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Syntheses of coelenterazine analogs with a conjugated chromophore at 8-position Chun Wu*1; O Shimomura2; A Murai3; H Nakamura1 (1) Div. of Biomodeling, Dept. of Bioagricultural, Nagoya University, Nagoya city, 464-8601, Japan; (2) Marine Biological Laboratory, Woods Hole, Massachusetts 02543, USA; (3) Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan,      *(i993001d@mbox.media.nagoya-u.ac.jp) 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 deep-sea shrimp Oplophorus gracilorostris. The range of emission maximum of bioluminescence is reported from 450 to 475 nm depending on luciferase species and luminescence conditions. Coelenterazine contains a 6,8-disubstituted imidazopyrazine-3-one ring structure, which was synthesized from 2-aminopyrazine and 2-ketoaldehyde or its equivalents. In the course of our studies, we have established a new synthetic method of 2-amino-3,5-disubstituted pyrazines by using Pd-mediated cross-coupling reactions such as Suzuki coupling, Stille coupling, and Sonogashira reaction. A number of new synthesized analogs of coelenterazine with conjugated olefines or aromatic groups at 8-position showed that a bathochromic effect of luminescence color was caused by the conjugated groups in chemiluminescence. Whereas these analogs gave poor luminescence activity with Renilla luciferase or apoaequorin, with Oplophorus luciferase the bisthienyl analog showed moderate luminescence activity (5% of the total light of coelenterazine) at the longest wave length of 528 nm. [Poster: wu.chun.13532]

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