Combined use of isopropylamine and trifluoroacetic acid in methanol-containing mobile phases for chiral supercritical fluid chromatography

Klerck, Katrijn De; Mangelings, Debby; Clicq, David; Boever, Filip De; Heyden, Yvan Vander

doi:10.1016/j.chroma.2011.11.023

Cited by 54 publications

(18 citation statements)

References 18 publications

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“…Our research group recently investigated the combined use of isopropylamine (IPA) and trifluoroacetic acid (TFA) in methanolcontaining mobile phases for the separation of basic, acidic, neutral and amphoteric pharmaceuticals on polysaccharide-based CSPs [88]. It was found that with a combination of IPA and TFA in the mobile phase different and broader enantioselectivities are obtained compared to the separate use of IPA for basic analytes or TFA for acidic analytes.…”

Section: Mobile Phasementioning

confidence: 99%

“…The combination of these two additives resulted in the separation of compounds that could not be resolved when only one additive was used (Fig. 5) [88,89].…”

Section: Mobile Phasementioning

confidence: 99%

“…After applying this screening approach on a test set of 40 pharmaceuticals, a success rate of 38 separated compounds (of which 28 were baseline separated) was reached. New methanol-based mobile phases and new polysaccharide-based chiral stationary phases were tested in our group to assess their applicability in an updated version of the screening strategy originally defined by Maftouh et al [18,88,89]. Combining isopropylamine and trifluoroacetic acid in one mobile phase with 20% methanol as modifier leads to higher success rates within 30 min.…”

Section: Screening Strategiesmentioning

confidence: 99%

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Supercritical fluid chromatography for the enantioseparation of pharmaceuticals

Klerck

Mangelings

Heyden

2012

Journal of Pharmaceutical and Biomedical Analysis

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167

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Section: Mobile Phasementioning

confidence: 99%

“…The combination of these two additives resulted in the separation of compounds that could not be resolved when only one additive was used (Fig. 5) [88,89].…”

Section: Mobile Phasementioning

confidence: 99%

Section: Screening Strategiesmentioning

confidence: 99%

See 1 more Smart Citation

Supercritical fluid chromatography for the enantioseparation of pharmaceuticals

Klerck

Mangelings

Heyden

2012

Journal of Pharmaceutical and Biomedical Analysis

Self Cite

167

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“…We did not observe the general effect of enhanced and decreased enantioselectivity on the cellulose-based and amylose-based CSPs, respectively, caused with the dual additives in the SFC separation systems that were reported by other authors. 28 It is obvious from Table 2 and Table S1 that different groups of tested analytes prefer different CSPs-polysaccharide backbone compared in this work.…”

Section: Resultsmentioning

confidence: 97%

Enantioselective potential of polysaccharide‐based chiral stationary phases in supercritical fluid chromatography

2017

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The enantioselective potential of two polysaccharide-based chiral stationary phases for analysis of chiral structurally diverse biologically active compounds was evaluated in supercritical fluid chromatography using a set of 52 analytes. The chiral selectors immobilized on 2.5 μm silica particles were tris-(3,5-dimethylphenylcarmabate) derivatives of cellulose or amylose. The influence of the polysaccharide backbone, different organic modifiers, and different mobile phase additives on retention and enantioseparation was monitored. Conditions for fast baseline enantioseparation were found for the majority of the compounds. The success rate of baseline and partial enantioseparation with cellulose-based chiral stationary phase was 51.9% and 15.4%, respectively. Using amylose-based chiral stationary phase we obtained 76.9% of baseline enantioseparations and 9.6% of partial enantioseparations of the tested compounds. The best results on cellulose-based chiral stationary phase were achieved particularly with propane-2-ol and a mixture of isopropylamine and trifluoroacetic acid as organic modifier and additive to CO , respectively. Methanol and basic additive isopropylamine were preferred on amylose-based chiral stationary phase. The complementary enantioselectivity of the cellulose- and amylose-based chiral stationary phases allows separation of the majority of the tested structurally different compounds. Separation systems were found to be directly applicable for analyses of biologically active compounds of interest.

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“…Since methanol is the most polar of the alcohols which may offer strong enough eluent strength for the analytes, and considering that the sample is dissolved in methanol as well, we first selected methanol as the cosolvent. As referred to numerous previous studies on the enantioselective separation of basic molecules, either basic additives (ammonium hydroxide, dimethylamine) and/or acidic additives (formic acid, acetic acid, and TFA) were used to improve chiral separation efficiency and/or chromatographic peak shapes . Thus, under the same elution gradient, methanol, 0.05% NH 3 ·H 2 O in methanol, and 0.05% formic acid in methanol were evaluated as the cosolvent.…”

Section: Resultsmentioning

confidence: 99%

Enantioseparation of nornicotine in tobacco by ultraperformance convergence chromatography with tandem mass spectrometry

Deng

Wang

Bian

et al. 2017

J of Separation Science

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Nornicotine, an alkaloid constituent of tobacco, is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco. Accumulating evidence reveals that nornicotine enantiomers have different neurochemical and behavioral effects. In the present study, an accurate and rapid method was developed for the enantioseparation of (R)-(+)-nornicotine and (S)-(-)-nornicotine enantiomers in tobacco by ultra-performance convergence chromatography with tandem mass spectrometry. Chromatographic conditions were investigated to achieve the optimal resolution of two enantiomers. Results indicated that (R)-(+)-nornicotine and (S)-(-)-nornicotine could be separated within 5 min when ammonium hydroxide was added into the cosolvent, and the best resolution (R = 4.76) was achieved on a immobilized cellulose tris-(3,5-dichlorophenylcarbamate) chiral stationary phase. The proposed method was validated and was finally applied to analyze the compositions of (R)-(+)-nornicotine and (S)-(-)-nornicotine in three typical types of tobaccos (flue-cured, burley, and oriental). It was found that, enantiomer fraction of nornicotine (the proportion of (S)-(-)-nornicotine in the nornicotine pool) in burley tobacco samples was relatively high and constant compared with flue-cured and oriental tobaccos. The effective and rapid enantioseparation of nornicotine may help the understanding of alkaloid metabolites in different tobacco varieties and may also benefit pharmacological studies of alkaloid enantiomers.

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Combined use of isopropylamine and trifluoroacetic acid in methanol-containing mobile phases for chiral supercritical fluid chromatography

Cited by 54 publications

References 18 publications

Supercritical fluid chromatography for the enantioseparation of pharmaceuticals

Supercritical fluid chromatography for the enantioseparation of pharmaceuticals

Enantioselective potential of polysaccharide‐based chiral stationary phases in supercritical fluid chromatography

Enantioseparation of nornicotine in tobacco by ultraperformance convergence chromatography with tandem mass spectrometry

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