Synthesis and evaluation of 3-acyltetronic acid-containing metal complexing agents

Potential metal chelators containing one or several acyltetronic acid moieties were prepared from cyclic or acyclic amines and polyamines, and from bis(phenols) by reaction with 1-4 equiv of 3-bromoacetyltetronic acid in the presence of potassium carbonate. The affinity constants of the chelating agents for toxic metallic cations Cd2+, Cs+, and Pb2+ and for dimethylarsinic acid were measured, at pH 7.5 and 9.3. Compound 4, an acyclic triamine containing four acyltetronic moieties, was found to complex efficiently all the tested species.