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Chiral Separation (chiral + separation)
Selected AbstractsA Room Temperature Ionic Liquid (RTIL)-Mediated, Non-Hydrolytic Sol,Gel Methodology to Prepare Molecularly Imprinted, Silica-Based Hybrid Monoliths for Chiral Separation,ADVANCED MATERIALS, Issue 24 2006H.-F. Wang Silica-based hybrid molecularly imprinted polymer (MIP) monoliths with good chiral recognition ability are synthesized (see figure) using a novel method, a room temperature ionic liquid (RTIL)-mediated, non-hydrolytic sol,gel technique. The approach avoids the cracking and shrinking of the bed during drying, which is commonly associated with conventional sol,gel processing, overcomes the shortcomings associated with conventional organic-polymer-based MIP matrices, and offers improved selectivity. [source] Chiral Separation of Calcium (,)-2(S)-2-Benzyl-4-oxo-4-(cis -hexahydro-2-isoindolinyl)butyrate Enantiomers by High-performance Liquid Chromatography,CHINESE JOURNAL OF CHEMISTRY, Issue 1 2009Zhefeng ZHANG Abstract A chiral high-performance liquid chromatographic method was developed for the enantioseparation of a new insulinotropic drug of the glinide class with rapid onset. The chiral separation was performed on a Sumichiral OA-3300 column (250 mm×4.6 mm, 5 µm) with methanol containing 0.05 mol/L ammonium acetate as the optimized mobile phase at detection wavelengh 210 nm. Baseline separation of the two enantiomers was obtained in 22 min with a resolution of 3.01. Calibration graphs were constructed in a range of 0.028,5.6 µg·mL,1 for S - and 0.03,6.0 µg·mL,1 for R -(,)-enantiomer, respectively. The linear correlation equations are: y=1.32×103x,2.54 (r=0.9997) for S -enantiomer and y=1.15×103x,1.78 (r=0.9998) for R -enantiomer, respectively. The limits of detection obtained by S/N=3 were 0.15 ng for S - and 0.10 ng for R -enantiomer, respectively. RSD of the method was below 1.0% (n=5). [source] Recent Developments in Synthetic Chemistry, Chiral Separations, and Applications of Tröger's Base AnaloguesHELVETICA CHIMICA ACTA, Issue 3 2009Sergey Sergeyev Abstract Tröger's base is a well-known chiral molecule with a few unusual structural features. The chemistry of Tröger's base analogues has been greatly developed over the last 20 years, and numerous interesting applications in supramolecular chemistry and in molecular recognition have emerged. This Review gives a short overview of the chemistry of Tröger's base and its analogues, with particular focus on recent achievements in synthesis, enantiomer separations, and applications. [source] Editorial: Chromatographic Chiral SeparationsJOURNAL OF SEPARATION SCIENCE, JSS, Issue 10 2006Salvatore Fanali [source] Book Review: Chiral Separations , Methods and Protocols.JOURNAL OF SEPARATION SCIENCE, JSS, Issue 13 2004Edited by: Gerald Gübitz, Martin G. Schmid. [source] Chiral separation of dansyl amino acids by ligand exchange capillary electrochromatography in a low molecular weight organogel,ELECTROPHORESIS, Issue 18 2008Shaul Mizrahi Abstract Chiral electroseparation is demonstrated, for the first time, by a low molecular weight organogel filled capillary. Five pairs of dansylated amino acids were separated by copper ligand exchange on a trans -(1S,2S)-1,2-bis-(dodecylamido) cyclohexane (1) gel in methanol. Low molecular weight organogels are emerging materials that form stable, fibrillar, thermoreversible and thixotropic gels without covalent bonding of their monomeric building blocks. The dependence of chiral resolution and complex formation stability on the pH*, the ratio between copper and the D -valine selector, as well as other parameters were investigated revealing trends that were unparalleled in previously reports on copper ligand exchange of dansylated amino acids. These observations were explained in view of a simple stacking model of (1) and the difference in axial ligation of the amide carbonyl backbone of the gel to the dansyl D - or L -amino acid:D -valine:copper ternary complexes. [source] Chiral separation of the plant lignan matairesinol by capillary electrophoresis,ELECTROPHORESIS, Issue 17 2008Ulrike Müller Abstract Lignans are dimeric phenylpropanoid compounds in plants that enjoy increasing medicinal interest because of their