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| 研究生： |
范姜銘威 Jiang, Ming-Wei Fan |
|---|---|
| 論文名稱： |
綠色螢光蛋白發光團之對位三級胺取代的合成、光/熱異構化反應、水解反應及光物理性質之探討 para-N,N,N-Trimethylbenzenaminium Chromophore of Green Fluorescent Protein: Synthesis, Photo/Thermal Isomerization, Hydrolysis and Photophysical Properties |
| 指導教授： |
宋光生
Sung, Kuang-Sen |
| 學位類別： |
碩士 Master |
| 系所名稱： |
理學院 - 化學系 Department of Chemistry |
| 論文出版年： | 2017 |
| 畢業學年度： | 105 |
| 語文別： | 中文 |
| 論文頁數： | 53 |
| 中文關鍵詞： | 綠色螢光蛋白類似物 、酸性水解反應 |
| 外文關鍵詞： | GFP, p-HBDI, protonation, acidic condition, hydrolysis |
| 相關次數： | 點閱：111 下載：0 |
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近年來已有許多綠色螢光蛋白的相關研究，部分研究表示綠色螢光蛋白在酸性環境下會變性，但都是取自天然的GFP模型直接與酸進行作用，顯少有研究指出p-HBDI在酸性作用下，致使其變性的機制及變性結果。我們的策略則是合成出p-HBDI類似物，利用甲基化的方法模擬質子化，以進行模擬p-HBDI在酸性環境下受到質子化後的效果。我們合成出的p-HBDI類似物n3-Bn和n4-Bn，發現甲基化後五元雜環上的amidine碳 (C7)變得較缺電子，更易受到親核基的攻擊而導致水解。此外，化合物照射波長350 nm之光源後，藉由追蹤核磁共振儀積分值比例得知光異構化轉換率，並利用sigma-plot軟體計算出熱異構化速率常數，另外，我們也使用核磁共振儀與UV-vis來觀察p-HBDI類似物在模擬酸性環境下的變化結果，並且測量吸收、螢光放射光來探討其光物理性質。
To identify p-HBDI under the acidic condition, we used methylation method to simulate the protonated type of p-HBDI. We synthesize GFP chromophoric analogues n3-Bn and the methylation form of n3-Bn (n4-Bn). To discuss the property of photoisomerization, this two compounds was excited by UV lamp with 350nm wavelength. Furthermore, we used the integration of 1H-NMR to calculated the rate of thermal isomerization. To compare compounds n3-Bn and n4-Bn, we found that protic solvent or water could easily affected compound n4-Bn. Due to the positively charged nitrogen on n4-Bn,the amidine carbon on five-membered heterocyclic ring became electron deficient and it was attacked by nucleophile such as H2O. Moreover, we used 1H-NMR spectrum and the integration of 1H-NMR to calculated the rate of hydrolysis. These result could further to identify the fate of p-HBDI under the acidic condition.
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校內：2021-07-01公開校外：不公開