NMR structure determination of brefeldin-A, a 13-membered ring fungal metabolite

Robert Glaser, Dror Shiftan, Mark Froimowitz

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Dissolution of brefeldin-A in CDCl3 afforded two species in the ratio 13: 1. Vicinal proton-proton coupling constants and NOE intensity enhancement measurements showed that the 13-membered ring conformation found by x-ray crystallography in the solid state appears to be preferred also in the solution-state major species. The observance of signals from a solution-state minor species (e.g. for the C-15 methyl) shows that at least one other 13-membered ring conformation exists in a small amount. While some degree of conformational flexibility for the major species cyclopentyl ring cannot be ruled out, the O-13 hydroxyl group is clearly axially disposed in the solution state as it is in the crystal. Comparison of the solution-state 13C NMR chemical shifts of the major species with those values measured by solid-state cross-polarization magic angle spinning show fairly good agreement with differences usually of 1 ppm, or less, with the exception of C-2,8,6,11,15 signals where differences were ca 2-3 ppm.

Original languageEnglish
Pages (from-to)274-280
Number of pages7
JournalMagnetic Resonance in Chemistry
Volume38
Issue number4
DOIs
StatePublished - 1 Jan 2000

Keywords

  • Brefeldin-A
  • C NMR
  • Conformation
  • Cross-polarization magic angle spinning
  • H NMR
  • H-H coupling constants
  • Medium rings
  • NMR
  • Stereochemistry

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