Quantitation of prenylcysteines by a selective cleavage reaction

Proc Natl Acad Sci U S A. 1991 Nov 1;88(21):9668-70. doi: 10.1073/pnas.88.21.9668.

Abstract

The allylic thioether bond of the prenylcysteines of prenylated proteins has been shown to be cleaved by 2-naphthol under alkaline conditions to yield substituted naphthopyrans. These products are readily resolved from interfering materials by HPLC and have a strongly absorbing chromophore. Thus, this reaction is suitable for quantitative analysis of prenyl substituents of proteins, and we have examined a number of tissues for their content of prenylcysteines. These amino acids are present in mammalian tissues at a concentration of 0.36-1.4 nmol/mg of protein, with a ratio of geranylgeranylcysteine to farnesylcysteine in the range of 4 to 10. Prenylcysteines were also found in the cytosolic fraction of two mouse tissues at about one-third the concentration of the whole organ. The level of these modified amino acids was found to be significantly less in a yeast, a fungus, a brown alga, a higher plant, and an insect. Again, geranylgeranylcysteine is predominant. Prenylcysteines were absent from Escherichia coli but present in an archaebacterium. The prenylcysteine content of mammalian tissue is about 1% of that of cholesterol and about equal to that of ubiquinones and dolichols. Calculations indicate that about 0.5% of all proteins are prenylated.

Publication types

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

MeSH terms

  • 3T3 Cells / chemistry
  • Animals
  • CHO Cells / chemistry
  • Chromatography, High Pressure Liquid
  • Cricetinae
  • Cysteine / analogs & derivatives*
  • Cysteine / analysis
  • Cysteine / chemistry
  • Diterpenes / analysis*
  • Diterpenes / chemistry
  • HeLa Cells / chemistry
  • Humans
  • Mevalonic Acid / metabolism
  • Mice
  • Naphthols / chemistry
  • Protein Processing, Post-Translational*

Substances

  • Diterpenes
  • Naphthols
  • geranylgeranylcysteine
  • S-farnesylcysteine
  • Cysteine
  • 2-naphthol
  • Mevalonic Acid