phytoestrogen activity. Lignans are chiral compounds and for most natural occurring lignans, chirality is not known. Separation of racemic matairesinol by CE in a non-coated silica capillary with carboxymethyl-,-cyclodextrin as chiral selector in phosphate buffer was successful. Electrolyte and selector concentrations and pH were systematically optimized in order to obtain baseline separation and short analysis times. Matairesinol from safflower fruit was determined as (,)-enantiomer. Quantitation results for matairesinol with the optimized method after calibration with authentic lignan were very similar to those by HPLC. The limit of detection is 2,,g/mL sample by DAD detection. [source] Chiral separation of cetirizine by capillary electrophoresisELECTROPHORESIS, Issue 12 2006Ann Van Eeckhaut Abstract Chiral separation of cetirizine, a second-generation H1 -antagonist, was studied by CD-mediated CE. Several parameters, including pH, CD type, buffer concentration, type of co-ion, applied voltage and temperature, were investigated. The best conditions for chiral separation were obtained using a 75,mM triethanolamine-phosphate buffer (pH,2.5) containing 0.4,mg/mL heptakis(2,3-diacetyl-6-sulfato)-,-CD and 10%,ACN. Online UV detection was performed at 214,nm, a voltage of 20,kV was applied and the capillary was temperature controlled at 25°C by liquid cooling. Hydrodynamic injection was performed for 1,s. The method was validated for the quantification of levocetirizine in tablets and for enantiomeric purity testing of the drug substance. Selectivity, linearity, LOD and LOQ, precision and accuracy were evaluated for both methods. The amount of levocetirizine dihydrochloride in the commercially available tablets was quantified and was found to be within the specification limits of the claimed amount (5,mg). The amount of distomer in levocetirizine drug substance was found to be 0.87 ± 0.09%,w/w, which is in agreement with the certificate of analysis supplied by the company. [source] Chiral separation of N -imidazole derivatives, aromatase inhibitors, by cyclodextrin-capillary zone electrophoresis.ELECTROPHORESIS, Issue 16 2004Mechanism of enantioselective recognition Abstract Baseline separation of ten new, substituted [1-(imidazo-1-yl)-1-phenylmethyl)] benzothiazolinone and benzoxazolinone derivatives with one chiral center was achieved using cyclodextrin-capillary zone electrophoresis (CD-CZE). A method for the enantiomeric resolution of these compounds was developed using neutral CDs (native ,-, ,-, ,-CDs or ,-, ,-, ,-hydroxypropyl (HP)-CDs) as chiral selectors. Operational parameters including the nature and concentration of the chiral selectors, pH, ionic strength, organic modifiers, temperature, and applied voltage were investigated. The use of neutral CDs provides enantiomeric resolution by inclusion of compounds in the CD cavity. The HP-,-CD and HP-,-CD were found to be the most effective complexing agents and allowed efficient enantiomeric resolutions. Optimal separation of N -imidazole derivatives was obtained using 50 mM phosphate buffer at pH 2.5 containing either HP-,-CD or HP-,-CD (7.5,12.5 mM) at 25°C, with an applied field of 0.50 kV·cm,1 giving resolution factors Rs superior to 1.70 with migration times of the second enantiomer less than 13 min. The same enantiomer migration order observed for all molecules can be related to a close interaction mechanism with CDs. The influence of structural features of the solutes on Rs and tm was studied. The lipophilic character (log kw) of the solutes and the apparent and averaged association constants of inclusion complexes for four compounds with the six different CDs led us to rationalize the enantioseparation mechanisms. The conclusions were corroborated with reversed-phase high-performance liquid chromatography (HPLC) on chiral stationary phases (CSPs) based on CDs. [source] Enantioseparation of warfarin and its metabolites by capillary zone electrophoresisELECTROPHORESIS, Issue 15 2003Qingyu Zhou Abstract A capillary zone electrophoresis (CZE) method with direct ultraviolet (UV)-absorbance detection is presented for the simultaneous enantiomeric separation of warfarin and its main metabolites, including warfarin alcohols, 4'-, 6-, and 7-hydroxywarfarin, using