理學院: 化學研究所指導教授: 王宗興何聲揚Ho, Sheng-YangSheng-YangHo2017-03-022018-07-102017-03-022018-07-102016http://ntur.lib.ntu.edu.tw//handle/246246/271939Dickeya dadantii 和 Pectobacterium carotovorum 是造成細菌性植物軟腐病最主要的兩株病菌，他們的宿主涵蓋大多數的經濟作物諸如蔬果與花卉，每年在全球造成嚴重的經濟損失，然而，截至今日仍未有有效的藥物可用來對抗此種疾病。 在軟腐病的感染期間，這些病菌會分泌一些小分子的鐵螯合劑-鐵載體，用以從宿主體內獲取鐵分子。鐵載體具有能夠將鐵從細菌外帶進細菌內的特性，因此提供一個適合拿來做為特洛伊木馬的策略，在運送鐵的同時將藥物一併帶進細菌體內。這兩種軟腐病菌皆以菊菌素(chrysobactin)作為他們共同的鐵載體。菊菌素相較於其他細菌鐵載體而言對鐵的螯合力相當弱，其如何與受體結合，仍未充分地被研究。 此篇碩士論文中，藉由有機合成，合出不同的菊菌素衍生物來研究鐵載體與其受體之間的構效關係。另外，近期被新發現的環形三聚菊菌素(cyclic tri-chrysobactin)在此報告中首次被化學全合成出，此環形三聚菊菌素與電腦模擬出的三菊菌素錯合物有極為相似的結構，然而初步測試結果其衍生物只能被分泌此環形三聚菊菌素的菌種所使用，是否有專門的受體負責辨識此新型鐵載體仍需要進一步研究。  Dickeya dadantii and Pectobacterium carotovorum are the two major plant pathogens which cause soft rot disease on a wide variety of economic important vegetables and ornamental corps around the globe. The losses cause by this kind of disease is tremendous every year. Still, there is currently no effective chemical agent against this disease. During the infection period, these soft rot bacteria secrete a small molecule iron chelator termed siderophore to scavenge iron from its host. The ability of siderophore to shuttle iron into cytoplasm of bacteria provides an ideal pathway for the Trojan horse design of siderophore-drug conjugate. The main siderophore of these soft rot bacteria – chrysobactin is a relatively weak iron chelator compared with other siderophore system. Its iron complex-receptor interaction has not been well studied. In this work we synthesized a series of chrysobactin analogues in order to study the structure-activity relationship of the chrysobactin iron complex. A new siderophore, cyclic tri-chrysobactin, reported in 2011 was also synthesized in this work. It is the cyclic form of three chrysobactin linked by ester bonds. The highly resemblance between this cyclic trimer and computational modeling of tris(chrysobactin) complex make us wonder the stoichiometric ratio of the biologically active chrysobactin complex. By chemical engineering of the trimeric chrysobactin, we successfully deliver the trimeric conjugates into its native producer, but not those who use chrysobactin. The implication of a new receptor responsible for cyclic trimer still needs to be confirmed in the future.12044847 bytesapplication/pdf論文公開時間: 2017/9/14論文使用權限: 同意有償授權(權利金給回饋學校)軟腐病鐵載體soft rot diseasechrysobactinsiderophorethesis10.6342/NTU201602866http://ntur.lib.ntu.edu.tw/bitstream/246246/271939/1/ntu-105-R03223179-1.pdf