Synthesis of desthio prenylcysteine analogs: sulfur is important for biological activity

Bioorg Med Chem Lett. 2005 Nov 15;15(22):5080-3. doi: 10.1016/j.bmcl.2005.07.075. Epub 2005 Sep 23.

Abstract

N-Acetyl-S-farnesyl cysteine (AFC) is the minimal synthetic substrate for the enzyme Icmt, which methylates prenylated proteins. The desthio-AFC isostere 2 has been synthesized in racemic form. This analog was not an Icmt substrate, but instead a weak inhibitor with an IC50 of approximately 325 microM.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cysteine / analogs & derivatives*
  • Cysteine / chemical synthesis*
  • Inhibitory Concentration 50
  • Methyltransferases / antagonists & inhibitors
  • Methyltransferases / metabolism
  • Molecular Structure
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Terpenes / chemistry
  • Terpenes / metabolism

Substances

  • Sulfides
  • Terpenes
  • Methyltransferases
  • Cysteine