13th International Symposium on & Chemiluminescence Symposium Abstract

Synthesis and bioluminescent activities of the luciferin analogs

Masaki M,1 Mamino M,1 Nakamura M,1 Matsui R,1 Kojima S,2 Ohmiya Y,2 Maki S,1 Hirano T,1 Niwa H1 1. Department of Applied Physics and Chemistry, The University of Electro-Communications, Chofu, Tokyo 182-8585, Japan 2. The Special Division for Human Life Technology, National Institute of Advanced Industrial Science and Technology (AIST), Ikeda, Osaka 563-8577, Japan

The -like snail Latia neritoides inhabits stony bottomed, clear and shallow streams on the North Island in New Zealand. Of the luminescent , Latia is the only bioluminescent animal lives its whole life cycle in fresh water. On stimulation physically or chemically, the snails secret mucus, from which greenish light (λmax = 536 nm) is emitted. During the predator paying attention to the twinkling green balls that move downstream, the snails are thought to escape from the predator. Shimomura reported that the bioluminescent system of Latia exhibits a typical luciferin-luciferase reaction in the presence of oxygen. Our recent study indicated that the bioluminescence system is required none of cofactors but is able to produce green light only with the luciferin and the purified luciferase component, clearly indicating that the light emitter is present in the luciferase, as suggested by Shimomura. The luciferin has a characteristic enol formate structure and the 2,6,6-trimethyl cyclohexene ring system same as vision pigment, retinal. Previous works suggested that the enol formate moiety is essential functionality for the bioluminescent reaction. However, the chemical structure of light emitter and precise mechanism of the bioluminescent reaction are still unclear. In order to clarify the relation ship between the structure and bioluminescence activity, we synthesized various Latia luciferin analogs modified at enol formate moiety and 2,6,6-trimethyl cyclohexene ring system, and their bioluminescent activities were studied, the results for which will be presented.

This is a preprint of an article accepted for publication in Luminescence: Copyright 2004 John Wiley & Sons, Ltd