highly sulfated ,-cyclodextrin (HS-,-CD) as the chiral selector. This chiral separation method was optimized in terms of the electrophoretic parameters, which included the concentration of HS-,-CD used, the type and composition of organic modifier added to the background electrolyte (BGE) buffer, and the BGE buffer pH. Chiral separation of warfarin and its major metabolites was achieved with high resolution, selectivity, efficiency, repeatability, and reproducibility. This optimized chiral analysis of warfarin along with its metabolites was completed within a satisfactory electrophoresis time of 20 min. [source] High-performance liquid chromatographic resolution of 1-(1,4-benzodioxane-2-formyl)- piperazine enantiomers after chiral derivatizationJOURNAL OF SEPARATION SCIENCE, JSS, Issue 2 2005Zhiqiong Chen Abstract Chiral separation of racemic mixtures is of the greatest importance to the pharmaceutical industry, as the isomers of a given racemate may exhibit substantially different pharmacological effects, not to mention possibly differing toxicity behaviour. A novel chiral separation method is developed for the determination of 1-(1,4-benzodioxane-2-formyl)piperazine (BFP) enantiomers. The indirect resolution is performed by applying precolumn derivatization with the chiral reagent 2,3,4,6-tetra- O -acetyl-,-D-glucopyranosyl isothiocyanate (GITC). The resulting diastereoisomers are separated on a reversed-phase ODS column with methanol-potassium dihydrogen phosphate (0.02mol/L, 50:50) as mobile phase. UV detection is at 250 nm. The effect of mobile phase composition upon resolution and analysis time is investigated. Two diastereoisomers show nearly base-line separation under optimal chromatographic conditions. The presented study provides a simple and accurate method for the enantiomeric quality control and the optical purity assay of BFP. [source] Chiral separation of omeprazole and several related benzimidazoles using supercritical fluid chromatographyJOURNAL OF SEPARATION SCIENCE, JSS, Issue 12 2004M. Jesús del Nozal Abstract A study of the enantiomeric separation of omeprazole and several related benzimidazoles, using supercritical fluid chromatography (SFC), on the amylose based column Chiralpak AD is presented in this work. The effect of the organic modifier as well as temperature on the retention and enantioresolution was investigated. Alcohol-type modifiers provided the best results, allowing the enantiomeric separation of all the compounds studied with resolutions that were in most cases higher than 2, and analysis times lower than 10 minutes. An investigation of the temperature effect revealed that the isoelution temperature was below the working temperature range in only two cases, and hence it was better to work at the highest temperature permitted. [source] Chiral separation of the ,2 -sympathomimetic fenoterol by HPLC and capillary zone electrophoresis for pharmacokinetic studiesBIOMEDICAL CHROMATOGRAPHY, Issue 10 2010Thomas Ullrich Abstract The development of methods for the separation of the enantiomers of fenoterol by chiral HPLC and capillary zone electrophoresis (CZE) is described. For the HPLC separation precolumn fluorescence derivatization with naphthyl isocyanate was applied. The resulting urea derivatives were resolved on a cellulose tris(3,5-dimethylphenylcarbamate)-coated silica gel column employing a column switching procedure. Detection was carried out fluorimetrically with a detection limit in the low ng/mL range. The method was adapted to the determination of fenoterol enantiomers in rat heart perfusates using liquid,liquid extraction. As an alternative a CE method was used for the direct separation of fenoterol enantiomers comparing different cyclodextrin derivatives as chiral selectors. Copyright © 2010 John Wiley & Sons, Ltd. [source] Chiral separation of rac -Ornidazole and detection of the impurity of (R)-Ornidazole in (S)-Ornidazole injection and raw materialCHIRALITY, Issue 8 2006Jianquan Huang Abstract (S)-Ornidazole is a subject of research as an antifertility agent in male animals at present. However, there seems to be no relative report on chiral separation for rac -Ornidazole, which has been used as an effective medicine for more than 30 years. In this article, the