Impact of dispersion correction in DFT-enhanced anisotropic NMR for stereochemical elucidation of flexible marine natural products.
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| Autori principali: | , , , , , , , , |
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| Natura: | Artículo científico |
| Lingua: | en |
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Marine life science & technology
2025
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| _version_ | 1868266119877361664 |
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| author | Chi, Lu-Ping Li, Xiao-Lu Ketzel, Anton F Navarro-Vázquez, Armando Schattenberg, Caspar J Li, Xiao-Ming Li, Xin Sun, Han Wang, Bin-Gui |
| author_facet | Chi, Lu-Ping Li, Xiao-Lu Ketzel, Anton F Navarro-Vázquez, Armando Schattenberg, Caspar J Li, Xiao-Ming Li, Xin Sun, Han Wang, Bin-Gui Chi, Lu-Ping Li, Xiao-Lu Ketzel, Anton F Navarro-Vázquez, Armando Schattenberg, Caspar J Li, Xiao-Ming Li, Xin Sun, Han Wang, Bin-Gui |
| collection | PubMed - marine biology |
| contents | Impact of dispersion correction in DFT-enhanced anisotropic NMR for stereochemical elucidation of flexible marine natural products. Chi, Lu-Ping Li, Xiao-Lu Ketzel, Anton F Navarro-Vázquez, Armando Schattenberg, Caspar J Li, Xiao-Ming Li, Xin Sun, Han Wang, Bin-Gui Although anisotropic NMR spectroscopy has emerged as a powerful method for determining the relative configuration of complex natural products, major challenges persist with structurally flexible molecules. In this study, we conducted a systematic comparative analysis of stereochemical elucidation, combining anisotropic NMR spectroscopy and density functional theory (DFT) calculations on spiroepicoccin B () and epicoccin V (), which were characterized as thiodiketopiperazine marine natural products isolated from the deep-sea-derived fungus SD-388. For the flexible compound , we compared various conformational sampling approaches, including an assessment of the quality of relative energies within the obtained ensembles. We demonstrated the critical role of dispersion correction within DFT computations to precisely account for weak non-bonded intramolecular interactions. By integrating anisotropic NMR analysis, chemical shifts, electronic circular dichroism, and DFT computations, we determined the absolute configurations and conformational ensembles for and , respectively, highlighting the significance of the intramolecular methyl-π interaction in stabilizing one of the conformers. Our study introduces new strategies to address conformational flexibility in the stereochemical elucidation of challenging organic molecules. The online version contains supplementary material available at 10.1007/s42995-025-00294-w. |
| format | Artículo científico |
| id | pubmed_41322257 |
| institution | PubMed |
| language | en |
| publishDate | 2025 |
| publisher | Marine life science & technology |
| record_format | pubmed |
| spellingShingle | Impact of dispersion correction in DFT-enhanced anisotropic NMR for stereochemical elucidation of flexible marine natural products. Chi, Lu-Ping Li, Xiao-Lu Ketzel, Anton F Navarro-Vázquez, Armando Schattenberg, Caspar J Li, Xiao-Ming Li, Xin Sun, Han Wang, Bin-Gui Impact of dispersion correction in DFT-enhanced anisotropic NMR for stereochemical elucidation of flexible marine natural products. Chi, Lu-Ping Li, Xiao-Lu Ketzel, Anton F Navarro-Vázquez, Armando Schattenberg, Caspar J Li, Xiao-Ming Li, Xin Sun, Han Wang, Bin-Gui Although anisotropic NMR spectroscopy has emerged as a powerful method for determining the relative configuration of complex natural products, major challenges persist with structurally flexible molecules. In this study, we conducted a systematic comparative analysis of stereochemical elucidation, combining anisotropic NMR spectroscopy and density functional theory (DFT) calculations on spiroepicoccin B () and epicoccin V (), which were characterized as thiodiketopiperazine marine natural products isolated from the deep-sea-derived fungus SD-388. For the flexible compound , we compared various conformational sampling approaches, including an assessment of the quality of relative energies within the obtained ensembles. We demonstrated the critical role of dispersion correction within DFT computations to precisely account for weak non-bonded intramolecular interactions. By integrating anisotropic NMR analysis, chemical shifts, electronic circular dichroism, and DFT computations, we determined the absolute configurations and conformational ensembles for and , respectively, highlighting the significance of the intramolecular methyl-π interaction in stabilizing one of the conformers. Our study introduces new strategies to address conformational flexibility in the stereochemical elucidation of challenging organic molecules. The online version contains supplementary material available at 10.1007/s42995-025-00294-w. |
| title | Impact of dispersion correction in DFT-enhanced anisotropic NMR for stereochemical elucidation of flexible marine natural products. |
| url | https://pubmed.ncbi.nlm.nih.gov/41322257/ |