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系統識別號 U0026-1201201700464900
論文名稱(中文) 發展以離子液體為基材之固相合成法來製備細菌細胞壁之肽聚醣類分子
論文名稱(英文) Ionic Liquid-Supported Synthesis of Bacterial Peptidoglycan Analogues
校院名稱 成功大學
系所名稱(中) 化學系
系所名稱(英) Department of Chemistry
學年度 104
學期 2
出版年 105
研究生(中文) 徐崇桓
研究生(英文) Chung-Huan Hsu
學號 L36031097
學位類別 碩士
語文別 英文
論文頁數 167頁
口試委員 指導教授-鄭偉杰
共同指導教授-周鶴軒
召集委員-俞聖法
口試委員-楊文彬
中文關鍵字 離子液體  細菌細胞壁  肽聚醣類似物  磷酸化  醣基化 
英文關鍵字 Ionic Liquid  Bacterial Cell Wall  Peptidoglycan Analogues  Phosphorylation  Glycosylation 
學科別分類
中文摘要 細菌細胞壁是維持細菌細胞的形狀以及對抗滲透壓重要的結構,而其組成成分為肽聚醣,在肽聚醣中有著許多獨特且結構複雜的生物分子,這些分子富含生物應用的潛力,像是對抗細菌或是自體免疫的研究。然而,現在由天然物純化得到這些分子或是再直接對這些分子修飾結構仍有困難。因此,就化學家而言,發展新的方法對於收集或製備有系統的肽聚醣類分子是很重要的任務。在這份論文中,分為三個部分來研究:(a) 開發藉由離子液體基材的固相合成法來製備含磷官能基的肽聚醣分子之合成路徑,(b) 開發藉由離子液體基材的固相合成法來製備肽聚醣分子中的糖鏈結構之合成路徑,(c) 離子液體基材的發展。經由我們的努力,我們成功展示了新的離子液體基材,在於合成上,這些新基材將可帶來更加便利的應用。除此之外,我們成功發展了以離子液體基材的固相合成法來製備含磷中間物的合成路徑,對於製備含有焦磷酸官能基的肽聚醣前驅物而言,這是個關鍵的中間物。再加上我們找到適當的以離子液體基材的固相合成法來進行醣基化反應的適當條件,這對於使用離子液體來建構肽聚醣前驅物分子中的糖鏈是一大進展。我們相信由這份研究中所得到的結果,藉由離子液體基材的固相合成法可以加快合成肽聚醣前驅物分子的進度。
英文摘要 In the bacterial peptidoglycan (PGN), there are lots of unique and structurally complex biologically interesting molecules. However, it is still difficult to purify them from natural sources and directly modify them from these isolated molecules.
Thus, development of new methods for preparation structurally diverse PGN analogues is an important task to chemists. In this work, there are three parts: (a) development of IL-supported synthetic routes for preparation of peptidoglycans with a phosphate moiety (b) discovery of IL-supported synthesis for preparation of glycan chains of PGN, (c) development of ionic liquid matrixes. Through our efforts, we have we have successfully developed two methods to prepared the IL-supported intermediate bearing a phosphate at the reducing end of saccharides. It is a pivotal intermediate that allows us for further construction of a pyrophosphate synthesis. In addition, we have demonstrated new IL-matrixes, which might be more convenient for IL-supported synthesis. We believe our developed conditions can accelerate the progress of IL-supported peptidoglycan synthesis in the future.
論文目次 Contents
中文摘要........ I
Abstract........II
誌謝........III
Contents........IV
Index of Figures........V
Index of Tables........VI
Index of Schemes........VII
Abbreviations........VIII
Chapter 1 . Introduction........1
1.1 Introduction of bacterial peptidoglycan........1
1.2 Biosynthesis of bacterial cell wall........2
1.3 Previous work in our laboratory........3
1.4 Matrix-supported synthesis of PGN fragments........3
1.5 IL-support synthesis of PGN fragments........5
1.6 Motivation........6
Chapter 2 . Results and Discussion........7
2.1. Development of IL-supported synthetic routes for preparation of peptidoglycans with a phosphate moiety........7
2.2. Discovery of IL-supported synthesis for preparation of glycan chains........20
2.3 Developing new ionic liquid matrix........24
2.4 Future work........32
2.5 Conclusions........36
Chapter 3 . Experimental Section........37
3.1 General experimental procedure........37
3.2 Procedures and experimental data........38
References........81
Appendix........86
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