Synthesis of frame-shifted farnesyl diphosphate analogs

Org Lett. 2012 Aug 17;14(16):4038-41. doi: 10.1021/ol300683r. Epub 2012 Aug 2.


A set of synthetic approaches were developed and applied to the synthesis of eight frame-shifted farnesyl diphosphate (FPP) analogs. These analogs bear increased or decreased methylene units between the double bonds and/or diphosphate moieties of the isoprenoid structure. Evaluation versus mammalian FTase revealed that small structural changes can lead to dramatic changes in substrate ability.

Publication types

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

MeSH terms

  • Alkyl and Aryl Transferases / metabolism*
  • Molecular Structure
  • Polyisoprenyl Phosphates / chemical synthesis*
  • Polyisoprenyl Phosphates / chemistry
  • Sesquiterpenes / chemical synthesis*
  • Sesquiterpenes / chemistry
  • Structure-Activity Relationship


  • Polyisoprenyl Phosphates
  • Sesquiterpenes
  • farnesyl pyrophosphate
  • Alkyl and Aryl Transferases
  • p21(ras) farnesyl-protein transferase