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Circular dichroism of diglycosyl dichalcogenides in solution and solid state
Tibor Kurtán1, Gennaro Pescitelli, Piero Salvadori
1Department of Organic Chemistry, University of Debrecen, H-4010 Debrecen, Hungary. kurtant@tigris.klte.hu
Chirality
|August 10, 2007
Summary
Chiral carbohydrate moieties influence the helicity of diglycosyl disulfides. This study confirms a quadrant rule for disulfide and diselenide chirality, applicable in solution and solid states.
Area of Science:
- Carbohydrate Chemistry
- Spectroscopy
- Chiroptical Methods
Background:
- Diglycosyl disulfides possess inherent chirality due to the disulfide bond.
- Carbohydrate moieties can perturb the electronic properties and conformation of the disulfide chromophore.
- Understanding the relationship between molecular structure and chiroptical properties is crucial for molecular recognition and materials science.
Purpose of the Study:
- To investigate the relationship between low-energy circular dichroism (CD) transitions and the helicity of diglycosyl disulfides.
- To explore the influence of chiral carbohydrate substituents on the disulfide chromophore's helicity.
- To validate the applicability of a quadrant rule for predicting chirality in disulfide and diselenide systems.
Main Methods:
- Solution and solid-state Circular Dichroism (CD) spectroscopy.
- X-ray crystallography for structural determination.
- Time-Dependent Density Functional Theory (TDDFT) CD calculations.
Main Results:
- All investigated diglycosyl disulfides exhibited M helicity in both solution and solid states, with specific dihedral angles.
- Solid-state CD spectra correlated well with X-ray structures.
- TDDFT calculations confirmed the relevance of a quadrant rule for diselenide systems, analogous to disulfides.
Conclusions:
- The study establishes a clear correlation between CD spectral data and the helicity of diglycosyl disulfides.
- The findings support the general applicability of the quadrant rule for predicting the chirality of disulfide and diselenide compounds.
- This research provides insights into the chiroptical behavior of sulfur- and selenium-containing biomolecules.
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