114(P52) 生物・化学発光性イミダゾピラジノンの合成(ポスター発表の部)

概要

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Imidazopyrazinones with conjugated substitutents at 6,8-position were prepared from the corresponding 3,5-disubtitued-2-aminopyrazines which were synthesized from commercially available 2-aminopyrazine by a sequence of reactions including Pd mediated Stille coupling as a key step. The synthesized imidazopyrazinones showed chemiluminescence in DMSO in the presence of a catalyst. Conjugation at 6-position resulted in obvious bathochromic shift of luminescence. Imidazopyrazinone with phenylethenyl substituent at 8-postion showed orange colored luminescence under slightly acidic conditions whereas yellow luminescence occurred under basic conditions. Imidazopyrazinones are widely utilized by bioluminescent organisms in marine environment. The synthetic method described herein could be applied for naturally occurring bioluminescent imidazopyrazinones as well as their analogues. For examples, coelenterazine precursor and Cypridina luciferin analogue were synthesized. Benzofuran analogue of Cypridina luciferin reacted with luciferase to give luminescence but the light yield was about 1/25, which may due to low ability of chemiluminescence.
天然有機化合物討論会の論文
1996-09-02