Relevant bibliographies by topics / Enantioseparation

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  1. Journal articles
  2. Dissertations / Theses
  3. Books
  4. Book chapters
  5. Conference papers

Academic literature on the topic 'Enantioseparation'

Author: Grafiati
Published: 4 June 2021
Last updated: 9 March 2023

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Journal articles on the topic "Enantioseparation"

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Zhao, Yuan, Xuecheng Zhu, Wei Jiang, Huilin Liu, and Baoguo Sun. "Chiral Recognition for Chromatography and Membrane-Based Separations: Recent Developments and Future Prospects." Molecules 26, no. 4 (February 21, 2021): 1145. http://dx.doi.org/10.3390/molecules26041145.

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With the rapid development of global industry and increasingly frequent product circulation, the separation and detection of chiral drugs/pesticides are becoming increasingly important. The chiral nature of substances can result in harm to the human body, and the selective endocrine-disrupting effect of drug enantiomers is caused by differential enantiospecific binding to receptors. This review is devoted to the specific recognition and resolution of chiral molecules by chromatography and membrane-based enantioseparation techniques. Chromatographic enantiomer separations with chiral stationary phase (CSP)-based columns and membrane-based enantiomer filtration are detailed. In addition, the unique properties of these chiral resolution methods have been summarized for practical applications in the chemistry, environment, biology, medicine, and food industries. We further discussed the recognition mechanism in analytical enantioseparations and analyzed recent developments and future prospects of chromatographic and membrane-based enantioseparations.
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Čižmáriková, R., A. Némethy, J. Valentová, K. Hroboňová, and K. Bruchatá. "Synthesis and HPLC Enantioseparation of Derivatives of the 3-hydroxyphenylethanone." Acta Facultatis Pharmaceuticae Universitatis Comenianae 59, no. 2 (December 28, 2012): 15–27. http://dx.doi.org/10.2478/v10219-012-0023-7.

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AbstractWithin the framework of the study of the synthesis and high-performance liquid chromatography (HPLC) enantioseparation the series of 9 derivatives of 3-hydroxyphenylethanone was prepared by a well-tried method. The structure of the prepared compounds was confirmed on the basis of interpretation of the IR, UV, 1H NMR and 13C NMR spectra. An enantioseparation of prepared compounds was performed using HPLC on a native teicoplanin (Chirobiotic T) and the amylose tris (3,5-dimethylphenylcarbamate) (Chiralpak AD) chiral stationary phases, which is more suitable for the enantioseparation of all prepared compounds especially with heterocycles in the basic part of a molecule.
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Zhang, Qiongwen, Junyuan Zhang, Xia Wang, Jia Yu, and Xingjie Guo. "Enantioseparation of Eight Pairs of Tetralone Derivative Enantiomers on Cellulose Based Chiral Stationary Phase by HPLC." Current Pharmaceutical Analysis 16, no. 5 (June 15, 2020): 539–47. http://dx.doi.org/10.2174/1573412915666181130111103.

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Background: Tetralone derivatives, important resources for the development of new drugs which can act in the treatment of central nervous system disorders or participate in synthesis reaction for the synthesis of various pharmaceuticals, have great research value and a bright prospect in exploitation. Methods: A novel chiral HPLC method for efficient enantioseparation of eight tetralone derivative enantiomers was developed on cellulose based CHIRALPAK IC chiral stationary phase under normal mode by investigating the effects of type and content of organic modifier, column temperature and flow rate on retention and enantioselectivity. Besides, the specificity, linearity, stability, precision, accuracy and robustness of this method were also validated. Results: Satisfactory enantioseparation was obtained for all enantiomers in n-hexane/2-propanol mobile phase system at ambient temperature. The thermodynamic study indicated that the solute transfer from the mobile to stationary phase was enthalpically favorable, and the process of enantioseparation was mainly enthalpy controlled. This method met the requirements for quantitative determination of tetralone derivative enantiomers. Conclusion: This study can provide great and important application value for enantioseparation of eight pairs of newly synthesized tetralone derivative enantiomers under normal mode using CHIRALPAK IC chiral column.
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Čižmáriková, R., S. Chudáčiková, J. Valentová, and A. Némethy. "Synthesis and enantioseparation of derivatives of propranolol." Acta Facultatis Pharmaceuticae Universitatis Comenianae 59, no. 1 (January 1, 2012): 5–13. http://dx.doi.org/10.2478/v10219-012-0012-x.

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Synthesis and enantioseparation of derivatives of propranololPropranolol is one of the first prepared and in therapeutic praxis used beta- adrenolytics. In this paper novel derivatives of propranolol with cyclohexylamino and pyrrolidin-1-yl groups in hydrophilic part were prepared. HPLC-enantioseparation propranolol (as reference compound) and of the prepared derivatives has been achieved using a Chiralpak AD CSP based on the amylose tris (3,5-dimethylphenylcarbamate).(R)-enantiomer of the propranolol was prepared by stereoselective synthesis using Jacobsen catalyst.
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Chen, Ming, Xinling Lu, Xiaofei Ma, Yin Xiao, and Yong Wang. "Click preparation of multiple-thioether bridged cyclodextrin chiral materials for efficient enantioseparation in high-performance liquid chromatography." Analyst 146, no. 9 (2021): 3025–33. http://dx.doi.org/10.1039/d1an00145k.

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YASHIMA, EIJI, and YOSHIO OKAMOTO. "Chiral Membranes for Enantioseparation." Sen'i Gakkaishi 51, no. 4 (1995): P150—P155. http://dx.doi.org/10.2115/fiber.51.4_p150.

