Enhanced Chiral Recognition by Cyclodextrin Dimers
Author Information
Author(s): Jens Voskuhl, Kira Schaepe, Bart Jan Ravoo
Primary Institution: Organic Chemistry Institute, Westfälische Wilhelms-Universität Münster
Hypothesis
Multivalent complexes involving multiple host-guest interactions will result in an increased overall binding affinity and enantioselectivity.
Conclusion
Chiral recognition can be enhanced by multivalent interaction, even if not all CD cavities are available for complexation.
Supporting Evidence
- The study synthesized water-soluble chiral guest dimers based on borneol, menthol, and isopinocampheol.
- Isothermal titration calorimetry was used to measure the formation of divalent inclusion complexes.
- Chiral recognition was shown to be amplified even with a substantial fraction of the cavities of the CD dimer not available for complexation.
Takeaway
The study shows that using special molecules can help recognize different shapes better, like how we can tell apart left and right shoes.
Methodology
The interaction of chiral divalent guest molecules with β-cyclodextrin dimers was measured using isothermal titration calorimetry.
Limitations
The dimer largely isomerizes into a pseudorotaxane that preferentially binds in a monovalent rather than a divalent fashion.
Digital Object Identifier (DOI)
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