chiral separation of rac -Ornidazole on a Chiralcel OB-H column based on normal-phase high-performance liquid chromatography (NP-HPLC) is investigated and the methodology for detection of impurity of (R)-Ornidazole in (S)-Ornidazole injection and raw material is established. The novel mobile phase is utilized by mixing n -hexane, methanol and isopropyl alcohol (95:4:1, v/v/v) instead of the typical mobile phase of n -hexane and isopropyl alcohol, although the methanol, which offers a good resolution factor for the enantiomeric separation in this system, is not recommended on the Chiralcel OB-H column according to the instruction supplied by Daicel Chemical Ind., LTD (Japan). Chirality, 2006. © 2006 Wiley-Liss, Inc. [source] Chiral separation and CD characterisation of enantiomeric cyclotriphosphazene derivativesCHIRALITY, Issue 8 2005Tam T.T. Bui Abstract The gem-disubstituted cyclotriphosphazene 1 reacted with piperazine (pip) to give the piperazine-bridged derivative 2, which is expected to exist in meso and racemic forms because the two PCl (pip) groups are stereogenic. The proton-decoupled 31P NMR spectrum of 2 gave rise to two similar sets of ABX signals in a 1:1 ratio, consistent with formation of diastereoisomers. The meso and racemic forms of compound 2 were separated by column chromatography on silica gel and characterised by elemental analysis, mass spectrometry, 31P NMR spectroscopy, and X-ray crystallography. Using HPLC with a chiral stationary phase, the racemic form of compound 2 was further separated into enantiomers, which were characterised by circular dichroism (CD) spectroscopy. This is the first report of the separation of enantiomers in the field of cyclophosphazene chemistry and hence the first CD spectra of derivatives in which the cyclophosphazene ring is at the chiral centre. © 2005 Wiley-Liss, Inc. Chirality 17:438,443, 2005. [source] Polymeric alkenoxy amino acid surfactants: II.,Chiral separations of ,-blockers with multiple stereogenic centersELECTROPHORESIS, Issue 6 2004Syed A. A. Rizvi Abstract Two amino acid-based (leucine and isoleucine) alkenoxy micelle polymers were employed in this study for the separation of multichiral center-bearing ,-blockers, nadolol and labetalol. These polymers include polysodium N -undecenoxy carbonyl- L -leucinate (poly- L -SUCL) and polysodium N -undecenoxy carbonyl- L -isoleucinate (poly- L -SUCIL). Detailed synthesis and characterization were reported in our previous paper [26]. It was found that poly- L -SUCIL gives better chiral separation than poly- L -SUCL for both nadolol and labetalol isomers. The use of 50,100 mM poly- L -SUCIL as a single chiral selector provided separation of four and three isomers of labetalol and nadolol, respectively. Further optimization in separation of both enantiomeric pairs of nadolol and labetalol was achieved by evaluation of type and concentration of organic solvents, capillary temperature as well type and concentration of cyclodextrins. A synergistic approach, using a combination of poly- L -SUCIL and sulfated ,-CD (S-,-CD) was evaluated and it showed dramatic separation for enantiomeric pairs of nadolol. On the other hand for labetalol enantiomers, separation was slightly decreased or remain unaffected using the dual chiral selector system. Finally, simultaneous separation of both nadolol and labetalol enantiomers was achieved in a single run using 25 mM poly- L -SUCIL and 5% w/v of S-,-CD in less then 35 min highlighting the importance of high-throughput chiral analysis. [source] Chiral separations on polysaccharide stationary phases using polar organic mobile phasesCHIRALITY, Issue 1 2006Kenneth G. Lynam Abstract About 30% of a chemically diverse set of compounds were found to separate on four polysaccharide chiral stationary phases using polar organic mobile phases. No structural features appeared to correlate to successful separations. Titrations between normal and polar organic mobile phases suggested that separation mechanisms do not differ between these mobile phases. Attempts made to control retention met with varying degrees of success. Addition of hexane to alcohols had minor effects on retention although this was occasionally beneficial. Addition of water to alcohols increased retention. Addition of