Resveratrol’s Hidden Hand: A Route to the Optical Detection of Biomolecular Binding
| Autor: | Feng Wang, Subhojyoti Chatterjee, Seth Olsen, Ewan W. Blanch |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
Circular dichroism
Spectrophotometry Infrared Stereochemistry Stereoisomerism Resveratrol Spectrum Analysis Raman 010402 general chemistry 01 natural sciences chemistry.chemical_compound Tyrosine-tRNA Ligase Stilbenes Materials Chemistry Humans Physical and Theoretical Chemistry Binding site Conformational isomerism Binding Sites Molecular Structure 010405 organic chemistry Chemistry Circular Dichroism Optical Imaging Diastereomer 3. Good health 0104 chemical sciences Surfaces Coatings and Films Vibrational circular dichroism Quantum Theory Raman optical activity |
| Zdroj: | The Journal of Physical Chemistry B. 122:2841-2850 |
| ISSN: | 1520-5207 1520-6106 |
| Popis: | Resveratrol is a stilbenoid phytoalexin with promising myriad health benefits predominantly contributed by the trans ( E) diastereomeric form. A recent study has implicated the cis ( Z) diastereomer in human health. This stereoisomer binds with high affinity to human tyrosyl-tRNA synthetase, initiating a downstream cascade that promotes the expression of genes associated with the cellular stress response. We discovered that the nonplanar structure of the cis-resveratrol conformer possesses certain chiral signals in its simulated vibrational circular dichroism (VCD) and Raman optical activity (ROA) spectra. These features may be used for the optical detection of the binding event and in understanding the more diversified biological roles of trans-resveratrol over cis-resveratrol. We use a density functional theory model, which is validated against the known results for the E diastereomer. The Z diastereomer is significantly nonplanar and can exist in two helical atropisomeric forms. These forms exchange rapidly in solution, but only one is observed to bind with the synthetase. This suggests that the binding may generate an enantiomeric excess, leading to detectable changes in the vibrational optical activity spectra. We identify candidate features at 998, 1649, and 1677 cm |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|