Toward the antibody-catalyzed chemiluminescence. Design and synthesis of hapten

Article abstract of DOI:10.1016/S0960-894X(98)00080-8

Hapten 4 was synthesized to generate catalytic antibodies triggering chemiluminescence by catalyzing the decomposition of the 1,2-dioxetane 3. The hapten 4 was so designed as to elicit a negatively charged functional group in the antibody combining site to catalyze the β-elimination of the protecting group in 3 as well as to lock the protecting group into an energetically favorable anti-periplanar conformation.