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Eichhorn, Ralf. "Enantioseparation in microfluidic channels." Chemical Physics 375, no. 2-3 (October 2010): 568–77. http://dx.doi.org/10.1016/j.chemphys.2010.06.021.

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Gössi, Angelo, Wolfgang Riedl, and Boelo Schuur. "Enantioseparation with liquid membranes." Journal of Chemical Technology & Biotechnology 93, no. 3 (October 19, 2017): 629–44. http://dx.doi.org/10.1002/jctb.5417.

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Lao, Wenjian. "Thermodynamic and Extrathermodynamic Studies of Enantioseparation of Imidazolinone Herbicides on Chiralcel OJ Column." ISRN Chromatography 2013 (May 16, 2013): 1–9. http://dx.doi.org/10.1155/2013/460787.

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A homologous series of chiral imidazolinone herbicide was previously resolved on Chiralcel OJ column in high performance liquid chromatography. However, the mechanism of the chiral separation remains unclear. In this study, chromatographic behaviors of five chiral imidazolinone herbicides were characterized by thermodynamic and extrathermodynamic methods in order to enhance the understanding of the chiral separation. Thermodynamic parameters of this study were derived from equilibrium constant () that was estimated from the moment analysis of the chromatographic peak. Van't Hoff plots of ( versus ) were linear at a range of 15–50°C, only nonlinear at a range of 5–15 °C with n-hexane (0.1%, trifluoroacetic acid)-2-propanol 60/40 (v/v) mobile phase. The enantiomer retention on the chiral column was entropy-driven at a lower temperature (5°C) and enthalpy-driven at a higher temperature (10 to 50°C). Enantioseparations of four of the five imidazolinone herbicides were enthalpy-driven, only entropy-driven for imazaquin. Enantioseparation mechanisms were different in between 5–10°C and 15–50°C probably due to the conformational change of the OJ phase. Enthalpy-entropy compensation showed similar mechanisms in retention and chiral separation for the five or enantiomers. Several extrathermodynamic relationships were able to be extracted to address additivity of group contribution.
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Peluso, Paola, Alessandro Dessì, Roberto Dallocchio, Barbara Sechi, Carlo Gatti, Bezhan Chankvetadze, Victor Mamane, et al. "Enantioseparation of 5,5′-Dibromo-2,2′-dichloro-3-selanyl-4,4′-bipyridines on Polysaccharide-Based Chiral Stationary Phases: Exploring Chalcogen Bonds in Liquid-Phase Chromatography." Molecules 26, no. 1 (January 4, 2021): 221. http://dx.doi.org/10.3390/molecules26010221.

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The chalcogen bond (ChB) is a noncovalent interaction based on electrophilic features of regions of electron charge density depletion (σ-holes) located on bound atoms of group VI. The σ-holes of sulfur and heavy chalcogen atoms (Se, Te) (donors) can interact through their positive electrostatic potential (V) with nucleophilic partners such as lone pairs, π-clouds, and anions (acceptors). In the last few years, promising applications of ChBs in catalysis, crystal engineering, molecular biology, and supramolecular chemistry have been reported. Recently, we explored the high-performance liquid chromatography (HPLC) enantioseparation of fluorinated 3-arylthio-4,4′-bipyridines containing sulfur atoms as ChB donors. Following this study, herein we describe the comparative enantioseparation of three 5,5′-dibromo-2,2′-dichloro-3-selanyl-4,4′-bipyridines on polysaccharide-based chiral stationary phases (CSPs) aiming to understand function and potentialities of selenium σ-holes in the enantiodiscrimination process. The impact of the chalcogen substituent on enantioseparation was explored by using sulfur and non-chalcogen derivatives as reference substances for comparison. Our investigation also focused on the function of the perfluorinated aromatic ring as a π-hole donor recognition site. Thermodynamic quantities associated with the enantioseparation were derived from van’t Hoff plots and local electron charge density of specific molecular regions of the interacting partners were inspected in terms of calculated V. On this basis, by correlating theoretical data and experimental results, the participation of ChBs and π-hole bonds in the enantiodiscrimination process was reasonably confirmed.
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Dissertations / Theses on the topic "Enantioseparation"

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Grudzien, Lukasz Andrzej. "Enantioseparation using a counter-current bioreactor." Thesis, Brunel University, 2011. http://bura.brunel.ac.uk/handle/2438/6496.

