The catalytic activity of the antibody H11 is shown to reside chiefly
in its ability to hydrolyze 1-acetoxybutadiene to crotonaldehyde and t
o promote the cycloaddition of the intermediate enol with N-alkylmalei
mides. This conclusion is based upon the demonstration that the enol t
automerizes too rapidly in solution to be a competent intermediate and
that under the reaction conditions for H11, no cycloaddition occurs w
ith crotonaldehyde and N-ethylmaleimide. As a first step towards a str
uctural understanding of the chemistry of H11, chemical modification e
xperiments have shown that reactions of acidic amino acids, tyrosine,
lysine, and histidine, but not arginine, inhibit the reactions mediate
d by H11.