water to acetonitrile decreased retention. Addition of alcohol to acetonitrile also proved beneficial to the separation of some compounds. Loading studies performed to mimic preparative separations indicated that the benefits of polar organic mobile phases are largely due to increased solubility. © 2005 Wiley-Liss, Inc. Chirality [source] Separation of amino alcohols using divalent dipeptides as counter ions in aqueous CEELECTROPHORESIS, Issue 10 2010Jakob Haglöf Abstract Divalent dipeptides have been introduced as counter ions in aqueous CZE. The dipeptides form ion pairs with amino alcohols in the BGE and facilitate the separation of amino alcohols. High concentrations of dipeptide caused reversed effective mobility for the analytes. The net charge of the dipeptide can be controlled using a buffer or a strong base, and regulates the interaction between the dipeptide and the amino alcohol. A stronger interaction and higher selectivity of amino alcohols was observed when the dipeptides were used as divalent counter ions, than in monovalent or uncharged form. Association constants for ion pairs between divalent dipeptides and amino alcohols can be used to enhance selectivity for amino alcohols in CZE. No chiral separation of amino alcohols was observed when using the dipeptides as ion-pairing chiral selectors in aqueous BGE, but addition of methanol to the BGE promoted enantioselectivity. [source] Heart-cutting 2D-CE with on-line preconcentration for the chiral analysis of native amino acidsELECTROPHORESIS, Issue 6 2010Suzanne Anouti Abstract The use of transient moving chemical reaction boundary (tMCRB) was investigated for the on-line preconcentration of native amino acids in heart-cutting 2D-CE with multiple detection points using contactless conductivity detection. The tMCRB focusing was obtained by using ammonium formate (pH 8.56) as sample matrix and acetic acid (pH 2.3) as a BGE in the first dimension of the heart-cutting 2D-CE. Different experimental parameters such as the injected volume and the concentration in ammonium formate were optimized for improving the sensitivity of detection. A stacked fraction from the first dimension was selected, isolated in the capillary, and then separated in the second dimension in the presence of a chiral selector ((+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid). This on-line tMCRB preconcentration coupled with heart-cutting 2D-CE was applied with success to the chiral separation of D,L -phenylalanine, and D,L -threonine in a mixture of 22 native amino acids. The sample mixture was diluted in 0.8,M of ammonium formate, and injected at a concentration of 2.5,,M for each enantiomer with a volume corresponding to 10% of the total capillary volume. An LOD (S/N=3) of 2,,M was determined for L -threonine. [source] Cellulose dimethylphenylcarbamate-immobilized zirconia for chiral separation in reversed-phase CECELECTROPHORESIS, Issue 22 2009Jurim Gwon Abstract Cellulose dimethylphenylcarbamate (CDMPC)-immobilized zirconia (CDMPCZ) was used as a chiral stationary phase for enantioseparation of a set of nine racemic compounds in reversed-phase CEC. Influences of the type and composition of organic modifier and the applied voltage on enantioseparation were examined. Separation data on CDMPCZ were also compared with those on CDMPC-immobilized silica (CDMPCS). Enantiomers of the analytes investigated are well separated in ACN/phosphate buffer mobile phases. Better enantioselectivity and resolution were obtained with ACN than MeOH as the organic modifier. Retention was longer but better enantioselectivity and resolution were obtained on CDMPCZ than CDMPCS. [source] The effect of co-surfactant-modified micelles on chiral separations in EKCELECTROPHORESIS, Issue 16 2009Adeline B. Kojtari Abstract The use of chiral pseudostationary phases in EKC provides high efficiencies and excellent resolution for enantiomeric separations. The chiral pseudostationary phases of interest in this study are alcohol-modified ("swollen") micelles, in which a co-surfactant (medium chain-length alcohol) is added with the surfactant. In this study, the chiral surfactant, dodecoxycarbonylvaline (DDCV), along with the co-surfactant, 2-hexanol, has been prepared as swollen micelle in order to investigate