Performance comparison of chlorinated chiral stationary phases in supercritical fluid chromatography for separation of selected pyrrolidone derivatives

Dascălu, Anca‐Elena; Ghinet, Alina; Billamboz, Muriel; Lipka, Emmanuelle

doi:10.1016/j.jpha.2019.03.002

Cited by 4 publications

(1 citation statement)

References 33 publications

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“…Although SFC separations on the latter CSP have been reported [35,36,37], to the best of our knowledge this is the first comparison involving i-Amylose-3. Our results suggest halogen- and hydrogen-bonding to be significant for chiral recognition of chlorinated analytes such as K and its metabolites on chlorinated polysaccharide-based CSPs, which is supported by previous observations concerning achiral chemo-selectivity of halogenated analytes on Amylose-2 [38].…”

Section: Discussionmentioning

confidence: 99%

Subcritical Fluid Chromatography at Sub-Ambient Temperatures for the Chiral Resolution of Ketamine Metabolites with Rapid-Onset Antidepressant Effects

et al. 2019

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Chiral metabolites of ketamine exerting rapid-onset yet sustained antidepressant effects may be marketed directly in the future, but require chemo- and enantio-selective chromatographic methods for quality assurance and control. The chromatographic behavior of S-/R-ketamine, S-/R-norketamine, S-/R-dehydronorketamine, and (2R,6R)-/(2S,6S)-hydroxynorketamine in supercritical fluid chromatography (SFC) was investigated computationally and experimentally with the aim of identifying problematic pairs of enantiomers and parameters for chiral resolution. Retention on three different polysaccharide-based chiral stationary phases (Lux Amylose-2, i-Amylose-3, and i-Cellulose-5) provided new information on the significance of halogen atoms as halogen bond donors and hydrogen bond acceptors for enantioselectivity, which could be corroborated in silico by molecular docking studies. Modifiers inversely affected enantioselectivity and retention. Methanol yielded lower run times but superior chiral resolution compared to 2-propanol. Lower temperatures than those conventionally screened did not impair phase homogeneity but improved enantioresolution, at no cost to reproducibility. Thus, sub-ambient temperature subcritical fluid chromatography (SubFC), essentially low-temperature HPLC with subcritical CO2, was applied. The optimization of the SubFC method facilitated the chiral separation of ketamine and its metabolites, which was applied in combination with direct injection and online supercritical fluid extraction to determine the purity of pharmaceutical ketamine formulations for proof of concept.

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Section: Discussionmentioning

confidence: 99%

Subcritical Fluid Chromatography at Sub-Ambient Temperatures for the Chiral Resolution of Ketamine Metabolites with Rapid-Onset Antidepressant Effects

et al. 2019

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Exploring the application limits of different hold-up time markers in supercritical fluid chromatography

Rédei,

Buratti,

Catani

et al. 2024

Anal Bioanal Chem

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The study focuses on the application range of nitrous oxide as a hold-up time marker in supercritical fluid chromatography (SFC). This compound has been suggested a decade ago to be used as unretained marker, something that the field of SFC was missing for a long time, since its beneficial properties make it an ideal candidate as hold-up time marker. Determination of the hold-up volume and actual volumetric flow rates have always been problematic in SFC due to the compressibility of carbon dioxide and one part of this is the difficulty of hold-up time measurements. Depending on the mobile phase, different methods have been used to measure the hold-up time with varying results. Nitrous oxide and other molecules have been compared in different conditions, mobile phases and stationary phases. In all cases, nitrous oxide gave the lowest elution times. However, detection was difficult in mobile phases containing 10% or more of organic modifier, because most solvents mask the signal of nitrous oxide. Interestingly, the choice of stationary phase also had a slight effect on detection, while different pressure and temperature settings affected each compound in a different manner.

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Enantiorecognition ability of different chiral selectors for separation of liquid crystals in supercritical fluid chromatography; critical evaluation

Vaňkátová

Folprechtová

Kalíková

et al. 2020

Journal of Chromatography A

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Performance comparison of chlorinated chiral stationary phases in supercritical fluid chromatography for separation of selected pyrrolidone derivatives

Cited by 4 publications

References 33 publications

Subcritical Fluid Chromatography at Sub-Ambient Temperatures for the Chiral Resolution of Ketamine Metabolites with Rapid-Onset Antidepressant Effects

Subcritical Fluid Chromatography at Sub-Ambient Temperatures for the Chiral Resolution of Ketamine Metabolites with Rapid-Onset Antidepressant Effects

Exploring the application limits of different hold-up time markers in supercritical fluid chromatography

Enantiorecognition ability of different chiral selectors for separation of liquid crystals in supercritical fluid chromatography; critical evaluation

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