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Chiralpak AD (chiralpak + ad)
Selected AbstractsSeparation and aquatic toxicity of enantiomers of the pyrethroid insecticide lambda-cyhalothrin,ENVIRONMENTAL TOXICOLOGY & CHEMISTRY, Issue 1 2008Chao Xu Abstract Chiral pollutants are receiving growing environmental concern due to differential biological activities of their enantio-mers. In the present study, enantiomeric separation of the pyrethroid insecticide lambda-cyhalothrin (LCT) was investigated by high-performance liquid chromatography (HPLC) using the columns of Chiralpak AD (amylase tris[3,5-dimethyl-phenylcarbamate]), Chiralpak AS (amylase tris[(S)-1-phenyl carbamate]), Chiralcel OD (cellulose tris[3,5-dimethylphenyl carbamate]), and Chiralcel OJ (cellulose tris[4-methyl benzoate]) with different chiral stationary phases. The differential toxicities of the enantiomers in aquatic systems were evaluated using the acute zebrafish (Danio rerio) toxicity test and the zebrafish embryo test. The enantiomers of LCT were separated completely on all the columns tested and detected by circular dichroism at 236 nm. Better separations were achieved at lower temperatures (e.g., 20°C) and lower levels of polar modifiers (,5%) in mobile phase. Ethanol was found to be a good modifier of the mobile phase for all the columns, although isopropanol acted better for the Chiralcel OD column. The (,)-enantiomer was >162 times more toxic than its antipode to zebrafish in the acute test. The embryo test indicated that the exposure to LCT enantioselectively induced crooked body, yolk sac edema, and pericardial edema and that the (,)-enantiomer was 7.2 times stronger than the (+)-enantiomer in 96-h mortality. The malformations were induced by the racemate and its (,)-enantiomer at lower concentrations tested (e.g., 50 ,g L,1), whereas the (+)-enantiomer induced malformations at relatively higher concentrations (,100 ,g L,1). These results suggest that the toxicological effects of chiral pesticides must be evaluated using their individual enantiomers. [source] Separation of chiral mixtures in real SMB units: The FlexSMB-LSRE®AICHE JOURNAL, Issue 1 2010Pedro Sá Gomes Abstract In this work, a procedure for the separation of a racemic mixture of guaifenesin onto a chiral stationary phase (Chiralpak AD), by means of Simulated Moving Bed (SMB) technology, is presented in four major steps: (1) search for the suitable stationary and mobile phases; (2) determination of sorption parameters and validation by frontal analysis; (3) modeling and design of the SMB unit; and (4) operation and demonstration. A major emphasis is given to the common deviations that "real" SMB units present when compared with the theoretical apparatus (due to tubing and equipment dead volumes, switching time asymmetries and delays, pumps flow rates variations). These deviations are analyzed before and after the design and construction of the FlexSMB-LSRE® unit, a new flexible unit, hereby presented. A detailed model that takes into account tubing and equipment dead volumes, as well as switching time asymmetries and delay, was used to study and compare different dead volumes design and compensating strategies. It is shown that all these approaches can be converged into a switching time compensating strategy. This approach served to predict the experimental operating conditions and run a classical SMB experiment, which afterwards was compared with the simulated profiles obtained for the FlexSMB-LSRE® unit. The result of the separation was guaifenesin enantiomers with purities above 98% and a productivity value of 23 genantiomer/(dm3 CSP day). © 2009 American Institute of Chemical Engineers AIChE J, 2010 [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] Column selection and method development for the separation of nucleoside phosphotriester diastereoisomers, new potential anti-viral drugs.BIOMEDICAL CHROMATOGRAPHY, Issue 6 2005Application to cellular extract analysis Abstract Analytical HPLC methods using derivatized cellulose and amylose chiral stationary phases used in normal and reversed-phase modes were developed for the diastereoisomeric separation of mononucleotide prodrugs (pronucleotides) of 3,-azido-2,,3,-dideoxythymidine (AZT). The resolutions were performed with two silica-based celluloses using normal and reversed-phase methodologies: Tris-3,5-dimethylphenylcarbamate (Chiralcel OD-H and Chiracel OD-RH) and Tris-methylbenzoate (Chiralcel OJ and OJ-R). Two amyloses phases, Tris-3,5-dimethylphenylcarbamate (Chiralpak AD) and Tris-(S)-1-phenylethylcarbamate (Chiralpak AS), were used in normal-phase mode. Additionally, we developed separation using two stationary phases with immobilized cyclodextrins in reversed-phase and polar-organic modes. The mobile phase and the chiral stationary phase were varied to achieve the best resolution. Different types and concentration of aliphatic alcohols, acetonitrile or water in the mobile phase were also tested for the different separation modes. An optimal baseline separation (Rs > 1.5) was readily obtained with all