title: Didehydrofarnesyl diphosphate: an intrinsically fluorescent inhibitor of protein farnesyltransferase.
abstract: Didehydrofarnesyl diphosphate (delta delta FPP), a fluorescent pentaene analogue of farnesyl diphosphate (FPP), was synthesized using stereoselective Wittig reactions. Although delta delta FPP was not an alternative substrate for yeast protein farnesyltransferase (FTase), the fluorescent analogue was a potent competitive inhibitor with a K(i) value of 8.8 microM (K (m) (FPP) = 27 microM).
authors.affiliation: Department of Medicinal Chemistry, The University of Utah, 419 Wakara Way, Suite 205, Salt Lake City, UT 84108-1257, USA.
authors.forename: Xiao-Hui
authors.initials: XH
authors.lastname: Liu
authors.forename: Glenn D
authors.initials: GD
authors.lastname: Prestwich
mesh_terms: D019883:Alkyl and Aryl Transferases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D005456:Fluorescent Dyes / Q000494:pharmacology*; D011106:Polyisoprenyl Phosphates / Q000737:chemistry / Q000494:pharmacology*; D012717:Sesquiterpenes
chemical_list: D004791:Enzyme Inhibitors; D005456:Fluorescent Dyes; D011106:Polyisoprenyl Phosphates; D012717:Sesquiterpenes; C004808:farnesyl pyrophosphate; D019883:Alkyl and Aryl Transferases; C064911:p21(ras) farnesyl-protein transferase