Ethyl bromoacetimidate, a NH2-specific heterobifunctional reagent. Model reactions with ribonuclease.
Hoppe Seylers Z Physiol Chem, 1979/9;360(9):1257-62.
PMID: 41807
Abstract
Ethyl bromoacetimidate was designed as a potential reagent for cross-linking protein NH2 groups with a vicinal nucleophile. The chemical properties of this compound were studied by model reactions with small molecules. Ethyl bromoacetimidate amidinates lysine residues in ribonuclease at pH 9. In a second step, at lower pH values, one of the bromoacetamidino groups bound to the enzyme alkylates a proximal histidine residue. This substitution is pH-dependent with a sharp optimum at 5.6, the same as was earlier observed for alkylation of histidine-119: histidine-12 by halogenoacetates and halogenoacetamides. A common mechanism is suggested for all these types of alkylation. Ethyl bromoacetimidate thus appears as a short-distance crosslinker which can be used, for example, to explore chemically the microenvironment of an essential lysine residue of an enzyme within the active site.
MeSH terms
Acetamides; Animals; Cattle; Cross-Linking Reagents; Cyanogen Bromide; Hydrogen-Ion Concentration; Imidoesters; Kinetics; Pancreas; Peptide Fragments; Protein Binding; Ribonucleases
More resources
EndNote: Download