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研究生： 蔡育琳
Tsai, Yu-Lin
論文名稱： 含甜菜鹼修飾基團之兩性離子聚胺酸高分子合成、分子自組裝及應用
Synthesis, Self-assembly and Applications of Zwitterionic Polypeptides Containing Betaine Groups
指導教授： 詹正雄
Jan, Jeng-Shiung
學位類別： 碩士
Master
系所名稱： 工學院 - 化學工程學系
Department of Chemical Engineering
論文出版年： 2016
畢業學年度： 104
語文別： 中文
論文頁數： 195
中文關鍵詞： 聚電解質 、聚胺酸 、雙親性高分子 、抗吸附 、甜菜鹼
外文關鍵詞： polyelectrolyte, polypeptide, zwitterionic polymer, anti-fouling polymer, betaine
相關次數： 點閱：70  下載：2 
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    • 本研究中，利用點擊化學合成方法將小分子甜菜鹼基團接枝於聚胺酸高分子支鏈上，形成聚電解質胺基酸高分子。並探討同聚物聚電解質胺基酸高分子PPLG-g-CB及PPLG-g-SB的核磁共振光譜和紅外光光譜在反應前後的變化，以及不同pH值環境下高分子構象的改變。並也對高分子測定滴定曲線與圓二色光譜作結合，討論彼此的相關性。不同比例嵌段聚胺酸高分子PBLG-b-PPLG及所合成的聚電解質胺基酸高分子除了討論光譜變化外，也針對高分子自組裝所形成的奈米粒子，討論奈米粒子粒徑對環境因素的影響與圓二色光譜和滴定曲線的關聯性，並對奈米粒子的介達電位進行分析。研究中，也將聚電解質嵌段高分子所形成的奈米粒子，以動態粒徑分析儀測定在不同濃度中對蛋白的抗吸附效果作評估。最後，我們也將高分子塗佈於晶圓表面，進行抗汙效果的測試。

    In this work, we reported a novel synthetic route for synthesizing zwitterionic polypeptide derivatives containing azide functionalized carboxybetaine (CB) or sulfobetaine (SB) groups, which two betaine groups are never reported before. These zwitterionic polypeptide derivatives were synthesized by ring-opening polymerization (ROP) of γ-propargyl-L-glyatmate N-carboxyanhydrides and subsequent conjugation of the betaine groups onto the side chains using click chemistry. The as-prepared zwitterionic polypeptide derivatives are expected to exhibit new structures and functions different from the conventional polypeptides. The compositions, molecular weight and characteristic of functional groups of zwitterionic polypeptides were studied by NMR, FT-IR and GPC. The pKa values and chain conformations of these polypeptide derivatives investigated by titration and circular dichroism analyses were found to depend on block ratio, molecular weight, and zwitterionic groups. Zwitterionic, amphiphilic diblock copolypeptide derivatives can form self-assemblies with sizes ranged between 100 and 400 nm based on dynamic light scattering analysis. Zeta potential measurements revealed the charge carried by the self-assemblies depending on solution pH value and betaine groups. Moreover, the protein adsorption on these zwitterionic polypeptides were studied in order to evaluate their use as non-fouling protein/drug encapsulants or carriers.

