis was used for calculation of thermodynamic parameters which revealed that enantioseparation is mainly enthalpy controlled; however, enthropic control was also observed. Enantiopure standard was used to determine the enantiomer elution order, revealing chiral selector-and mobile-phase dependent reversal of enantiomer elution order. Using the optimized method (Chiralcel OJ stationary phase, thermostated at 10°C, 100% methanol, flow rate: 0.6 mL/min) baseline separation of racecadotril enantiomers (resolution = 3.00 ± 0.02) was achieved, with the R-enantiomer eluting first. The method was validated according to the ICH guidelines, and its application was tested on capsule and granules containing the racemic mixture of the drug.

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HPLC Separation of Enantiomers of Some Chiral Carboxylic Acid Derivatives Using Polysaccharide-Based Chiral Columns and Polar Organic Mobile Phases

Cited by 24 publications

References 40 publications

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

Structure‐retention relationship for enantioseparation of selected fluoroquinolones

Enantiomeric analysis of simendan on polysaccharide‐based stationary phases by polar organic solvent chromatography

Enantioseparation of racecadotril using polysaccharide‐type chiral stationary phases in polar organic mode

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