Conformational preferences of zampanolide and dactylolide

Org Lett. 2013 Oct 18;15(20):5246-9. doi: 10.1021/ol402462h. Epub 2013 Oct 8.

Abstract

The solution conformation behavior of the macrolide core of microtubule-stabilizing agents (-)-zampanolide and (-)-dactylolide has been determined through a combination of high-field NMR experiments and computational modeling. Taken together, the results demonstrate that in solution both molecules exist as a mixture of three interconverting conformational families, one of which bears strong resemblance to zampanolide's tubulin-bound conformation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Lactones / chemistry*
  • Macrolides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Monte Carlo Method
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • Lactones
  • Macrolides
  • dactylolide
  • zampanolide