Analytical and semipreparative chiral separation of<i>cis</i>-itraconazole on cellulose stationary phases by high-performance liquid chromatography

Kurka, Ondřej; Kučera, Lukáš; Bednář, Petr

doi:10.1002/jssc.201600240

Cited by 15 publications

(7 citation statements)

References 31 publications

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“…The resolving abilities of the obtained CSPs were evaluated using the racemates shown in Figure 6: Tröger's base (2), (6), cobalt (III) tris(acetylacetonate) (7), flavanone (8), and transcyclopropanedicarboxylic acid dianilide (9). The chromatogram for resolution of racemate 7 on 1a is shown in Figure 7 with hexane/2-propanol (90:10, v/v) as mobile phase.…”

Section: Chiral Recognition Of Novel Amylose Derivativesmentioning

confidence: 99%

“…For their distinguished chiral recognition abilities, polysaccharide derivatives, especially the benzoates and phenylcarbamates of cellulose and amylose, are recognized as the most powerful chiral stationary phases (CSPs) in high-performance liquid chromatography (HPLC). [1][2][3][4][5][6][7][8][9][10] Generally, these derivatives are homogeneously substituted, which means that they bear the same substituent at 2-, 3-, and 6-positions of a glucose ring. The heterosubstituted polysaccharide derivatives having different substituents at 2, 3positions and 6-position has also been obtained.…”

Section: Introductionmentioning

confidence: 99%

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Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

et al. 2017

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Six novel regioselectively substituted amylose derivatives with a benzoate at 2-position and two different phenylcarbamates at 3- and 6-positions were synthesized and their structures were characterized by H nuclear magnetic resonance (NMR) spectroscopy. Their enantioseparation abilities were then examined as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) after they were coated on 3-aminopropyl silica gels. Investigations indicated that the substituents at the 3- and 6-positions played an important role in chiral recognition of these amylose 2-benzoate serial derivatives. The derivatives demonstrated characteristic enantioseparation and some racemates were better resolved on these derivatives than on Chiralpak AD, which is one of the most efficient CSPs, utilizing coated amylose tris(3,5-dimethylphenylcarbamate) as the chiral selector. Among the derivatives prepared, amylose 2-benzoate-3-(phenylcarbamate/4-methylphenylcarbamate)-6-(3,5-dimethylphenylcarbamate) exhibited chiral recognition abilities comparable to that of Chiralpak AD and may be useful CSPs in the future. The effect of mobile phase on chiral recognition was also studied. In general, with the decreased concentration of 2-propanol, better resolutions were obtained with longer retention times. Moreover, when ethanol was used instead of 2-propanol, poorer resolutions were often achieved. However, in some cases, improved enantioselectivity was achieved with ethanol rather than 2-propanol as the mobile phase modifier.

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Section: Chiral Recognition Of Novel Amylose Derivativesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

et al. 2017

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“…Envisaging, for polysaccharide derivatives, a novel function other than resolution of racemic mixtures , in this paper we show that HPLC coupled with polysaccharide‐based CSPs as XB acceptors (XBAs) can serve as analytical means for detection of weak stereoselective XBs in solution. Chiral halogenated 4,4′‐bipyridines lacking perfluorination were used as XBD test compounds.…”

Section: Introductionmentioning

confidence: 99%

Polysaccharide‐based chiral stationary phases as halogen bond acceptors: A novel strategy for detection of stereoselective σ‐hole bonds in solution

Peluso

Mamane

Dallocchio

et al. 2018

J of Separation Science

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In the last few years, halogen bonds have been exploited in a variety of research areas both in the solid state and in solution. Nevertheless, several factors make formation and detection of halogen bonds in solution challenging. Moreover, to date, few chiral molecules containing electrophilic halogens as recognition sites have been reported. Recently, we described the first series of halogen-bond-driven enantioseparations performed on cellulose tris(3,5-dimethylphenylcarbamate) by high-performance liquid chromatography. Herein the performances of amylose tris(3,5-dimethylphenylcarbamate) as halogen bond acceptor were also investigated and compared with respect to cellulose tris(3,5-dimethylphenylcarbamate). With the aim to explore the effect of polysaccharide backbone on the enantioseparations, the thermodynamic parameters governing the halogen-dependent enantioseparations on both cellulose and amylose polymers were determined by a study at variable temperature and compared. Molecular dynamics were performed to model the halogen bond in polysaccharide-analyte complexes. Chiral halogenated 4,4'-bipyridines were used as test compounds (halogen bond donors). On this basis, a practical method for detection of stereoselective halogen bonds in solution was developed, which is based on the unprecedented use of high-performance liquid chromatography as technical tool with polysaccharide polymers as molecular probes (halogen bond acceptors). The analytical strategy showed higher sensitivity for the detection of weak halogen bonds.

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“…HPLC is an effective technology for enantiomers separation. There are many materials for chiral HPLC, such as cellulose, cyclodextrin and MOF type chiral stationary phase (CSP) . At present, cellulose tris‐(3, 5‐dimethylphenylcarbamate) CSP is the most widely available and studied .…”

Section: Introductionmentioning

confidence: 99%

“…There are many materials for chiral HPLC, such as cellulose, cyclodextrin and MOF type chiral stationary phase (CSP). [16][17][18][19][20][21] At present, cellulose tris-(3, 5-dimethylphenylcarbamate) CSP is the most widely available and studied. [22][23][24] Such CSP is suitable for the resolution of enantiomers of different racemic compounds, such as stereochemistry and aromatic compounds.…”

Section: Introductionmentioning

confidence: 99%

Cellulose type chiral stationary phase based on reduced graphene oxide@silica gel for the enantiomer separation of chiral compounds

Zhu

et al. 2018

Chirality

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The graphene oxide (GO) was covalently coupled to the surfaces of silica gel (SiO ) microspheres by amide bond to get the graphene oxide@silica gel (GO@SiO ). Then, the GO@SiO was reduced with hydrazine to the reduced graphene oxide@silica gel (rGO@SiO ), and the cellulose derivatives were physically coated on the surfaces of rGO@SiO to prepare a chiral stationary phase (CSP) for high performance liquid chromatography. Under the optimum experimental conditions, eight benzene-enriched enantiomers were separated completely, and the resolution of trans-stilbene oxide perfectly reached 4.83. Compared with the blank column of non-bonded rGO, the separation performance is better on the new CSP, which is due to the existence of rGO to produce special retention interaction with analytes, such as π-π stacking, hydrophobic effect, π-π electron-donor-acceptor interaction, and hydrogen bonding. Therefore, the obtained CSP shows special selectivity for benzene-enriched enantiomers, improves separation selectivity and efficiency, and rGO plays a synergistic effect with cellulose derivatives on enantioseparation.

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Analytical and semipreparative chiral separation ofcis-itraconazole on cellulose stationary phases by high-performance liquid chromatography

Cited by 15 publications

References 31 publications

Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

Preparation and evaluation of regioselectively substituted amylose derivatives for chiral separations

Polysaccharide‐based chiral stationary phases as halogen bond acceptors: A novel strategy for detection of stereoselective σ‐hole bonds in solution

Cellulose type chiral stationary phase based on reduced graphene oxide@silica gel for the enantiomer separation of chiral compounds

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