the chiral separation of enantiomeric pairs. Three sets of experiments were investigated in which swollen micelle systems contained: chiral surfactant and racemic co-surfactant; chiral surfactant and chiral co-surfactant; and phase ratio increases, in which both chiral surfactant and chiral co-surfactant were employed. In the first two sets of experiments, co-surfactant concentration was held constant and the surfactant concentration was increased. In the third set of experiments, both surfactant and chiral surfactant concentrations were increased proportionally. The chromatographic figures of merit for each enantiomeric pair were investigated and compared with various chiral aggregate systems. In swollen micelle compositions using constant racemic 2-hexanol concentration, when DDCV concentration increased, enantioselectivity and resolution increased; whereas, efficiency remained constant for most of the test compounds. Compositions using constant S -2-hexanol concentration reached a maximum in all chromatographic figures of merit when DDCV concentration was increased from 2 to 3%. An increase in both surfactant and co-surfactant concentrations led to noisy baselines and chiral aggregates that were generally unstable in solution. [source] On-line preconcentration and enantioseparation of thalidomide racemates by CEC with the hyphenation of octyl and norvancomycin monolithsELECTROPHORESIS, Issue 4 2009An-Na Tang Abstract A method was developed for simultaneous preconcentration and chiral separation of thalidomide enantiomers in human urine by CEC in combination with self-concentration and solvent gradient effects. A 4,cm long octyl (C8) monolithic column was hyphenated with a 15,cm long norvancomycin (NVC)-bonded monolithic column via a fluorinated ethylene,propylene interface. Sample solution was injected into the C8 monolithic column, the two thalidomide enantiomers were first preconcentrated on the C8 monolithic column, and then separated with a further concentration on the NVC-bonded monolithic column by CEC. Injection of 34.8,mm plug of sample solution gave 278- and 298-fold enhancement in sensitivity, and detection limits of 90 and 94,,g/L for the two thalidomide enantiomers. Peak areas of the two isomers were linear in a range of 0.5,50,mg/L. The precision for five replicate injections of 10,mg/L were 0.8,0.9 and 1.1,2.3% for the migration time and peak height, respectively. The developed method was applied to the determination of racemic thalidomide in spiked human urine samples. [source] Electrokinetic partial filling technique as a powerful tool for enantiomeric separation of DL -lactic acid by CE with contactless conductivity detectionELECTROPHORESIS, Issue 11 2007zslav Maier Dr. Abstract A modified partial filling method for chiral separation of DL -lactic acid as the model chiral compound with vancomycin chloride as the chiral selector was developed by CE with contactless conductivity detection. Electrokinetic partial filling technique (EK-PFT) was used as an alternative method to the conventional hydrodynamic partial filling method. EK-PFT, in contrast to the hydrodynamic partial filling technique, allowed the removal of the chloride counterions from the chiral selector which otherwise led to poor sensitivity in conductivity detection. The baseline separation of DL -lactic acid as the model analyte was achieved in 5,min in a polyacrylamide-coated capillary. The best resolution was achieved by electrokinetic partial filling of vancomycin cations from the injection solution containing 5,mmol/L oxalate L -histidinium at pH,4.5 with 10,mmol/L vancomycin chloride. Computer simulation was used to explain the observed phenomena in the boundary between the inject vial and the capillary during the EK-PFT of vancomycin cations. [source] Advances in chiral separation using capillary electromigration techniquesELECTROPHORESIS, Issue 1-2 2007Gerald Gübitz Professor Abstract This review gives an overview of recent develoments in CZE, EKC, and CEC covering the literature since the year 2004. Since there appeared a special issue on applications, this review focuses on the progress in electromigration techniques and new methodological developments. New techniques, new chiral selectors as well as new chiral