方俊民臺灣大學：化學研究所趙庭榕Chao, Ting-JungTing-JungChao2007-11-262018-07-102007-11-262018-07-102004http://ntur.lib.ntu.edu.tw//handle/246246/51941醣在細胞的辨識方面扮演很重要的角色，所以有釵h需要研究其分子辨識的方法；醣含有釵h的羥基，因此可以用含氫鍵，或是含有可以用共價鍵鍵結的受體去辨識。 本論文中，合成化合物16，是將化合物15與2-甲醯苯硼酸用還原胺化法而得到；其含有硼酸部分，可以與醣類分子以共價鍵鍵結。將化合物15、16拿去與醣類分子作滴定實驗（分別為D-葡萄糖辛烷苷、D-甘露糖辛烷苷與D-果糖辛烷苷），結果為化合物15沒有明顯的變化，而化合物16則表現了吸收紅移與螢光淬滅。由此，可能是這些醣類分子像甲醇會與硼酸作用，而減弱對苯胺上電子的束縛，使較有效去與naphthyridine部分產生電荷分離的效果，造成吸收紅移與螢光減弱。 本論文其他的研究，是討論二碘化釤對吡咯環上氮保護基的反應；發現會使得其保護基離開而得到起始化合物25。Sugars play important roles in cell recognition. For this reason, there are many ways have been developed for molecular recognition of sugars. As a sugar molecule contains polyhydroxyl groups, one can use an appropriate receptor to catch the sugar molecular via hydrogen bondings or covalent interactions. In this thesis, a reductive amination was used to prepare compound 16 with the boronic acid moiety. The moiety can provide covalent interaction with sugars. The titration experiments of compound 15 and compound 16 with sugars were carried out. Compound 15 didn’t have obvious change, but compound 16 showed the red shift absorption and decreased fluorescence on titration with sugars. When a sugar molecule binds with the boronic acid moiety of compound 16, the aniline moiety would be released to cause intramolecular charge transfer, and thus contributes to the spectral change. In the other part of this thesis, the reaction SmI2 with N-protected pyrroles was investigated. The result showed the protecting group will leave by reduction of SmI2 to get the unprotected compound 25.圖目錄…………………………………………………………….. Ⅰ 表目錄…………………………………………………………….. Ⅲ 簡稱用語對照表………………………………………………….. Ⅳ 中文摘要………………………………………………………….. Ⅵ 英文摘要………………………………………………………….. Ⅶ 壹、緒論………………………………………………………….. 1 1-1分子辨識…………………………………………………… 1 1-2醣類分子辨識……………………………………………… 4 1-3硼酸類分子在分子辨識上的表現………………………… 8 1-4小結論……………………………………………………… 18 貳、結果與討論…………………………………………………… 19 2-1-1以苯甲基胺化合物與硼酸架構的醣類分子受體………. 19 2-1-2分子受體的設計與合成…………………………………. 22 2-1-3小結論……………………………………………………. 25 2-2-1以苯胺化合物與硼酸架構的醣類分子受體……………. 26 2-2-2分子受體的合成…………………………………………. 26 2-2-3測試實驗結果與討論……………………………………. 29 2-2-4 與文獻的比較…………………………………………... 40 2-2-5小結論……………………………………………………. 42 參、結語…………………………………………………………… 43 肆、其他研究…………………………………………………….. 44 2-吡咯甲酸甲酯與酮類三成分聯繼性偶合反應之研究………...44 4-1前言………………………………………………………… 44 4-2實驗計畫…………………………………………………… 45 4-3實驗結果與實驗討論……………………………………… 46 4-4氮上保護基的去保護……………………………………… 51 4-5結論………………………………………………………… 52 伍、實驗部分……………………………………………………… 54 陸、參考文獻……………………………………………………… 81 柒、附錄…………………………………………………………… 872546721 bytesapplication/pdfen-US硼酸分子受體胺aminereceptorboronic acidthesishttp://ntur.lib.ntu.edu.tw/bitstream/246246/51941/1/ntu-93-R91223044-1.pdf