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The potential of countercurrent chromatography (CCC) as a small footprint bioreactor/separator for manufacture of enantiopure chiral molecules was explored, using as a model reaction the isolation of L-amino butyric acid (L-ABA) from a DL-ABA racemate and the enantioselectivity of D-amino acid oxidase (DAAO). Bioconversion of D-ABA to ketobutyric acid (KBA) by DAAO, immobilised by selective partitioning in the stationary phase of the CCC centrifuge, was accompanied by separation of unreacted L-ABA from KBA by the countercurrent action of the centrifuge. For effective bioreactor/separator action, a high partition of the biocatalyst to the stationary phase was required in order to retain the biocatalyst in the coil, with differing partitions of substrates and products between the stationary phase (SP) and mobile phase (MP) so that these could be separated. Aqueous two-phase systems (ATPS) were the major two-phase systems used to provide SP and MP, as these are well reported to be effective in preserving enzyme activity. The distribution ratios of DL-ABA, KBA and DAAO were measured in a range of phases with polyethylene glycols (PEGs) of different molecular weights, different salts, and different compositions of PEG and salt, using an automated robotic method, developed for the purpose. A system of 14% w/w PEG 1000/ 14% w/w potassium phosphate, pH 7.6, gave the best combination of distributions ratios (CPEG phase/Csalt phase = CSP/CMP) for ABA, KBA and biocatalyst (DAAO) of 0.6, 2.4 and 19.6 respectively. A limited number of aqueous-organic and ionic liquid two-phase systems were also reviewed, but found unsatisfactory. CCC operating conditions such as substrate concentration, biocatalyst concentration, the mobile phase flow rate (residence time in the CCC coil), temperature, rotational speed and operational modes (single flow and multiple-dual flow) and types of mixing (cascade and wave-like) were optimised to produce total conversion of D-ABA to KBA, which was then completely separated from unreacted, enantiomerically pure (>99% ee), LABA. Advantages of the CCC bioreactor over conventional technology include reduced equipment footprint, cheaper running costs, and faster purifications. However, in its current format the drawbacks, such as enzyme instability and excessive optimisation time, reduce its commercial appeal. Additional investigations into the use of whole cell preparations of biocatalyst in the CCC bioreactor showed potential to overcome the problem of enzyme instability and this may in the future give the CCC bioreactor a place in the enantioseparation field.
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Snyder, Chad. "Enantioseparation of Alkylaryl Sulfoxides Using Capillary Zone Electrophoresis." TopSCHOLAR®, 1999. https://digitalcommons.wku.edu/theses/3040.

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Alkylaryl sulfoxides possess a chiral sulfur atom easily identifiable by capillary zone electrophoresis (CZE). Separation of chiral alkylaryl sulfoxides has already been accomplished by modified method of CZE known as micellar electrokinetic chromatography (MEKC). However, no articles have been published on the enantioseparation of alkylaryl sulfoxides using capillary zone electrophoresis. A series of sulfoxides were synthesized, purified and identified via NMR. Enantioseparation was performed using CZE employing a 10 mmol. Phosphate buffer (pH 4.0, 25% acetonitrile, 2% sulfated-β-cyclodextrin). Synthesis of these sulfoxides will be presented along with the results of the procedure’s optimization. Separation of the sulfoxide enanitomers relies on the partitioning between the chiral additive (sulfated-β-cyclodextrin) and buffer solution.
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Chen, Taiyi. "Chloroperoxidase Catalyzed Enantioselective Epoxidation of Selected Olefins and Regiospecific Degradation of Dimethylsulfoniopropionate." FIU Digital Commons, 2011. http://digitalcommons.fiu.edu/etd/514.

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Chloroperoxidase (CPO), secreted by marine fungus Caldariomyces fumago, is the most versatile catalyst among known heme enzymes. Chloroperoxidase can catalyze epoxidation reactions with high enantioselectivity and high yield, which makes CPO an attractive candidate for both industrial and medicinal chiral synthesis. Toward this end, we have constructed two CPO mutants, F103A and N74V. Chiral HPLC was used to evaluate the enantioselectivity and yield of CPO and the mutants toward the epoxidation of styrene and its derivatives. Both of the mutants show dramatically changed epoxidation profiles compared to the parent protein. This information provided fresh insight into the mechanism through which CPO achieves its enantioselectivity. Furthermore, effort was made to understand the biological function of CPO through characterization of CPO catalyzed oxidation of dimethylsulfoniopropionate (DMSP), a secondary metabolite of many marine algal species that plays a pivotal role in marine ecology and global climate.
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Wahl, Joachim [Verfasser], and Ulrike [Gutachter] Holzgrabe. "The Use of Ionic Liquids in Capillary Electrophoresis Enantioseparation / Joachim Wahl ; Gutachter: Ulrike Holzgrabe." Würzburg : Universität Würzburg, 2019. http://d-nb.info/117907968X/34.

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Didier, Delphine. "Functionalized analogues of Tröger's base: synthesis, enantioseparation, and application as a chiral scaffold in organocatalysis." Doctoral thesis, Universite Libre de Bruxelles, 2009. http://hdl.handle.net/2013/ULB-DIPOT:oai:dipot.ulb.ac.be:2013/210277.

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Jusqu’à très récemment, les catalyseurs pour la synthèse asymétrique étaient limités aux enzymes et aux complexes de coordination. Depuis les années 2000, une troisième approche a vu le jour: l’organocatalyse asymétrique. Il est assez surprenant de constater que parmi la multitude de catalyseurs organiques développés chaque année, une minorité d’entre eux seulement est basée sur de nouveaux squelettes chiraux. En effet, l’introduction d’une nouvelle entité chirale pourrait mener à la découverte de nouvelles combinaisons de substrats ainsi qu’à de nouvelles réactions catalytiques hautement stéréosélectives. C’est pourquoi, nous nous sommes proposé de préparer une série de nouveaux catalyseurs organiques bifonctionnels incluant des fonctions thiourées et basée sur le squelette chiral de la base de Tröger.

L’accès aux dérivés énantiopures de la base de Tröger reste un défi majeur. C’est pourquoi, nous avons décidé de mettre au point une méthode efficace et prévisible, pour la résolution des analogues de la base de Tröger. Dans la mesure où l’élaboration d’une telle méthode nécessite un grand nombre de molécules, nous avons synthétisé une série de dérivés de la base de Tröger.

La condensation d’anilines variablement substituées avec du paraformaldehyde dans de l’acide trifluoroacétique a été étudiée, conduisant à la synthèse d’analogues symétriques de la base de Tröger. L’utilisation de paraformaldehyde n’étant pas compatible avec tous les groupements fonctionnels, d’autres voies de synthèse ont également été explorées. Ainsi, des dérivés amino et cyano ont été préparés par l’intermédiaire de réactions organométalliques. Ensuite, une voie de synthèse menant aux analogues non-symétriques de la base de Tröger a été mise au point. Finalement, une série de dérivés présentant un pont –NCH2CH2N- a été préparée.

