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A Micropatterning Assay for Measuring Cell Chirality
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Large-Ring Cyclodextrins as Chiral Selectors for Enantiomeric Pharmaceuticals
Christian Sonnendecker1, Sebastian Thürmann2, Cédric Przybylski3
1Dept. of Microbiology and Bioprocess Technology, Institute of Biochemistry, Leipzig University, Johannisallee 23, 04103, Leipzig, Germany.
Angewandte Chemie (International Ed. in English)
|March 19, 2019
Summary
Engineered cyclodextrins (CD) are now available in larger quantities. These large-ring CDs (CD10-CD12) are non-toxic and effective chiral selectors for pharmaceutical enantiomer separation.
Area of Science:
- Carbohydrate Chemistry
- Biotechnology
- Analytical Chemistry
Background:
- Large-ring cyclodextrins (CDs), cyclic glucans with 9+ glucose units, are minor byproducts of bacterial glucanotransferases (CGTases).
- Limited availability of large-ring CDs hindered research into their supramolecular chemistry and applications.
- Previous studies focused on smaller cyclodextrins due to production challenges for larger variants.
Purpose of the Study:
- To engineer a CGTase for enhanced synthesis of large-ring cyclodextrins.
- To prepare and characterize purified large-ring cyclodextrins (CD10, CD11, CD12).
- To evaluate the non-toxicity and chiral separation capabilities of these novel CDs.
Main Methods:
- Enzymatic engineering of CGTase for targeted synthesis of large-ring CDs.
- Reversed-phase chromatography for purification of CD10, CD11, and CD12 samples (>90% purity).
- High-resolution mass spectrometry and fragmentation analysis for structural confirmation.
- Cell proliferation assays and impedimetric monitoring for cytotoxicity assessment.
- Capillary electrophoresis (CE) using CD10 and CD11 as chiral selectors for enantiomeric pharmaceutical separation.
Main Results:
- Successfully engineered a CGTase to produce large-ring CDs in significant amounts.
- Obtained highly pure (>90%) single cyclodextrin samples: CD10, CD11, and CD12.
- Demonstrated the non-toxicity of CD10-CD12 towards human cell lines.
- Confirmed the efficacy of CD10 and CD11 as chiral selectors in CE for separating enantiomers of fluvastatin, mefloquine, carvedilol, and primaquine.
Conclusions:
- Engineered CGTase facilitates the production of large-ring cyclodextrins (CD10-CD12) in preparative quantities.
- These large-ring CDs are non-toxic and suitable for biological applications.
- CD10 and CD11 represent promising chiral selectors for the enantioseparation of key pharmaceutical compounds via capillary electrophoresis.
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