Large-Ring Cyclodextrins as Chiral Selectors for Enantiomeric Pharmaceuticals
| Autor: | Franziska D. Zitzmann, Detlev Belder, Sebastian Thurmann, Yannick Krauke, Christian Sonnendecker, Andrea A. Robitzki, Wolfgang Zimmermann, Cédric Przybylski, Kate Monks, Nicole Heinke |
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| Přispěvatelé: | Leipzig University, Chimie Structurale Organique et Biologique (CSOB), Institut Parisien de Chimie Moléculaire (IPCM), Chimie Moléculaire de Paris Centre (FR 2769), Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Paris - Chimie ParisTech-PSL (ENSCP), Université Paris sciences et lettres (PSL)-Ecole Superieure de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Institut de Chimie du CNRS (INC)-École normale supérieure - Paris (ENS Paris), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Chimie Moléculaire de Paris Centre (FR 2769), Université Paris sciences et lettres (PSL)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Universität Leipzig [Leipzig], Institut für Analytische Chemie |
| Rok vydání: | 2019 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization POLE 3 Cell Survival Complex formation Supramolecular chemistry Bacillus 010402 general chemistry Ring (chemistry) 01 natural sciences Catalysis Cell Line Bacterial Proteins [CHIM]Chemical Sciences Humans Fragmentation (cell biology) Fluvastatin chemistry.chemical_classification Cyclodextrins Chromatography 010405 organic chemistry 010401 analytical chemistry Electrophoresis Capillary Stereoisomerism General Chemistry Reversed-phase chromatography General Medicine 3. Good health 0104 chemical sciences Mefloquine Electrophoresis Enzyme chemistry Pharmaceutical Preparations Glucosyltransferases Enantiomer CSOB |
| Zdroj: | Angewandte Chemie International Edition Angewandte Chemie International Edition, Wiley-VCH Verlag, 2019, ⟨10.1002/ange.201900911⟩ |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/ange.201900911⟩ |
| Popis: | Large-ring cyclodextrins (CD) are cyclic glucans composed of 9 or more α-1,4-linked glucose units. They are minor side products of bacterial glucanotransferases (CGTases, EC 2.4.1.19) and have previously been available only in very small amounts for studies of their properties in supramolecular complex formation reactions. We engineered a CGTase to synthesize mainly large-ring CD facilitating their preparation in larger amounts. By reversed phase chromatography, we obtained single CD samples composed of 10 to 12 glucose units (CD10, CD11, and CD12) with a purity of >90 %. Their identity was confirmed by high resolution mass spectrometry and fragmentation analysis. We demonstrated the non-toxicity of CD10-CD12 for human cell lines by a cell proliferation assay and impedimetric monitoring. We then showed that CD10 and CD11 are efficient chiral selectors for the capillary electrophoretic separation of the enantiomeric pharmaceuticals fluvastatin, mefloquine, carvedilol, and primaquine. |
| Databáze: | OpenAIRE |
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