Aminoalkylphosphonofluoridate derivatives: rapid and potentially selective inactivators of serine peptidases

Phosphonic acid analogs of N-Cbz-alanine and N-Cbz-phenylalanine have been converted to the ester and amide fluoridates and evaluated as inactivators of elastase (EC 3.4.21.11) and chymotrypsin (EC 3.4.21.1). These inhibitors, which mimic the natural peptide substrates, are the most potent inactivators of elastase and chymotrypsin yet reported, showing a modest selectivity which correlates with the substrate specificity of the two enzymes.