stationary phases for CEC are discussed. [source] Effect of alkali metal hydroxides on the enantioseparation of amines using di- O -isopropylidene-keto- L -gulonic acid as the selector in NACEELECTROPHORESIS, Issue 22 2006Ylva Hedeland Dr. Abstract The present work demonstrates the importance of the ionic composition in the BGE for enantioseparation. (,)-2,3:4,6-di- O -Isopropylidene-2-keto- L -gulonic acid ((,)-DIKGA) has been used as the chiral selector in methanolic and ethanolic BGEs. The influence of added alkali metal hydroxides on the EOF and the chiral separation of amines (atenolol, isoprenaline, pindolol and propranolol) have been studied. The ion-pair formation constants in ethanol were determined by precision conductometry for the enantiomers of pindolol with (,)-DIKGA, for Li+, Na+ and Cs+ with (,)-DIKGA, and also for the corresponding alkali metal hydroxides. The effective mobilities and the enantiomeric mobility differences were affected by the type of alkali metal hydroxide (LiOH, NaOH, KOH, RbOH or CsOH) added to the BGE. The effective mobility and mobility difference were increased with decrease in solvated radius of the alkali metal cation. These differences could partly be correlated to the ion-pair formation constants of the alkali metal cations with the chiral selector, affecting the equilibrium concentration of the free selector. The electroosmosis was also affected by the alkali metal hydroxide added to the BGE. The cathodic electroosmosis decreased with decreasing solvated radius of the alkali metal cation added to the BGE. Interestingly, the cathodic EOF was even reversed, i.e. became anodic in the ethanolic BGEs containing KOH, RbOH or CsOH and the methanolic ones with RbOH and CsOH. [source] Chiral separation of cetirizine by capillary electrophoresisELECTROPHORESIS, Issue 12 2006Ann Van Eeckhaut Abstract Chiral separation of cetirizine, a second-generation H1 -antagonist, was studied by CD-mediated CE. Several parameters, including pH, CD type, buffer concentration, type of co-ion, applied voltage and temperature, were investigated. The best conditions for chiral separation were obtained using a 75,mM triethanolamine-phosphate buffer (pH,2.5) containing 0.4,mg/mL heptakis(2,3-diacetyl-6-sulfato)-,-CD and 10%,ACN. Online UV detection was performed at 214,nm, a voltage of 20,kV was applied and the capillary was temperature controlled at 25°C by liquid cooling. Hydrodynamic injection was performed for 1,s. The method was validated for the quantification of levocetirizine in tablets and for enantiomeric purity testing of the drug substance. Selectivity, linearity, LOD and LOQ, precision and accuracy were evaluated for both methods. The amount of levocetirizine dihydrochloride in the commercially available tablets was quantified and was found to be within the specification limits of the claimed amount (5,mg). The amount of distomer in levocetirizine drug substance was found to be 0.87 ± 0.09%,w/w, which is in agreement with the certificate of analysis supplied by the company. [source] Capillary electrophoresis using copolymers of different composition as physical coatings: A comparative studyELECTROPHORESIS, Issue 5-6 2006Guillaume L. Erny Abstract In this work, a comparative study on the use of different polymers as physically adsorbed coatings for CE is presented. It is demonstrated that the use of ad hoc synthesized polymers as coatings allows tailoring the EOF in CE increasing the flexibility of this analytical technique. Namely, different polymers were synthesized at our laboratory using different percentages of ethylpyrrolidine methacrylate (EpyM) and N,N -dimethylacrylamide (DMA). Thus, by modifying the percentage of EpyM and DMA monomers it is possible to manipulate the positive charge of the copolymer, varying the global electrical charge on the capillary wall and with that the EOF. These coated capillaries are obtained by simply flushing a given EpyM,DMA aqueous solution into bare silica capillaries. It is shown that by using these coated capillaries at adequate pHs, faster or more resolved CE separations can be achieved depending on the requirements of each analysis. Moreover, it is demonstrated that these coated capillaries reduce the electrostatic adsorption of basic proteins