Synthesis of dehydroalanine fragments as thiostrepton side chain mimetics

Bioorg Med Chem Lett. 2005 May 16;15(10):2457-60. doi: 10.1016/j.bmcl.2005.03.084.

Abstract

Syntheses of dehydroalanine derivatives via a solid-support route, starting from selenocystein, and via conventional solution phase chemistry are described along with initial biological testing. The target compounds were designed as mimetics of the dehydroalanine side chain of the macrocyclic antibiotic thiostrepton that acts on the bacterial ribosome.

Publication types

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

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Chromatography, Liquid
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Mimicry*
  • Thiostrepton / chemistry*
  • Thiostrepton / pharmacology

Substances

  • dehydroalanine
  • Thiostrepton
  • Alanine