Resveratrol's Hidden Hand: A Route to the Optical Detection of Biomolecular Binding

Chatterjee, S, Olsen, S, Blanch, E and Wang, F 2018, 'Resveratrol's Hidden Hand: A Route to the Optical Detection of Biomolecular Binding', Journal of Physical Chemistry B, vol. 122, no. 11, pp. 2841-2850.


Document type: Journal Article
Collection: Journal Articles

Title Resveratrol's Hidden Hand: A Route to the Optical Detection of Biomolecular Binding
Author(s) Chatterjee, S
Olsen, S
Blanch, E
Wang, F
Year 2018
Journal name Journal of Physical Chemistry B
Volume number 122
Issue number 11
Start page 2841
End page 2850
Total pages 10
Publisher American Chemical Society
Abstract 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-1 in the ROA and at 1642 and 3834 cm-1 in the VCD spectra of Z-resveratrol that may be useful for this purpose.
Subject Engineering not elsewhere classified
Physical Sciences not elsewhere classified
Chemical Sciences not elsewhere classified
Keyword(s) Orbital Momentum Distributions
Density-Functional Theory
Circular-Dichroism
Estrogen-Receptor
CIS-Resveratrol
AB-Initio
Life-Span
Basis-Set
Wine
Isomerization
DOI - identifier 10.1021/acs.jpcb.7b10278
Copyright notice © 2018 American Chemical Society
ISSN 1520-6106
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