silica-based celluloses and amyloses using a normal-phase methodology. The different columns gave complementary results in term of resolution. Limits of detection and quantification were 0.12,0.20 and 0.40,0.67 µm, respectively. This analytical method was applied in a preliminary study for the pronucleotide 2 quantification in cellular extract. Copyright © 2005 John Wiley & Sons, Ltd. [source] Direct high-performance liquid chromatographic separation of the enantiomers of venlafaxine and 11 analogs using amylose-derived chiral stationary phasesCHIRALITY, Issue 6 2009Salvatore Caccamese Abstract A direct liquid chromatographic enantioselective separation of venlafaxine and 11 analogs was obtained in the normal phase mode using Chiralpak AD. For some compounds, a comparison between the enantioseparation using coated and immobilized amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phases (Chiralpak AD and Chiralpak IA, respectively) was made. The best separations were achieved on Chiralpak AD with ethanol as alcoholic modifier in a mobile phase made basic by DEA addition: separation factor ranges between 2.08 and 1.15 and resolution factor between 7.0 and 1.0. Using the same CSP and 2-propanol doped with TFA as acidic modifier, 10 compounds were enantioseparated with separation factor ranging between 1.40 and 1.04 and resolution factor between 3.1 and 0.3. The use of ethanol as alcoholic modifier also has the advantage of better solubility of the compounds in the mobile phase. The nature of the substituent (electron donating or withdrawing) affects in general the separation factor. A memory effect that involves a long equilibration time of the CSP is present when switching from an acidic mobile phase to a basic one. Chirality, 2008. © 2009 Wiley-Liss, Inc. [source] Enantiomeric separation of imidazolinone herbicides using chiral high-performance liquid chromatographyCHIRALITY, Issue 3 2007Kunde Lin Abstract Chiral high-performance liquid chromatography (HPLC) is one of the most powerful tools to prepare enantiopure standards of chiral compounds. In this study, the enantiomeric separation of imidazolinone herbicides, i.e., imazethapyr, imazapyr, and imazaquin, was investigated using chiral HPLC. The enantioselectivity of Chiralpak AS, Chiralpak AD, Chiralcel OD, and Chiralcel OJ columns for the three analytes was compared under similar chromatographic conditions. Chiralcel OJ column showed the best chiral resolving capacity among the test columns. The resolved enantiomers were distinguished by their signs of circular dichroism detected at 275 nm and their structures confirmed with LC-mass spectrometric analysis. Factors affecting the chiral separation of imidazolinones on Chiralcel OJ column were characterized. Ethanol acted as a better polar modifier than the other alcohols including 2-propanol, 1-butanol, and 1-pentanol. Although the acidic modifier in the mobile phase did not influence chiral recognition, it was necessary for reducing the retention time of enantiomers and suppressing their peak tailing. Thermodynamic evaluation suggests that enantiomeric separation of imidazolinones on Chiralcel OJ column is an enthalpy-driven process from 10 to 40°C. This study also shows that small amounts of pure enantiomers of imidazolinones may be obtained by using the analytical chiral HPLC approach. Chirality 19, 2007. © 2006 Wiley-Liss, Inc. [source] Chiral HPLC separation and CD spectra of the enantiomers of the alkaloid tacamonine and related compoundsCHIRALITY, Issue 10 2001Salvatore Caccamese Abstract The HPLC enantiomeric separation of racemic indole alkaloids tacamonine, 17,-hydroxytacamonine, deethyleburnamonine, and vindeburnol was accomplished using Chiralpak AD and Chiralcel OD as chiral stationary phases. Small structural differences affect the enantioselectivity ability of these phases. Single enantiomers of tacamonine and vindeburnol were isolated by semipreparative HPLC and their CD spectra and optical rotations were measured. Chirality 13:691,693, 2001. © 2001 Wiley-Liss, Inc. [source] Enantiomers of 2-[(Acylamino)ethyl]-1,4-benzodiazepines, Potent ligands of ,-opioid receptor: Chiral chromatographic resolution, configurational assignment, and biological activityCHIRALITY, Issue 9 2001O. Azzolina Abstract Compounds 2a and 3a,e are racemic 2-[(acylamino)ethyl]-1,4-benzodiazepines, tifluadom analogs, with high affinity and selectivity towards the ,-opioid receptor. We describe the enantiomeric separation of all compounds through liquid chromatography with chiral stationary phases, as well as the resolution of the enantiomers of the most interesting compounds, 2a and 3a, by the semipreparative column Chiralpak AD. The configuration of the resolved enantiomers was investigated: the comparative study of CD and 1H NMR spectra shows that compounds (,)- 2a and (,)- 3a have the same absolute configuration of (+)-(S)-tifluadom. A study on the stereoselective interaction with opiate receptors is reported. Chirality 13:606,612, 2001. © 2001 Wiley-Liss, Inc. 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