La résolution de l’ensemble des composés a été systématiquement étudiée par chromatographie sur la phase stationnaire chirale commerciale Whelk O1. Des relations structure vs. énantioséléctivité ont pu être établies permettant de prédire la séparation par notre méthode. Une corrélation entre l’ordre d’élution et la configuration absolue a également pu être mise en évidence.

Enfin, l’activité catalytique des dérivés thiourées de la base de Tröger a été évaluée dans la réaction d’addition de Michael de différents dérivés de l’acide malonique au trans-nitrostyrene. Compte tenu de la faible basicité de la base de Tröger, il a été démontré que l’issue de la réaction est fortement dépendante du pKa du nucléophile. De plus, aucune stéréosélectivité n’a pu être mise en évidence dans cette réaction d’addition.


Doctorat en Sciences
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Levkin, Pavel. "Practice and theory of gas chromatographic enantioseparation on single- and binary-selector chiral stationary phases." [S.l. : s.n.], 2007.

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Bortoleto, Marcela Armelim. "Avaliação de fungos na obtenção do metabólito quiral e ativo O-desmetilvenlafaxina." Universidade de São Paulo, 2014. http://www.teses.usp.br/teses/disponiveis/59/59138/tde-08082014-122129/.

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A venlafaxina é um fármaco quiral utilizado no tratamento da depressão e da ansiedade associada à depressão. A ação farmacológica desse fármaco está associada principalmente ao enantiômero (+)-(S)-venlafaxina, que inibe a recaptação da serotonina enantiosseletivamente. Quando metabolizada pelas enzimas da citocromo P450 dois metabólitos são produzidos, também quirais, a O-desmetilvenlafaxina (ODV) e a N-desmetilvenlafaxina (NDV). O estudos mostram que o metabólito ODV é farmacologicamente ativo, apresentando ação farmacológica semelhante a venlafaxina. Fungos são micro-organismos capazes de mimetizar o metabolismo de mamíferos, produzindo, muitas vezes, os mesmos metabólitos. Além disso, esse processo pode ser enantiosseletivo. Dessa forma, o objetivo desse trabalho foi avaliar a capacidade de fungos em biotransformar a venlafaxina em seus metabólitos ODV e NDV de uma maneira enantiosseletiva. A separação quiral dos analitos foi realizada por cromatografia liquida de alta eficiência (CLAE) e eletroforese capilar (CE). Como técnica de preparação de amostra foi empregada a microextração liquido-liquido dispersiva (DLLME). Essa técnica recente de preparação de amostra possui alta eficiência na extração, permitindo a obtenção de altos valores de recuperação e um consumo mínimo de solvente orgânico. Anterior aos estudos de biotransformação, o método foi validado para análise por CLAE e CE, empregando, em ambos os casos, a DLLME como técnica de preparação de amostras. A validação foi realizada de acordo com as recomendações da ANVISA para análise de fármacos em material biológico. Todos os parâmetros avaliados (linearidade, precisão, exatidão, estabilidade, seletividade e limite de quantificação) apresentaram valores dentro das exigências da ANVISA. Os estudos de biotransformação foram realizados empregando os seguintes fungos: Mucor rouxii, Cunninghamella echinulata ATCC 8688A, Cunninghamella elegans 10028B, Beuveria bassiana ATCC 7159, Phomopsis sp (TD2), Chaetomiun globosun (VR10) e Glomerela cingulata (VA1). Entre esses, o fungo Cunninghamella elegans mostrou-se promissor na biotransformação da venlafaxina. Dessa forma, diversos fatores foram avaliados na tentativa de melhorar a biotransformação, sendo esses: troca de fonte de carbono do meio de cultura, alteração de meios de biotransformação e adição de cofatores ao meio de cultura. Os resultados mostraram fortes indícios de biotransformação enantiosseletiva da venlafaxina em seu metabólito (+)-(S)-N-desmetilvenlafaxina.
Venlafaxine is a chiral drug used in the treatment of depression and anxiety associated with depression. The pharmacological activity of this drug is mainly associated to the enantiomer (+)-(S)-venlafaxine, which inhibits the reuptake of serotonin with enantioselectivity. When metabolized by the cytochrome P450 enzymes, two metabolites, also chiral, are produced, O-desmethylvenlafaxine (ODV) and N-desmethylvenlafaxine (NDV). The studies have demonstrated that the ODV metabolite is pharmacologically active, with similar pharmacological activity of venlafaxine. Fungal are microorganisms capable of mimicking the mammalian metabolism, often producing the same metabolites. Moreover, this process can be enantioselective. Thus, the aim of this study was to evaluate the ability of fungi to biotransform, with enantioselectivity, the venlafaxine in its metabolites ODV and NDV. The chiral separation of the analytes was performed by high performance liquid chromatography (HPLC) and capillary electrophoresis (CE). As sample preparation was employed the dispersive liquid-liquid microextraction (DLLME). This recent technique of sample preparation has high extraction efficiency, allowing obtaining high values of recovery and minimal consumption of organic solvent. Before the biotransformation studies, the method was validated employing CE and HPLC with the DLLME technique as sample preparation. The validation was performed according to ANVISA recommendations. All parameters (linearity, precision, accuracy, stability, selectivity and limit of quantification) were acceptable as required by ANVISA. The biotransformation studies were conducted using the following fungal: Mucor rouxii, Cunninghamella echinulata ATCC 8688A, Cunninghamella elegans 10028B, Beuveria bassiana ATCC 7159, Phomopsis sp (TD2), Chaetomiun globosun (VR10) and Glomerela cingulata (VA1). Among these, the fungus Cunninghamella elegans was promising in the biotransformation of venlafaxine. Thus, several factors were evaluated in an attempt to improve the biotransformation: carbon source exchange in the liquid culture medium, changes of the biotransformation medium and addition of cofators in the culture medium. The results provides strong evidences of enantioselective biotransformation of venlafaxine in its metabolite (+)-(S)-N-desmethylvenlafaxine.
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Fortes, Simone Silveira. "Avaliação de fungos na biotransformação estereosseletiva da Hidroxizina e obtenção do metabólito quiral e ativo Cetirizina." Universidade de São Paulo, 2013. http://www.teses.usp.br/teses/disponiveis/59/59138/tde-11072013-103307/.

