Stereochemical Study of the Super Large Tetrakis Alkaloid Alasmontamine A by Means of an Advanced Computational NMR

Int J Mol Sci. 2023 Mar 14;24(6):5572. doi: 10.3390/ijms24065572.

Abstract

1H and 13C NMR chemical shifts of the tetrakis monoterpene indole alkaloid alasmontamine A, with a molecular formula of C84H91N8O12, have been calculated within the DFT framework. Six minimum energy conformers of this alkaloid were identified, and three key configurations that contribute to its NMR shielding constants were established. Several ambiguities in the reported assignment of the NMR chemical shifts of alasmontamine A have been resolved.

Keywords: DFT; DP4+; alasmontamine A; computational 1H and 13C NMR; natural products.

MeSH terms

  • Antineoplastic Agents*
  • Magnetic Resonance Imaging
  • Magnetic Resonance Spectroscopy
  • Secologanin Tryptamine Alkaloids*

Substances

  • alasmontamine A
  • Secologanin Tryptamine Alkaloids
  • Antineoplastic Agents