Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 19, Pages 6411-6414Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201900911
Keywords
chiral selectors; cyclodextrins; enzymes; liquid chromatography; supramolecular chemistry
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Funding
- European Social Fund [100234741]
- German Research Foundation (DFG) [FOR RO 2652/1-1]
- Free State of Saxony (SMWK)
- European Union (EFRE) [100185265]
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Large-ring cyclodextrins (CD) are cyclic glucans composed of 9 or more -1,4-linked glucose units. They are minor side products of bacterial glucanotransferases (CGTases, EC2.4.1.19) 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.
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