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標題: | 氟化學以及點擊化學在合成策略上的探討 Investigations on the synthetic strategies utilizing fluorous chemistry and click chemistry |
作者: | Miao-Ru Kang 康妙如 |
指導教授: | 羅禮強(Lee-Chiang Lo) |
關鍵字: | 氟相標籤,環酯肽,葉酸衍生物,原紫質,金屬紫質,點擊化學, fluorous tag,cyclic depsipeptides,folic acid derivatives,protoporphyrin,metal-protoporphyrin,click reaction., |
出版年 : | 2020 |
學位: | 碩士 |
摘要: | 化學反應都須考慮到溶解度、選擇性和後續反應混合物的純化問題,因此在過去的許多合成策略中,都以此為出發點進行改良與探討。在本論文中,也有效應用氟化學及點擊化學去解決合成中所遇到的困境。 第一部份利用氟化學的特性,我們致力於新型氟相標記物的開發,成功合成兩種不同的氟相標記物,分別為單條氟鏈的苯甲基硫醇,及具對稱性的雙氟鏈苯甲基硫醇。並且將雙氟鏈氟相標記物應用於環酯肽的合成,同時也合成雙酯肽作為建構單元,以利後續實驗的進行及實驗條件上的優化。藉此驗證其在胜肽合成上的可應用性。 第二部份是利用點擊化學合成葉酸衍生物,葉酸已在成像、診斷和癌症治療等領域進行了廣泛的研究。但是,葉酸的結合常受到其獨特的溶解性和選擇性的限制。所以將葉酸修飾上環辛炔的結構,然後將功能性分子的部分修飾成疊氮化合物。在本論文中成功合成葉酸-BCN化合物,及原紫質、鋅紫質及鈷紫質的疊氮化合物。最後再以點擊化學的方式將兩個片段進行結合,也預期此合成策略可以有效解決具有相同性質之衍生物合成。 Chemical reactions must take into account the solubility, selectivity, and purification of reaction mixture. In the past, there are many synthetic strategies that used these factors as a starting point for improvement and discussion. In this thesis, fluorous chemistry and click chemistry are effectively applied to solve the dilemma encountered in the current synthesis. In the first part, we devoted to the development of new fluorous tags by using the characteristics of fluorous chemistry. Herein, two different fluorous tags are successfully synthesized, which are mono-fluorous thiol and symmetrical di-flourous thiol. In addition, the di-flourous thiol is applied to the synthesis of cyclodepsipeptide. At the same time, the depsipeptide is also synthesized as a building block to facilitate subsequent experiments and optimize the experimental conditions, to demonstrate the potential of this methodology in peptide synthesis. The second part is the synthesis of folic acid derivatives using click chemistry. Folic acid has been extensively studied in the field of imaging or diagnosis and the treatment of cancers. However, conjugation of folic acid is limited by its unique solubility and selectivity issues. Herein is provided a small folic acid conjugate with cyclooctyne, and the functional molecule is derived as an azide compound. In this thesis, we successfully synthesized folate-BCN conjugate, protoporphyrin, zinc protoporphyrin and cobalt protoporphyrin bearing azide. Finally, two molecules are conjugated by click reaction. It is also expected that this synthetic strategy can effectively solve the synthesis of derivatives with the same properties. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/53629 |
DOI: | 10.6342/NTU202002413 |
全文授權: | 有償授權 |
顯示於系所單位: | 化學系 |
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