Stereochemical revision of xylogranatin F by GIAO and DU8+ NMR calculations

Chirality. 2020 May;32(5):515-523. doi: 10.1002/chir.23189. Epub 2020 Mar 3.

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.

Keywords: DU8+; GIAO NMR calculation; limonoid; natural product; structural reassignment.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Density Functional Theory*
  • Limonins / chemistry*
  • Magnetic Resonance Spectroscopy*
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Limonins