2019
DOI: 10.1177/1934578x19849311
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Integrated X-Ray, NMR, ECD, and Computational Approaches to Assign the Stereochemistry of Nortriterpenoids

Abstract: Highly oxygenated nortriterpenoids are the principle bioactive chemical constituents isolated from plants of the genera Schisandra and Kadsura. The stereochemistry of these molecules remains a highly challenging problem to solve. To establish the stereochemistry and develop a general nuclear magnetic resonance-electric circular dichroism-computational approach to solve these complex metabolites, we reviewed the published methods to solve the stereochemistry of these triterpenoids. A key goal of this review is … Show more

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Cited by 2 publications
(1 citation statement)
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“…To determine the absolute configuration of metabolites, singlecrystal X-ray diffraction, NMR advanced Mosher's methods (for alcohols), Marfey's method (for aminoacids) are often used (Bhushan and Brückner, 2011;Cimmino et al, 2017). Computational approaches such as density functional theory (DFT) coupled with (i) NMR, (ii) chiroptical methods e.g., electronical circular dichroism (ECD), vibrational circular dichroism (VCD) spectroscopy and (iii) optical rotation are being successfully employed in identification of relative and absolute configuration of marine natural products (Merten et al, 2015;Batista et al, 2018;Menna et al, 2019;Wang and Hamann, 2019;Fan et al, 2020;Marcarino et al, 2020;Zhu and Sun, 2020). The elucidation of biosynthetic pathways from genomic sequence data is also used to support the absolute configuration assignment (Hu et al, 2018;Kim et al, 2020).…”
Section: Extraction Fractionation Isolation Structure Elucidationmentioning
confidence: 99%
“…To determine the absolute configuration of metabolites, singlecrystal X-ray diffraction, NMR advanced Mosher's methods (for alcohols), Marfey's method (for aminoacids) are often used (Bhushan and Brückner, 2011;Cimmino et al, 2017). Computational approaches such as density functional theory (DFT) coupled with (i) NMR, (ii) chiroptical methods e.g., electronical circular dichroism (ECD), vibrational circular dichroism (VCD) spectroscopy and (iii) optical rotation are being successfully employed in identification of relative and absolute configuration of marine natural products (Merten et al, 2015;Batista et al, 2018;Menna et al, 2019;Wang and Hamann, 2019;Fan et al, 2020;Marcarino et al, 2020;Zhu and Sun, 2020). The elucidation of biosynthetic pathways from genomic sequence data is also used to support the absolute configuration assignment (Hu et al, 2018;Kim et al, 2020).…”
Section: Extraction Fractionation Isolation Structure Elucidationmentioning
confidence: 99%