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A γ-cyclodextrin duplex connected with two disulfide bonds: synthesis, structure and inclusion complexes
Sergey Volkov1, Lukáš Kumprecht, Miloš Buděšínský
1Institute of Organic Chemistry and Biochemistry AS CR, v.v.i., Flemingovo nám. 2, 166 10 Prague 6, Czech Republic. kraus@uochb.cas.cz.
Organic & Biomolecular Chemistry
|January 24, 2015
Summary
Researchers synthesized a novel gamma-cyclodextrin duplex with a large tubular cavity. This structure forms highly stable inclusion complexes with steroids and bile acids, demonstrating significant binding affinities.
Area of Science:
- Supramolecular Chemistry
- Organic Synthesis
- Structural Biology
Background:
- Cyclodextrins (CDs) are cyclic oligosaccharides with hydrophobic cavities capable of forming inclusion complexes.
- Gamma-cyclodextrin (γ-CD) possesses a larger cavity compared to alpha- and beta-cyclodextrins, offering potential for complexing larger guest molecules.
- Developing novel CD derivatives with enhanced properties is crucial for advanced host-guest chemistry.
Purpose of the Study:
- To synthesize and characterize a novel γ-cyclodextrin duplex structure.
- To investigate the structural features of the γ-cyclodextrin duplex, particularly its cavity dimensions.
- To evaluate the binding affinities of the γ-cyclodextrin duplex with steroid and bile acid molecules.
Main Methods:
- Selective debenzylation of Per(2,3,6-tri-O-benzyl)-γ-cyclodextrin using DIBAL-H.
- Separation and isolation of isomeric diol products.
- Transformation of the C2-symmetrical diol into a dithiol and subsequent dimerization.
- Crystal structure determination of the γ-cyclodextrin duplex.
- Determination of binding affinities using techniques like isothermal titration calorimetry (ITC) or surface plasmon resonance (SPR) (implied).
Main Results:
- A mixture of isomeric diols was obtained, with the C6(I),C6(V) isomer isolated.
- The C2-symmetrical C6(I),C6(V) diol was successfully dimerized into a γ-cyclodextrin duplex structure.
- Crystal structure analysis revealed a tubular cavity with slight elliptical distortion and a solvent-accessible volume of approximately 740 ų.
- The γ-cyclodextrin duplex exhibited high binding affinities for steroids and bile acids, ranging from 5.3 × 10⁷ M⁻¹ to 1.9 × 10⁸ M⁻¹.
Conclusions:
- A novel γ-cyclodextrin duplex with a well-defined tubular cavity has been synthesized and structurally characterized.
- The large cavity of the γ-cyclodextrin duplex enables the formation of highly stable inclusion complexes with steroidal guest molecules.
- This γ-cyclodextrin duplex represents a promising host molecule for applications involving the recognition and binding of steroids and bile acids.
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