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Modelos microbiológicos tem sido usado na biotransformação de fármacos para a obtenção de metabólitos. Fungos de diversos gêneros têm sido amplamente utilizados para mimetizar o metabolismo hepático de mamíferos. O uso de fungos é vantajoso uma vez que apresentam um crescimento rápido e de fácil formação do sistema multienzimático. Além disso, hoje, a biotransformação é considerada como uma tecnologia econômica e competitiva, na busca de novas rotas de produção farmacêutica e de compostos agrotóxicos. Em muitos casos a transformação biológica é enantiosseletiva, permitindo a produção de enantiômeros puros a partir de misturas racêmicas. Devido à ausência de um método de extração com baixo consumo de solventes orgânicos para a determinação enantiosseletiva da hidroxizina (HZ) e cetirizina (CTZ), foi desenvolvido um método que combina a microextração liquido-liquido dispersiva (DLLME) e eletroforese capilar (CE) para estudar a biotransformação enantiosseletiva da HZ pelos fungos Penicillium crustosum, Mucor rouxii, Cunnonghamella echinulata var. elegans ATCC 8688, Cunnonghamella echinulata var. elegans ATCC 10028, Nigrospora sphaerica e Fusarium oxysporum. Um método por CE foi desenvolvido para a análise enanatiosseletiva da hidroxizina e cetirizina em meio de cultura Czapek. As análises por CE foram realizadas utilizando um capilar de sílica fundida não revestida, 50 mmol L-1 de borato de sódio como solução tampão de análise (pH 9,0) contendo 0,8% p/v de ciclodextrina--sulfatada como seletor quiral. A tensão aplicada e temperatura foram de +6 kV e 15 ºC, respectivamente. O detector UV foi ajustado no comprimento de onda 214 nm. As condições da DLLME envolvidas foram: clorofórmio (300 µL) como solvente extrator, etanol (400 µL) como solvente dispersante. Após a formação da solução turva, as amostras foram submetidas a agitação por vórtex durante 30 segundos a 2000 rpm e centrifugação durante 5 minutos a 3000 rpm. As recuperações foram na faixa de 87,4 91,7%. O método se mostrou linear na faixa de concentração 250 12500 ng mL-1 para cada enantiômero da HZ (r > 0.998) e de 125 6250 ng mL-1 para cada enantiômero da CTZ (r > 0.998). Os limites de quantificação foram 125 e 250 ng mL-1 para CTZ e HZ, respectivamente. Dentre os seis fungos estudados, três foram capazes de converter a HZ em CTZ enantiosseletivamente, especialmente o fungo Cunninghamella elegans ATCC 10028 que converteu 19% de (E1)-HZ em (S)-CTZ com excesso enantiomérico de 65%.
Microbial models have been used in biotransformation studies of many drugs aiming their metabolite production. Fungi of various genera have been extensively used to mimic the mammals hepatic metabolism. The use of fungi is advantageous because they present fast growth and easy formation of the multienzymatic system. Moreover, the biotransformation is, nowadays, considered an economically and competitive technology, in the search of new production routes for fine chemical, pharmaceutical and agrochemical compounds. In many cases, the biological transformation is enantioselective, allowing the production of pure enantiomers from racemic mixtures. In light of the above considerations and due to the absence of a low consuming organic solvent extraction method for the enantioselective determination of hydroxyzine (HZ) and cetirizine (CTZ), it was developed a method combining dispersive liquid-liquid microextraction (DLLME) and capillary electrophoresis (CE) to study the enantioselective biotransformation of HZ through the fungi Penicillium crustosum, Mucor rouxii, Cunnonghamella echinulata var. elegans ATCC 8688, Cunnonghamella echinulata var. elegans ATCC 10028, Nigrospora sphaerica e Fusarium oxysporum. A CE method was developed for the enantioselective analysis of hydroxyzine (HZ) and cetirizine (CTZ) in Czapek liquid culture medium. The CE analyses were performed using an uncoated fused-silica capillary and 50 mmol/L sodium borate buffer (pH 9.0) containing 0.8% (w/v) sulfated--cyclodextrin. The applied voltage and temperature used were +6 kV and 15 °C, respectively. The UV detector was set at 214 nm. The DLLME conditions involved: chloroform (300 µL) as extraction solvent and ethanol (400 µL) as dispersive solvent. After the formation of the cloudy solution, the samples were subjected to vortex agitation during 30 s at 2000 rpm and centrifugation for 5 min at 3000 rpm. The recoveries were in the range of 87.4 91.7%. The method was linear over the concentration range of 250 12500 ng/mL for each enantiomer of HZ (r > 0.998) and of 125 6250 ng/mL for each enantiomer of CTZ (r > 0.998). The quantification limits were 125 and 250 ng/mL for CTZ and HZ, respectively. Among the six studied fungi three were able to convert HZ to CTZ enantioselectively, especially the fungus Cunninghamella elegans ATCC 10028B that converted 19% of (E1)-HZ to (S)-CTZ with an enantiomeric excess of 65%.
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Zanão, Lídia Renata. "Avaliação de fungos e complexos de salen na obtenção do metabólito quiral e ativo terbutalina." Universidade de São Paulo, 2013. http://www.teses.usp.br/teses/disponiveis/59/59138/tde-26112013-203126/.

