Comparable rates for cleavage of amide and ester bonds through nucleophilic attack by carboxylate anion and general acid catalysis by metal-bound water in a carboxypeptidase a model

Article abstract of DOI:10.1021/ja00039a027

The kinetics of the Cu(II)- or Ni(II)-catalyzed deacylation of the methtyl ester (3) and the N,N-dimethyl amide (4) of 2-carboxy-6-[[2-(4-carboxymethyl)imidazolyl]azo]benzoate was measured in dimethyl sulfoxide containing 5% (v/v) water. Efficient catalys