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Enantioseparations of liquid crystalline materials
Vaňkátová, Petra ; Kubíčková, Anna (advisor) ; Čabala, Radomír (referee) ; Kohout, Michal (referee)
(EN) Liquid crystalline materials are an important domain of the material science. Chiral liquid crystals (CLCs) are researched for their unique chirality-derived properties. The development of new CLCs focuses both on appropriate molecular design to fit their intended purpose and also on ways of using widely available and less expensive sources of chirality to enable cost- effective production for a potential large-scale production. Methods capable of enantioseparation are needed mainly for chiral purity control of newly synthesized CLCs and for their potential use in scaling up for preparative purpose. Nowadays, enantioselective chromatography has evolved to be the method of choice for enantioseparations. This thesis aims to establish new approaches to chromatographic enantioseparations of CLCs by developing fast and robust enantioselective methods using two different ultra-high performance chromatographic techniques - sub/supercritical fluid chromatography (UHPSFC) and liquid chromatography (UHPLC). UHPSFC is introduced and successfully employed for the first time for this purpose. For some CLCs, high values of enantioselectivity and enantioresolution were achieved, opening the possibility of scaling up to semipreparative use. In UHPLC, two modes (reversed-phase and polar organic solvent mode)...
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Chiral separation of biologically active compounds by chromatography
Landl, David ; Kalíková, Květa (advisor) ; Kubíčková, Anna (referee)
- 4 - Abstract in English This diploma thesis is focused on the evaluation and comparison of the enantioselective potential of two columns CHIRAL ART Amylose-SA and CDShell-RSP using a set of 29 chiral drugs in high performance liquid chromatography. The separations of enantiomers were performed in three modes: reversed-phase, normal-phase, and polar- organic mode. The CHIRAL ART Amylose-SA column was tested in normal-phase mode, the CDShell-RSP column in reversed-phase and polar-organic modes. The CHIRAL ART Amylose-SA column contains amylose tris(3,5- dimethylphenylcarbamate) immobilized on 3 µm porous silica gel particles. The CDShell-RSP column contains a chiral selector hydroxypropyl-β-cyclodextrin, which is covalently bonded on 2.7 µm superficially porous particles. In the normal-phase mode, mobile phases composed of hexane and propane-2-ol were used. Furthermore, the effect of various additives (triethylamine, diethylamine, trifluoroacetic acid, and the mixture of diethylamine and trifluoroacetic acid) in the mobile phase on the enantioseparation of chiral drugs was tested. The most universal additive was a mixture of diethylamine and trifluoroacetic acid. A total of 22 chiral drugs were enantioseparated on the CHIRAL ART Amylose-SA column, 10 of them were baseline separated. Mobile phases for...
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Separation of chiral compounds
Šrolerová, Tereza ; Kubíčková, Anna (advisor) ; Křížek, Tomáš (referee)
This bachelor thesis deals with the chiral separation of newly synthesized orthoconic antiferroelectric liquid crystals using ultra-high performance liquid chromatography. These studied compounds differ in the alkyloxy-spacer length, in the presence and/or position of the fluorine atom on the phenyl ring and in the chiral center. The separation took place in a reverse separation mode using a chiral stationary phase based on derivatized amylose. First, the effect of mobile phase flow rate and column temperature on separation efficiency was exanimated. The effect of the composition of the mobile phase on the enantioseparation were studied at the optimum temperature and flow rate. The mobile phase was based on acetonitril, while deionized water was added gradually using isocratic elution. Furthermore, the effect of chromatographic conditions and the structure of the studied analytes on resolution and enantioselectivity was investigated, concretely the presence and position of fluorine atom on pfenyl ring, the length of alkyloxy-spacer and the effect of divergent chiral center. Under optimized chromatography conditions we succeeded to separate all examined substances on the base line. Key words: ultra-high performance chromatography, liquid crystals, enantioseparation, chiral stationary phase, reverse mode
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Chiral separation of biologically active compounds by chromatography
