Ethyl bromoacetimidate, a NH2-specific heterobifunctional reagent. Model reactions with ribonuclease.

doi:10.1515/BCHM2.1979.360.2.1257

Paper

Ethyl bromoacetimidate, a NH2-specific heterobifunctional reagent. Model reactions with ribonuclease.

Published 1979 · J. Diopoh, M. Olomucki

Hoppe-Seyler's Zeitschrift fur physiologische Chemie

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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.

Study Snapshot

Ethyl bromoacetimidate is a short-distance crosslinker that can be used to explore the microenvironment of essential lysine residues in enzyme active sites.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Ethyl bromoacetimidate, a NH2-specific heterobifunctional reagent. Model reactions with ribonuclease.

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