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Data from: Resveratrol’s Hidden Hand: A Route to the Optical Detection of Biomolecular Binding

RMIT University, Australia
Ewan Blanch (Aggregated by)
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ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Adc&rfr_id=info%3Asid%2FANDS&rft_id=https://figshare.com/articles/Resveratrol_s_Hidden_Hand_A_Route_to_the_Optical_Detection_of_Biomolecular_Binding/5956411&rft.title=Data from: Resveratrol’s Hidden Hand: A Route to the Optical Detection of Biomolecular Binding&rft.identifier=5bf54f6d6c99c60b22209db2559d5d17&rft.publisher=RMIT University, Australia&rft.description=Attached file provides supplementary data for linked article. 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.&rft.creator=Ewan Blanch&rft.date=2018&rft.relation=https://dx.doi.org/10.1021/acs.jpcb.7b10278&rft_rights=This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.&rft_rights=CC BY-NC: Attribution-Noncommercial 3.0 AU http://creativecommons.org/licenses/by-nc/3.0/au&rft_subject=Stress response&rft_subject=Resveratrol conformer&rft_subject=Stilbenoid phytoalexin&rft_subject=Biomolecular Binding Resveratrol&rft_subject=Optical Detection&rft_subject=Helical atropisomeric forms&rft_subject=Activity spectra&rft_subject=Tyrosyl-tRNA synthetase&rft_subject=Nonplanar structure &rft_subject=Diastereomeric form&rft_subject=Biochemistry and Cell Biology not elsewhere classified&rft_subject=BIOLOGICAL SCIENCES&rft_subject=BIOCHEMISTRY AND CELL BIOLOGY&rft.type=dataset&rft.language=English Access the data
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CC BY-NC: Attribution-Noncommercial 3.0 AU
http://creativecommons.org/licenses/by-nc/3.0/au

This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License, which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes.

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Attached file provides supplementary data for linked article. 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.

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Activity spectra | Biochemistry and Cell Biology | Biological Sciences | Biochemistry and Cell Biology Not Elsewhere Classified | Biomolecular Binding Resveratrol | Diastereomeric form | Helical atropisomeric forms | Nonplanar structure | Optical Detection | Resveratrol conformer | Stilbenoid phytoalexin | Stress response | Tyrosyl-tRNA synthetase |

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  • Local : 5bf54f6d6c99c60b22209db2559d5d17