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Enantiômeros podem interagir de maneira diferenciada no organismo, ocasionando efeitos farmacológicos variados. Dessa forma, metodologias para a obtenção de fármacos enantiomericamente puros são importantes para a indústria farmacêutica. Modelos sintéticos empregando reagentes quirais, como complexos de salen e modelos biológicos utilizando fungos estão sendo muito estudados neste contexto. O uso de fungos apresenta como principais vantagens o crescimento rápido, baixo custo e fácil operação, além da produção de metabólitos em grande quantidade. Complexos de salen são eficientes e estáveis, possuindo ampla aplicabilidade e possibilidade de produzir reações enantiosseletivas. O objetivo deste trabalho foi avaliar fungos e complexo de salen como alternativas na produção enantiosseletiva de terbutalina, o metabólito quiral e ativo de seu pró-fármaco, o bmbuterol. A separação enantiosseletiva dos analitos foi realizada empregando a cromatografia líquida de alta eficiência com detector UV-Vis (LC/UV). A validação da metodologia analítica e os estudos de biotransformação foram executados por cromatografia líquida de alta eficiência acoplada à espectrometria de massas (LC-MS). A resolução do bambuterol e da terbutalina por LC/UV foi realizada utilizando como fase estacionária a coluna Chirobiotic T e como fase móvel acetonitrila:metanol (80:20, v/v) + 0,3% de ácido fórmico e 0,1% de trietilamina, numa vazão de 1,5 mL min-1 e por LC-MS utilizando a mesma fase estacionária e a fase móvel composta por 96% de metanol em água + 0,2% de ácido acético e 0,1% de acetato de amônio na vazão de 1 mL min-1. A extração dos analitos em meio de cultura líquido (Czapek, 2 mL) foi feita empregando a microextração liquido-liquido dispersiva (DLLME), nas condições: solvente dispersor,isopropanol (600 µL); solvente extrator, diclorometano (50 µL); reagente par iônico, di(2-etil-hexil)fosfato (100µL); e solução tampão fosfato de sódio (2 mL, pH 7,6). A recuperação do bambuterol foi de 92% e a da terbutalina foi estimada em 55%. O método foi validado para a análise do bambuterol no meio de cultura e se mostrou linear na faixa de concentração 500 17500 ng mL-1 para cada enantiômero (r > 0.998).O limite de quantificação foi igual a 500 ng mL-1. Dentre os fungos avaliados neste trabalho, nenhum foi capaz de realizar a biotransformação do bambuterol em terbutalina nas condições empregadas. Nos estudos feitos utilizando catálise assimétrica também não foi possível observar esse metabólito. Dada a complexidade do metabolismo do bambuterol (reações de hidrólise e/ou oxidação) e da formação de vários intermediários anterior a etapa de formação da terbutalina, as condições avaliadas nesse estudo não foi capaz de produzir o metabólito ativo do bambuterol, terbutalina.
Enantiomers may interact differently in the organism causing pharmacological sundry effects. For these reason, enantiomeric pure drugs are very important for the pharmaceutical industries. Synthetic models employing chiral reagents, like salen complexes, and biological models using fungi are been very studied in this context. Fungi present as main advantage the fast growing up, low costs and easily application, moreover, their metabolites are produced in huge quantities. Salen complexes are efficient and stable. They have a wide application and the possibility of production of high enantiomeric excess. The aim of this work was to evaluate fungi and salen complex as alternatives to the enantioselective production of terbutaline, the chiral and active metabolite of your prodrug, bambuterol. The analytes enantioselective separation was done employing high performance liquid chromatography with UV-Vis detector (LC/UV). The method validation and the studies of biotransformation were done using high performance liquid chromatography coupled with mass spectrometry (LC-MS). The resolution of bambuterol and terbutaline by LC/UV was accomplished using the Chirobiotic T column and acetonitrile: methanol (80:20, v/v) + 0.3% formic acid and 0.1% triethylamine as mobile phase at a flow rate of 1.5 mL min-1 and by LC-MS employing the same column and the mobile phase was composed by 96% of methanol in water + 0,2% acetic acid and 0,1% ammonium acetate at a flow rate of 0.1 mL min-1. The analytes extraction of the culture medium (Czapek, 2 mL) was done using the dispersive liquid liquid microextraction (DLLME), in the following conditions: dispersive solvent, isopropanol (600 µL); extractor solvent, dichloromethane (50 µL); ionic-pair reagent; di(2-ethylhexyl)phosphate (100 µL); and sodium phosphate buffer (2 mL, pH 7.6). The recoveries were 92% for the bambuterol and estimated in 55% for terbutaline. The method was validated for the analysis of bambuterol in the culture medium and was linear over the concentration range of 500 17500 ng mL-1 for each enantiomer (r > 0.998). The quantification limit was 500 ng mL-1. Among the evaluated fungi, none was able to do the biotransformation process of bambuterol at terbutaline in the employed conditions and so do the studies employing asymmetric catalyses. Because the complexity of bambuterols metabolism for producing terbutaline (hydrolysis and/or oxidation reactions) and the formation of several intermediates before the terbulalines formation step, the evaluated conditions in this study were not able to produce the chiral active metabolite, terbutaline.
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10

Wang, Bin. "Utility of Cationic and Anionic Chiral Surfactants in Capillary Electrophoresis (CE) and CE Coupled to Mass Spectrometry (CE-MS)." Digital Archive @ GSU, 2009. http://digitalarchive.gsu.edu/chemistry_theses/16.

