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Published on: February 7, 2017
Cyclodextrin complexes: chiral recognition and complexation behaviour
Zsolt Bikádi1, Róbert Iványi, Lajos Szente
1Virtua Drug, Ltd., H-1015 Budapest, Csalogany St. 4C, Hungary.
Current Drug Discovery Technologies
|November 30, 2007
Summary
Cyclodextrins can separate chiral molecules, but predicting this ability computationally is challenging. Stable complex geometry during molecular dynamics simulations can predict chiral recognition, as shown with beta-methyl-tryptophans and alpha-cyclodextrin.
Area of Science:
- Supramolecular Chemistry
- Computational Chemistry
- Analytical Chemistry
Background:
- Cyclodextrins are host molecules used in supramolecular chemistry for molecular encapsulation.
- Chiral separation of racemates using cyclodextrins is common, but the underlying recognition mechanism remains unclear.
- Accurate in silico prediction of chiral recognition is needed.
Purpose of the Study:
- To investigate the chiral recognition mechanism of cyclodextrins.
- To develop a computational method for predicting chiral separation.
- To compare computational predictions with experimental data.
Main Methods:
- Molecular docking and molecular dynamics simulations were performed.
- Stability constants were determined experimentally.
- Capillary electrophoresis was used for enantioseparation measurements.
- Amino acids and methylderivatized tryptophan were used as model guests with alpha-cyclodextrin as the host.
Main Results:
- A positive correlation was observed between binding strength and chiral separation ability.
- Molecular docking energy differences were within the error range, limiting its predictive power.
- Stable complex geometry during molecular dynamics simulations emerged as a key factor for chiral recognition.
- The hypothesis was validated using beta-methyl-tryptophans, where complex geometry predicted separation.
Conclusions:
- While binding strength correlates with chiral separation, it's insufficient for accurate in silico prediction.
- Stable complex geometry, identified through molecular dynamics, is crucial for cyclodextrin-mediated chiral recognition.
- This study provides a validated computational approach for predicting cyclodextrin-based chiral separations.
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