Landl, David ; Kalíková, Květa (advisor) ; Kubíčková, Anna (referee)
- 4 - Abstract in English This diploma thesis is focused on the evaluation and comparison of the enantioselective potential of two columns CHIRAL ART Amylose-SA and CDShell-RSP using a set of 29 chiral drugs in high performance liquid chromatography. The separations of enantiomers were performed in three modes: reversed-phase, normal-phase, and polar- organic mode. The CHIRAL ART Amylose-SA column was tested in normal-phase mode, the CDShell-RSP column in reversed-phase and polar-organic modes. The CHIRAL ART Amylose-SA column contains amylose tris(3,5- dimethylphenylcarbamate) immobilized on 3 µm porous silica gel particles. The CDShell-RSP column contains a chiral selector hydroxypropyl-β-cyclodextrin, which is covalently bonded on 2.7 µm superficially porous particles. In the normal-phase mode, mobile phases composed of hexane and propane-2-ol were used. Furthermore, the effect of various additives (triethylamine, diethylamine, trifluoroacetic acid, and the mixture of diethylamine and trifluoroacetic acid) in the mobile phase on the enantioseparation of chiral drugs was tested. The most universal additive was a mixture of diethylamine and trifluoroacetic acid. A total of 22 chiral drugs were enantioseparated on the CHIRAL ART Amylose-SA column, 10 of them were baseline separated. Mobile phases for...
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Enantioselective potential of sulfobutylether-β-cyclodextrin based chiral stationary phase
Folprechtová, Denisa ; Kalíková, Květa (advisor) ; Kubíčková, Anna (referee)
The aim of this diploma thesis was to prepare two new chiral stationary phases by dynamic coating of sulphobutylether-β-cyclodextrin (SBE-β-CD) with varying degrees of substitution onto strong anion-exchange stationary phases. The enantioselective potential and stability of the newly prepared chiral stationary phases were tested using a set of chiral analytes. The set contained structurally diverse analytes, i.e. benzodiazepines (oxazepam, lorazepam), phenothiazines (thioridazine, promethazine), β-blockers (labetalol, pindolol, propranolol, alprenolol), profens (carprofen, fenoprofen, flurbiprofen, indoprofen), flavanones (6-hydroxyflavanone, 7-hydroxyflavanone), DL-tryptophan and its derivatives (5-OH-DL-tryptophan, 5-F-DL-tryptophan, DL-tryptophan butylester and blocked aminoacid (t-Boc-DL-tryptophan)), dipeptides (glycyl-DL-phenylalanine, glycyl-DL-tryptophan) and Troger's base. Measurements were carried out in reversed-phase high-performance liquid chromatography. Mobile phases consisted of methanol/formic acid (pH 2.10) and methanol/10mmol l-1 ammonium acetate buffer (pH 4.00) in various volume ratios. The chiral stationary phase containing hexasubstituted SBE-β-CD was suitable for enantioseparation of eleven analytes. Four of them were baseline enantioresolved and seven partially. The chiral...
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Enantioselective separation of certain analytes using supercritical fluid chromatography and high performance liquid chromatography
Martínková, Monika ; Tesařová, Eva (advisor) ; Čabala, Radomír (referee)
(EN) Cellulose tris-(3,5-dimethylphenylcarbamate) chiral stationary phase was used for separation of selected 24 analytes. Enantioseparations were realized using two systems, high performance liquid chromatography and supercritical fluid chromatography. Effect of mobile phase composition was studied. Five different aditives (isopropylamine, diethylamine, triethylamine, trifluoroacetic acid, isopropylamine combined with trifluoroacetic acid) and their influence on enantioseparation were tested. Influence of two different modifiers (methanol, propan-2-ol) combined with all aditives was also tested in supercritical fluid chromatography system. The aim of this work was to find optimized composition of mobile phase which was suitable for separation of the analytes studied and to compare separation potential among all mobile phases and also between used separations systems. The supercritical fluid chromatography was shown to yield better results, i.e. better resolution in shorter analysis time. However examples of analytes better resolved under optimized conditions in high performance liquid chromatography system have also been found. Keywords (EN) Chirality, enantiomers, enantioselective separation, chiral stationary phase, high performance liquid chromatography, supercritical fluid chromatography.
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