Catalytic properties of the antibody H11

The catalytic activity of the antibody H11 is shown to reside chiefly in its ability to hydrolyze 1-acetoxybutadiene to crotonaldehyde and to promote the cycloaddition of the intermediate enol with N-alkylmaleimides. This conclusion is based upon the demonstration that the enol tautomerizes too rapidly in solution to be a competent intermediate and that under the reaction conditions for H11, no cycloaddition occurs with crotonaldehyde and N-ethylmaleimide. As a first step towards a structural understanding of the chemistry of H11, chemical modification experiments have shown that reactions of acidic amino acids, tyrosine, lysine, and histidine, but not arginine, inhibit the reactions mediated by H11.