    目錄 中文摘要 i Extented Abstract ii 誌謝 xv 目錄 xviii 表目錄 xxiii 圖目錄 xxiv 方程式目錄 xxx 附錄目錄 xxxii 第一章 緒論 1 1.1 前言 1 1.2 研究動機 3 1.2.1 奈米材料（Nanomaterial） 3 1.2.2 肽（Peptide） 5 1.2.3 聚胺基酸之特性 6 1.2.4 聚雙性電解質（Polyelectrolyte） 7 1.2.5 點擊化學（Click Chemistry） 8 1.3 研究構想 10 1.3.1 基礎科學研究層面 10 1.3.2 應用開發層面 12 第二章 文獻回顧 13 2.1 胺基酸的聚合 13 2.1.1 NCAs合成 13 2.1.2 NCAs開環聚合 14 2.1.3 聚胺基酸高分子 14 2.2 點擊化學（Click Chemistry） 15 2.3 抗汙高分子（Anti-fouling Polymers） 16 2.4 聚雙性電解質（Polyelectrolyte） 20 第三章 材料與儀器設備 22 3.1 實驗藥品清單 22 3.2 儀器設備清單 24 3.3 分析儀器介紹 25 3.3.1 核磁共振光譜（NMR） 25 3.3.2 動態光散射儀（DLS） 26 3.3.4 介達電位分析儀（Zeta Potential Analyzer） 27 3.3.5 傅立葉轉換紅外光譜（FT-IR） 29 3.3.6 凝膠滲透層析儀（GPC） 31 3.3.7 圓二色光譜（CD） 33 3.3.8 場發射掃描式電子顯微鏡（FE-SEM） 35 3.3.9 穿透式電子顯微鏡（TEM） 37 3.3.10 電位差自動滴定儀（Automatic Potentiometric Titrator） 39 3.3.11 基質輔助雷射解吸/電離飛行時間質譜儀（MALDI-TOF） 40 3.3.12 小角度Ｘ光散射儀（SAXS） 41 3.3.13 接觸角量測儀（Contact Angle Meter） 42 3.3.14 薄膜量測儀（Thin Film Microscope） 43 3.3.15 共軛焦雷射掃描顯微鏡（CLSM） 44 3.4 除水溶劑準備 45 3.4.1 無水四氫呋喃（anhydrous tetrahydrofuran） 45 3.4.2 無水正己烷（anhydrous n-Hexane） 45 3.5 矽晶圓表面處理程序 46 3.5.1 矽晶圓清洗法（RCA Clean） 46 3.5.2 矽晶圓表面矽烷化（Silanization） 47 第四章 實驗步驟 48 4.1 單體的合成 48 4.1.1 合成PLG單體 48 4.2 N-羧酸酐（N-carboxyanhydrides）的合成 49 4.2.1 合成BLG NCAs 49 4.2.2 合成PLG NCAs 50 4.3 同聚物（homo polymer）的合成 51 4.3.1 合成同聚物PPLG20 51 4.3.2 合成同聚物a-PPLG100 51 4.4 嵌段共聚物（block copolymer）的合成 52 4.4.1 合成嵌段共聚物PBLG25-b-PPLG13 52 4.4.2 合成嵌段共聚物PBLG13-b-PPLG25 53 4.5 雙性電解質基團（zwitterionic moieties）的合成 54 4.5.1 合成3-Dimethylamino-1-propyl azide 54 4.5.2 合成羧基甜菜鹼（Carboxybetaine） 55 4.5.3 合成磺基甜菜鹼（Sulfobetaine） 55 4.6 聚電解質胺基酸高分子的合成 56 4.6.1 合成聚電解質胺基酸高分子PPLG20-g-CB 56 4.6.2 合成聚電解質胺基酸高分子PPLG20-g-SB 57 4.6.3 合成聚電解質胺基酸高分子a-PPLG100-g-CB 58 4.6.4 合成聚電解質胺基酸高分子a-PPLG100-g-SB 59 4.6.5 合成聚電解質胺基酸高分子PBLG25-b-PPLG13-g-CB 60 4.6.6 合成聚電解質胺基酸高分子PBLG25-b-PPLG13-g-SB 61 4.6.7 合成聚電解質胺基酸高分子PBLG13-b-PPLG25-g-CB 62 4.6.8 合成聚電解質胺基酸高分子PBLG13-b-PPLG25-g-SB 63 第五章 結果與討論 64 5.1 胺基酸單體、雙性分子及聚電解質高分子的合成與探討 66 5.1.1 類胺基酸單體PLG及雙性分子CB、SB的合成與探討 66 5.1.2 聚電解質高分子PPLG20-g-CB及PPLG20-g-SB的合成與探討 71 5.1.3 聚電解質高分子PBLG25-b-PPLG13-g-CB及PBLG25-b-PPLG13-g-SB的合成與探討 79 5.1.4 聚電解質高分子PBLG13-b-PPLG25-g-CB及PBLG13-b-PPLG25-g-SB的合成與探討 92 5.1.5 聚電解質高分子的綜合比較 106 5.2 探討高分子自組裝奈米粒子之抗汙特性 110 5.2.1 以BSA蛋白檢測高分子奈米粒子抗吸附能力 111 5.2.2 以Mb蛋白檢測高分子奈米粒子抗吸附能力 111 5.2.3 以LYZ蛋白檢測高分子奈米粒子抗吸附能力 112 5.2.4 聚電解質高分子抗吸附能力總述 114 5.3 探討矽晶圓表面接枝聚電解質高分子之製程及抗汙特性 115 5.3.1 矽晶圓表面洗淨、電漿氧化及矽烷化過程 115 5.3.2 利用硫醇-烯基點擊化學反應接枝聚電解質高分子 118 5.3.3 矽晶圓接枝聚電解質高分子之抗汙特性討論 122 第六章 結論 128 第七章 未來研究 130 第八章 參考文獻 132 附 錄 147 履歷表 CURRICULUM VITAE 195

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