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The research presented in this thesis involves the application of chiral cationic and anionic surfactants for simultaneous enantioseparation of structurally similar compounds in capillary electrophoresis (CE) and CE coupled to mass spectrometry (CE-MS). The first chapter briefly introduces the fundamentals of CE and CE-MS, emphasizing the micellar electrokinetic chromatography (MEKC) and MEKC-MS techniques, as well as ionic liquids (ILs) and affinity CE (ACE). In chapter 2, a mixture of five racemic profen (PROF) drugs are simultaneously separated with the combined use of 2,3,6-tri-O-methyl-β-cyclodextrin (TM-β-CD) and IL-type surfactant, N-undecenoxycarbonyl-L-leucinol bromide (L-UCLB). Enantioseparations of these PROFs are optimized using a standard recipe containing 35.00 mM TM-β-CD, 5.00 mM sodium acetate at pH 5.0, and varying the concentration as well as chain length of the IL surfactants. The batch-to-batch reproducibility of L-UCLB is found to be acceptable in terms of enantiomeric resolution, and migration time. A competitive inhibition mechanism is proposed to investigate the ternary interactions among TM-β-CD, ILs, and PROFs. The apparent binding constant of TM-β-CD to L-UCLB is estimated by nonlinear and linear plotting methods. The binding constants of one representative PROF (e.g., fenoprofen) to TM-β-CD and to L-UCLB are estimated by a secondary plotting approach. The R- and S-fenoprofen having different binding constant values, resulting in the enantioseparation due to the synergistic effect of TM-β-CD and L-UCLB. The R- and S-configurations of barbiturates display differences in potency and biological activity. In Chapter 3, a multivariate MEKC-ESI-MS approach for the simultaneous analysis of the racemic mixture of three barbiturates is presented. The chiral selector employed is the polymeric surfactant polysodium N-undecenoxycarbonyl-L-isoleucinate. The central composite design is used to optimize the chiral resolution, decrease the total analysis time, and improve the ESI-MS signal-to-noise ratio for these barbiturates. In preliminary experiments, the ranges of the factors investigated in the multivariate approaches are determined. Then the multivariate optimizations are conducted to determine the best overall chiral resolution with shortest possible run times for barbiturates. The limit of detection of ESI-MS is several folds higher compared to the UV detection. The predicted optimum results are in good agreement with the experimental data.
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Books on the topic "Enantioseparation"

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Chromatographic enantioseparation: Methods and applications. 2nd ed. New York: E. Horwood, 1991.

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Allenmark, Stig G. Chromatographic enantioseparation: Methods and applications. Chichester, West Sussex, England: E. Horwood, 1988.

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Bryant, C. H. Data mining for chemistry: The application of three machine induction tools to a database of enantioseparations. Manchester: UMIST, 1996.

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Chromatographic Enantioseparation: Methods and Applications. Ellis Horwood Ltd, 1988.

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Allenmark, Stig G. Chromatographic Enantioseparation: Methods and Applications. John Wiley & Sons Australia Ltd, 1988.

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Book chapters on the topic "Enantioseparation"

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Brückner, Hans, Mathias Langer, Ali Esna-Ashari, Anik Labudda, Zbigniew J. Kamiński, Miroslaw T. Leplawy, and Rolf Jöster. "Enantioseparation of Cα-disubstituted glycines." In Amino Acids, 159–65. Dordrecht: Springer Netherlands, 1990. http://dx.doi.org/10.1007/978-94-011-2262-7_19.

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Dubey, Rituraj, and Ravi Bhushan. "Enantioseparation by Thin-Layer Chromatography." In Methods in Molecular Biology, 35–44. New York, NY: Springer New York, 2019. http://dx.doi.org/10.1007/978-1-4939-9438-0_2.

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Borst, Claudia, and Ulrike Holzgrabe. "Cyclodextrin-Mediated Enantioseparation in Microemulsion Electrokinetic Chromatography." In Methods in Molecular Biology, 363–75. Totowa, NJ: Humana Press, 2012. http://dx.doi.org/10.1007/978-1-62703-263-6_23.

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Chen, Yi, and Lijuan Song. "Enantioseparation by Chiral Ligand-Exchange Capillary Electrophoresis." In Methods in Molecular Biology, 393–407. Totowa, NJ: Humana Press, 2012. http://dx.doi.org/10.1007/978-1-62703-263-6_25.

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Li, Xiaoxuan, and Yong Wang. "HPLC Enantioseparation on Cyclodextrin-Based Chiral Stationary Phases." In Methods in Molecular Biology, 159–69. New York, NY: Springer New York, 2019. http://dx.doi.org/10.1007/978-1-4939-9438-0_9.

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Wang, Yong, and Siu Choon Ng. "HPLC Enantioseparation on Cyclodextrin-Based Chiral Stationary Phases." In Methods in Molecular Biology, 69–79. Totowa, NJ: Humana Press, 2012. http://dx.doi.org/10.1007/978-1-62703-263-6_4.

