H-Ras peptide and protein substrates bind protein farnesyltransferase as an ionized thiolate

Biochemistry. 1998 Nov 3;37(44):15555-62. doi: 10.1021/bi981525v.

Abstract

The zinc metalloenzyme protein farnesyltransferase (FTase) catalyzes the alkylation of a cysteine residue of protein substrates with a 15 carbon farnesyl group. We have developed fluorescence assays to directly measure the affinity of the enzyme for peptide and protein (Ras) substrates. A peptide corresponding to the carboxyl terminus of H-Ras binds to FTase in the microM range (KD = 4 microM) at physiological pH; however, the peptide affinity is enhanced approximately 70-fold in a ternary complex with an enzyme-bound farnesyl diphosphate (FPP) analogue, indicating that the two substrates bind synergistically. The pH dependence of substrate binding was also investigated, and two ionizations were observed: for the ternary complex, the pKa values are 8.1, reflecting ionization of the thiol of the free peptide, and 6.4. The pH dependence of the ligand-metal charge-transfer band in the optical absorption spectra of a Co2+-substituted FTase ternary complex suggests that a metal-coordinated thiol ionizes with a pKa of 6.3. These data indicate that metal coordination of the peptide sulfur with the zinc ion in FTase lowers the pKa of the thiol resulting in formation of a bound thiolate at physiological pH.

Publication types

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

MeSH terms

  • Alkyl and Aryl Transferases / chemistry
  • Alkyl and Aryl Transferases / metabolism*
  • Animals
  • Binding, Competitive
  • Cobalt / metabolism
  • Cysteine / metabolism
  • Dansyl Compounds / metabolism
  • Hydrogen-Ion Concentration
  • Oligopeptides / chemistry
  • Oligopeptides / metabolism*
  • Protein Binding
  • Protein Prenylation
  • Proto-Oncogene Proteins p21(ras) / chemistry
  • Proto-Oncogene Proteins p21(ras) / metabolism*
  • Rats
  • Spectrometry, Fluorescence
  • Substrate Specificity
  • Sulfhydryl Compounds / chemistry
  • Sulfhydryl Compounds / metabolism*
  • Zinc / metabolism

Substances

  • Dansyl Compounds
  • Oligopeptides
  • Sulfhydryl Compounds
  • Cobalt
  • Alkyl and Aryl Transferases
  • p21(ras) farnesyl-protein transferase
  • Proto-Oncogene Proteins p21(ras)
  • Zinc
  • Cysteine