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Syntheses of the mechanism-based inhibitors of coelenterazine bioluminescence
Hideshi Nakamura*1; C Wu1; M Kato1; M Kimura1; S Inouye2
(1) Div. of Biomodeling, Dept. of Bioagricultural Sci., Nagoya University, Nagoya 464-8601, Japan; (2) Yokohama Research Center, Chisso Co., 5-1 Okawa, Kanazawa-ku, Yokohama 236-8605, Japan. *(firstname.lastname@example.org)
Imidazopyrazinones were well known to be involved in bioluminescent reactions such as jellyfish and sea firefly. They emit light with or without proteinous components, defined as bio- and chemiluminescence, respectively, however, the efficiency largely increases with a proteinous component especially in water media. 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 new method to synthesize imidazopyrazinones by using Pd-mediated cross couplings and examined inhibitory activities of stable coelenterazine and transition-state analogs having an indanone core structure. Proteinous components in bioluminescence showed different specificity for the chiral transition-state analogs suggesting that the transition-state analogs might be useful to investigate the chiral environment of bioluminescent reactions.
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