24 セレンテラジン系生物発光の遷移状態モデルの合成(口頭発表の部)

抄録

Coelenterazine is well known as a chromogenic compound of aequorin and as luciferin of various bioluminescent marine organisms including the sea pansy Renilla reniformis and the deepsea shrimp Oplophorus gracilorostris. The luminescent reaction was basically accepted as an oxidation reaction in which several key peroxy intermediates and/or transition-states seem to be involved. We have developed a new method to synthesize imidazopyrazinones by using Pd-mediated cross couplings. To investigate the process of bioluminescence reaction and the chiral environment of its transiton-state, we designed a number of new stable coelenterazine analogs and transition-state analogs with an indanone core structure. These analogs were synthesized in 11 steps. Having examined the inhibitory activities for bioluminescence reaction, we found proteinous components in bioluminescence showed different specificity for the chiral transition-state analogs. It suggests that the transition-state analogs might be useful to investigate the chiral environment of bioluminescent reactions.