NMR solution structure study of one saturated sulphur-containing amides from Glycosmis lucida

Nat Prod Res. 2017 Apr;31(7):791-796. doi: 10.1080/14786419.2016.1244196. Epub 2016 Oct 14.

Abstract

One sulphur-containing amide (N-[2-(4-Hydroxyphenyl)-ethyl]-3-methanesulfonyl-N-methyl-propionamide) which was isolated from Glycosmis lucida Wall ex Huang had a different NMR profile with this kind of compounds' normal case. Based on the information obtained by nuclear magnetic resonance pectroscopy (NMR) and mass spectrometry (MS), its configurations in solution were investigated. The results indicated that the compound would have two stable configurations in solution as the double bond switched between C-N and C-O in an appropriate rate. This phenomenon was clearly exposed by the one dimension selective NOE (1D-NOE) experiments. This conclusion would play an active role in the structure analysis work of this kind of compounds.

Keywords: NMR; NOE; solution structure; sulphur-containing amides.

MeSH terms

  • Amides / chemistry
  • Magnetic Resonance Spectroscopy / methods
  • Mass Spectrometry
  • Molecular Structure
  • Rutaceae / chemistry*
  • Sulfonamides / chemistry
  • Sulfur / chemistry

Substances

  • Amides
  • N-(2-(4-Hydroxyphenyl)-ethyl)-3-methanesulfonyl-N-methyl-propionamide
  • Sulfonamides
  • Sulfur