Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations
Yannan Liu, Tina Holt, Andrei G. Kutateladze, Timothy R. Newhouse
Abstract
Abstract This manuscript describes predicted NMR shifts for the limonoid natural product xylogranatin F. The 1 H and 13 C NMR shifts of four diastereomers were evaluated by GIAO and hybrid DFT/parametric DU8+ methods. The results of the 1 H and 13 C NMR calculations for both the GIAO method and the DU8+ calculations suggest the revised structure that was recently reassigned by chemical synthesis. Furthermore, we show that while DU8+ provides superior accuracy with less computation time, GIAO points to the correct structure with more distinguishable data in this case study.
Topics & Concepts
ChemistryChemical shiftDiastereomerCarbon-13 NMRComputational chemistryStereochemistryPhysical chemistryMolecular spectroscopy and chiralityNatural product bioactivities and synthesisPhytochemistry and Biological Activities