Synthesis of the protein cutting reagent iron (S)-1-(p-bromoacetamidobenzyl)ethylenediaminetetraacetate and conjugation to cysteine side chains

Bioconjug Chem. 1997 Jan-Feb;8(1):44-8. doi: 10.1021/bc9600731.

Abstract

Convenient methodology for preparation and conjugation of the protein-cutting iron chelate iron (S)-1-(p-bromoacetamidobenzyl) ethylenediaminetetraacetate (Fe-BABE) is given. This formulation of the reagent can be handled in a manner analogous to many other protein-labeling reagents, such as fluorescent probes or cross-linkers. By taking advantage of the recently discovered peptide hydrolysis reaction, the chelate may be tethered to a single site (e.g., a cysteine side chain) and used to map its proximity to individual peptide bonds by automated Edman sequencing of the protein fragments produced. The method is illustrated by conjugation of Fe-BABE to the carboxy terminal domain (amino acid residues 234-329) of the Escherichia coli RNA polymerase alpha subunit. The molecular mass of the protein conjugate was confirmed by electrospray ionization mass spectrometry.

Publication types

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

MeSH terms

  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Cysteine / chemistry
  • Cysteine / metabolism*
  • Edetic Acid / analogs & derivatives*
  • Edetic Acid / chemical synthesis
  • Edetic Acid / metabolism
  • Iron Chelating Agents / chemical synthesis*
  • Iron*
  • Magnetic Resonance Spectroscopy
  • Organometallic Compounds / chemical synthesis*
  • Organometallic Compounds / metabolism
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Iron Chelating Agents
  • Organometallic Compounds
  • 1-(4-bromoacetamidobenzyl)EDTA
  • Edetic Acid
  • Iron
  • Cysteine