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研究生:邱玉瑩
論文名稱:在N,N-二甲基乙醯胺溶液中,以對-苯酉昆和咪唑利用加成反應偶合形成ATP之研究
論文名稱(外文):Study on the ATP Producton Coupled to the Addition Reaction Betwwen p-Benzoquione and Imidazole in N,N-dimethylacetamide
指導教授:黃坤博
學位類別:碩士
校院名稱:中原大學
系所名稱:化學學系
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:1997
畢業學年度:85
語文別:中文
論文頁數:48
中文關鍵詞:模擬化學共軛鹽類
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本篇的主要目的是欲利用生物模擬化學(Biomimetic Chemistry)的方式探討ATP在生物系統下尚無法詳細討論的反應機制。我們選定具有類似胜月太結構的N,N-二甲基乙醯胺(N,N-Dimethylacetamide,DMAC)為非水溶劑,並利用對-苯酉昆(p-Benzoquinone)及咪唑(Imidazole)的加成反應所產生的物質來推動ADP和無機磷根作用,使其產生較高能量的ATP。
為有效的分離和分析有關之AMP,ADP和ATP,找出最適當分離條件;本研究利用離子交換樹脂,以適當濃度的甲酸及其共軛鹽類(甲酸銨)為沖提液,採用階級梯度(Step-gradient)的方式,將AMP,ADP,ATP等樣品進行分離和純化,最後再以紫外光-可見光光度計(UV/Visiable Spectra-photometer)做定量的工作。在甲酸條件下,AMP,ADP和ATP的回收率高達97%以上,相較以往所知的90%之回收率有所改進,分離度也有很大的改進。
本研究的結論是在上述化學反應條件下,將At)PP和無機磷酸根在MMAC中脫水形成ATP之重要條件為─酉昆及咪唑之加成反應產物變成半苯酉昆後,行一電子還原,還原ADP之腺嘌呤環,以增加其胺基的鹼性,使其能吸附無機磷酸根,再把無機磷酸接上同分子內之焦磷酸根而形成ATP。
從理論上的檢討,作者相信ADP之立體構造是呈折疊型,此構造可使無機磷酸根在同分子內接上ADP之焦磷酸根,以形成ATP。這論點也可從AMP形成ADP之速率和ADP形成ATP之速率之比較而獲得支持。
In a non-aqueous medium, ATP formation was observed from ADP and inorganic phosphate anion by coupling with the reaction between p- benzoquinone and imidazole. The purpose of this study is to investigate the essential mechanism of phosphorytation reaction. Furthermore, in order to clarity the reaction, efforts were also made to find out the optimum analytical conditions for the separation and quantitization of AMP, ADP and ATP during the reaction process.
First of all, in the reaction system, p-benzoquinone and imidazole were found to produce an addition compound, 2-imidazoly1 hydroquin-one. This compound was then oxidized readily by aerobic oxygen or by unreacted p-benzoquinone, and produced 2-imidazoly1 semiquinone anion radicals in DMAC. Naturally p-benzosemiquinone anion radical was also present in the latter case. However in other less polar, less basic non-aqueous solvents, such as THF and acetonitrile, insoluble quinhydrone-type product between the two rather than two kinds anion radicals was observed when excess p-benzoquinone was present in the system.
2-Imidazoly1 semibenzoquinone anion radical which absorbed at 468nm was found as a strong one-electron reducing agent, capable of reducing the adenine ring of ADP, which in turn, could increase the basicity of the amino group in the ring to such an extent that the inorg- anic phosphate was attracted by the group. This phosphate group could be transferred to the terminal pyrophosphate group of ADP during a dehydration process and produced ATP.
Theoretical consideration as well as kinetic studies by comparing AMP- and ADP-containing system in the phosphorylation reaction has strongly suggested that, ADP in a natural condition has a folded confor- mational arrangement which makes ADP to be a better phosphate-accept- or than AMP.

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