onto the capillary wall. Furthermore, EpyM,DMA coatings allow the reproducible chiral separation of enantiomers through the partial filling technique (PFT). The EpyM,DMA coated capillaries are demonstrated to provide reproducible EOF values independently of the pH and polymer composition with%RSD values lower than 2% for the same day. It is also demonstrated that the coating procedure is reproducible between capillaries. The compatibility of this coating protocol with CE in microchips is discussed. [source] Capillary electrophoretic chiral separation of hydroxychloroquine and its metabolites in the microsomal fraction of liver homogenatesELECTROPHORESIS, Issue 5-6 2006Carmem Dickow Cardoso Abstract A rapid, selective, and low-cost chiral capillary electrophoretic method was developed for the simultaneous analysis of hydroxychloroquine (HCQ) and its three chiral metabolites: desethylchloroquine (DCQ), desethylhydroxychloroquine (DHCQ), and bisdesethylchloroquine (BDCQ) in the microsomal fraction of liver homogenates. After liquid,liquid extraction using toluene as extracting solvent, the drug and metabolites were resolved on a fused-silica capillary (50,,m ID, 50,cm total length, and 42,cm effective length), using 100,mmol/L of Tris/phosphate buffer, pH,9.0 containing 1% w/v sulfated-,-CD and 30,mg/mL hydroxypropyl-,-CD. Detection was carried out at 220,nm. The extraction procedure was efficient in removing endogenous interferents, and low values (,15%) for CVs and deviation from theoretical values were demonstrated for both within-day and between-day assays. The quantitation limit was 125,ng/mL with linear response over the 125,2000,ng/mL of concentration range for all metabolites. After validation, the method was used for an in vitro metabolism study of HCQ. The major HCQ metabolite formed by microsomal enzymes was (,)-(R)-DHCQ. [source] Polymeric alkenoxy amino acid surfactants: II.,Chiral separations of ,-blockers with multiple stereogenic centersELECTROPHORESIS, Issue 6 2004Syed A. A. Rizvi Abstract Two amino acid-based (leucine and isoleucine) alkenoxy micelle polymers were employed in this study for the separation of multichiral center-bearing ,-blockers, nadolol and labetalol. These polymers include polysodium N -undecenoxy carbonyl- L -leucinate (poly- L -SUCL) and polysodium N -undecenoxy carbonyl- L -isoleucinate (poly- L -SUCIL). Detailed synthesis and characterization were reported in our previous paper [26]. It was found that poly- L -SUCIL gives better chiral separation than poly- L -SUCL for both nadolol and labetalol isomers. The use of 50,100 mM poly- L -SUCIL as a single chiral selector provided separation of four and three isomers of labetalol and nadolol, respectively. Further optimization in separation of both enantiomeric pairs of nadolol and labetalol was achieved by evaluation of type and concentration of organic solvents, capillary temperature as well type and concentration of cyclodextrins. A synergistic approach, using a combination of poly- L -SUCIL and sulfated ,-CD (S-,-CD) was evaluated and it showed dramatic separation for enantiomeric pairs of nadolol. On the other hand for labetalol enantiomers, separation was slightly decreased or remain unaffected using the dual chiral selector system. Finally, simultaneous separation of both nadolol and labetalol enantiomers was achieved in a single run using 25 mM poly- L -SUCIL and 5% w/v of S-,-CD in less then 35 min highlighting the importance of high-throughput chiral analysis. [source] Role of the charge in continuous beds in the chiral separation of hydroxy acids by ligand-exchange capillary electrochromatographyELECTROPHORESIS, Issue 17 2003Oliver Lecnik Abstract This paper deals with the chiral separation of hydroxy acids using diallyl-dimethylammonium chloride as a positive charge-providing agent in the continuous bed. The chiral continuous bed was prepared by in situ copolymerization of monomers, including an L -4-hydroxyproline derivative as a chiral selector. This phase was applied to the chiral separation of hydroxy monocarboxylic acids and hydroxy dicarboxylic acids, respectively. The influence of both the selector concentration and the charge-providing agent on retention and separation was investigated. [source] | |||||||||||||