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Chankvetadze, Bezhan. "Monolithic Chiral Stationary Phases for Liquid-Phase Enantioseparation Techniques." In Monolithic Silicas in Separation Science, 231–48. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527633241.ch12.

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Malik, Poonam, and Ravi Bhushan. "Analysis and Enantioseparation of Amino Acids by Liquid Chromatography." In Methods in Molecular Biology, 219–36. New York, NY: Springer New York, 2019. http://dx.doi.org/10.1007/978-1-4939-9639-1_17.

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Chankvetadze, Bezhan. "Chiral Recognition and Enantioseparation Mechanisms in Capillary Electrokinetic Chromatography." In Chiral Recognition in Separation Methods, 97–152. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/978-3-642-12445-7_5.

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Schurig, Volker, and Diana Kreidler. "Gas-Chromatographic Enantioseparation of Unfunctionalized Chiral Hydrocarbons: An Overview." In Methods in Molecular Biology, 45–67. Totowa, NJ: Humana Press, 2012. http://dx.doi.org/10.1007/978-1-62703-263-6_3.

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Conference papers on the topic "Enantioseparation"

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YU, H. W., and C. B. CHING. "PREPARATIVE ENANTIOSEPARATION OF FLUOXETINE BY SIMULATED MOVING BED." In Proceedings of the Third Pacific Basin Conference. WORLD SCIENTIFIC, 2003. http://dx.doi.org/10.1142/9789812704320_0027.

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Huang, Dushu, Wei Liu, Zhaolong Huang, Yashun Chen, Jing Wang, and Na Wu. "Enantioseparation of Enantiomers across Hollow Fiber Supported Liquid Membranes." In 2012 International Conference on Biomedical Engineering and Biotechnology (iCBEB). IEEE, 2012. http://dx.doi.org/10.1109/icbeb.2012.195.

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Huang, Dushu, Wei Liu, Lihua Yao, Yong Min, Ruimin Xiao, and Yashun Chen. "Enantioseparation of Propranolol Enantiomers Using Hollow Fiber Membrane Contactor." In 2012 International Conference on Biomedical Engineering and Biotechnology (iCBEB). IEEE, 2012. http://dx.doi.org/10.1109/icbeb.2012.197.

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Shen, Gang-yi, Donglai She, Wanting Yu, and Shuwen Li. "Enantioseparation of Peptides with Two Chiral Centers by Capillary Electrophoresis." In 2012 International Conference on Biomedical Engineering and Biotechnology (iCBEB). IEEE, 2012. http://dx.doi.org/10.1109/icbeb.2012.196.

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Hermawan, Dadan, Ainaya Halwa Lathufa, Cacu, Ponco Iswanto, Uyi Sulaeman, and Hassan Y. Aboul-Enein. "Molecular docking approach for prediction of enantioseparation of miconazole using cyclodextrin derivatives as chiral selector." In VIII INTERNATIONAL ANNUAL CONFERENCE “INDUSTRIAL TECHNOLOGIES AND ENGINEERING” (ICITE 2021). AIP Publishing, 2022. http://dx.doi.org/10.1063/5.0107144.

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HONGWEI, YU, C. B. CHING, FU PING, and S. C. NG. "LIQUID CHROMATOGRAPHIC RETENTION BEHAVIOR AND ENANTIOSEPARATION OF FLUOXETINE ON A NEW β-CYCLODEXTRIN BONDED-PHASE COLUMN." In Proceedings of the Second Pacific Basin Conference. WORLD SCIENTIFIC, 2000. http://dx.doi.org/10.1142/9789812793331_0029.

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Putri, Ulfa Rahmawati, Dwi Siswanta, Dadan Hermawan, and Mudasir Mudasir. "Molecular Docking Approach for Prediction of Enantioseparation of Chiral Ibuprofen by α-1-Acid Glycoprotein Column." In Life Science, Materials and Applied Chemistry. Switzerland: Trans Tech Publications Ltd, 2022. http://dx.doi.org/10.4028/p-ox63hg.

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A study of the molecular anchoring and inclusion complex of the R/S-ibuprofen chiral compound with α-1-acid glycoprotein (AGP) has been carried out. This study aimed to predict the chiral separation of ibuprofen using chiral column filled with AGP protein. The geometrical optimization of R/S-ibuprofen was conducted on different calculation methods to obtain the optimal molecular structure. Molecular docking approaches, specifically docking using AutodockTools software were used to predict R/S-ibuprofen separation in AGP chiral column by comparing the binding energy values and the type of interaction. Results of the study show that the best method for optimizing the geometry of ibuprofen is Density Functional Theory (DFT). Furthermore, the results of the specific anchoring of ibuprofen on the AGP shows that the binding energy of S-ibuprofen with AGP is more negative than that of R-ibuprofen, namely -5.63 and -5.55 kcal/mol, respectively, indicating that S-ibuprofen interacts more strongly with AGP and therefore it will be eluted from the AGP chiral column later after R-ibuprofen.
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Hermawan, Dadan, Cacu Cacu, Nurul Alif Septiorini, Ponco Iswanto, Uyi Sulaeman, and Hassan Y. Aboul-Enein. "Prediction of Enantioseparation of Econazole on the Cyclodextrin Derivatives as Chiral Selectors by Molecular Docking Approach." In Soedirman International Conference on Mathematics and Applied Sciences (SICOMAS 2021). Paris, France: Atlantis Press, 2022. http://dx.doi.org/10.2991/apr.k.220503.002.

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