Abstract
中文摘要 利用鈀金屬催化交叉耦合反應合成腔腸螢光素的類似物可用在研究鳶烏賊體內螢光蛋白的發光機制上。薗頭交叉耦合反應可在2-氨基吡嗪的五號位置引入乙炔基。在縮合反應中，使用4-甲基苯磺酸吡啶鹽可讓對酸敏感的乙炔基不受破壞而得到類似物153和160。相較於天然腔腸螢光素149和15，此二類似物的發光波譜可觀察到有助於螢光蛋白發光機制研究的紅位移。而乙炔基的引入使取代基長度增加亦可探討螢光蛋白對類似物的接受度。 腔腸螢光素氧化後的醯胺化合物168a是生物螢光發中機制中的發光器。藉由合成168b-d並量測其發光波譜，可發現類似物的放光相較於天然腔腸螢光素大約有六十至八十奈米的紅位移。 Abstract Many coelenterazine analogs have been synthesized via palladium-mediated cross coupling reactions for bioluminescent studies toward photoprotein Symplectin. Instead of hydrochloric acid, pyridinium p-toluenesulfonate (PPTS) provides a method to obtain coelenterazine analogs containing acid-sensitive moieties. After this method was developed, the analogs having acetylene moieties at 6-position of coelenterazine was synthesized via Sonogashira cross coupling. Analogs 153 and 160 both emit light at longer wavelength compared to natural coelenterazine 149 and 15 which are suitable for protein studies. Besides, compound 153 and 160, which having longer distance at 6-position, provide a way to exam the aceptability of Symplectin. As light emitter in bioluminescent mechanism, coelenteramide analogs (168a-d) were synthesized. It is confirmed that our synthetic analogs have potential to emit luminescence 60~80 nm higher wavelength compared with the natural coelenterazine.