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    Title: 生物晶片基材表面修飾分子之合成研究
    Other Titles: Synthesis of modified anchoring molecules for biochip substrate
    Authors: 謝信賢;Hsieh, Hsin-Hsien
    Contributors: 淡江大學化學學系碩士班
    李世元;Lee, Adam Shih-Yuan
    Keywords: 生物晶片;自我組裝單層膜;有機硫醇化合物;Bithiophene;Biochip;SAMs
    Date: 2015
    Issue Date: 2016-01-22 14:52:12 (UTC+8)
    Abstract: 有機化合物之硫醇官能基能與金金屬反應生成共價鍵,在金表面會進行自發性排列,形成自我組裝單層膜( Self-Assembled Monolayer,SAM )。利用此一SAM特性,此類有機硫醇化合物被廣泛應用於生物晶片( Biochip )的研究。
    由於蛋白質為胺基酸的聚合物,所以用來偵測蛋白質的最佳反應分子即本身具有可參與反應的胺基( -NH2 )或羧酸基( -CO2H )。因此,我們使用具有絕佳導電性之2,2’-雙噻吩分子作為主要結構,再將其一端修飾上具有可與胺基酸分子參與反應之羧酸官能基;而另一端則接上硫醇官能基,因此設計可與待檢測生物分子作用且能與生物晶片表面穩定鍵結之單體分子( Linker ) A與B。
    本研究主要探討利用硫醇官能基的保護與去保護反應策略合成下列兩種硫醇目標化合物。目標化合物A利用新丁烷基( -tBu )對硫醇官能基進行保護後,再與經溴化之2,2’-雙噻吩分子進行Suzuki耦合反應而合成。目標化合物B則是利用雙硫鍵作為對苯胺分子4-位置硫醇官能基之保護機制,再與2,2’-雙噻吩的5-位置之羧酸官能基進行反應而合成。
    Our laboratory has developed and reported a series of thiophene-based compounds which were synthesized and employed as biolinkers of biochip. Due to π-electron conjugation property of mutiple thiophene rings, bis-thiophene-based compounds display planar structure and conjugation which possess some great electron conductivity. The introduction of thiol functionality on thiophene can provide the covalent bond on gold metal surface to generate Self-Assembled Monolayer (SAM) by a spontaneously chemical reaction. This SAM can improve the detection sensitivity when it was introduced on the biochip application.
    Therefore, we synthesized two kinds of mercapto-bis-thiophene-based molecules, and also modified carboxylic acid group on another terminal site of thiophene ring.
    These new organic compounds may be able to apply on the biochip research and act as the linkers between substrate and detecting probe.
    Appears in Collections:[化學學系暨研究所] 學位論文

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