博碩士論文 92223011 詳細資訊




以作者查詢圖書館館藏 以作者查詢臺灣博碩士 以作者查詢全國書目 勘誤回報 、線上人數:20 、訪客IP:3.231.229.89
姓名 吳斯燻(Szu-Hsun Wu)  查詢紙本館藏   畢業系所 化學學系
論文名稱 以毛細管電泳法計算主-客內包錯合物結合常數之研究
(Application of cyclodextrin-mediated capillary electrophoresis to determine the apparent binding constants and of the alkylnaphthalene derivatives)
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摘要(中) 毛細管電泳層析術提供了極高效率的分離度,且分析速度快、以及具有分析少量樣品和溶劑消耗量少的特性,並且可以使用多種分離模式針對大部分的物質進行電泳分離。藉由添加一種具有空腔結構的主分子與分析物 (客分子)錯合形成非共價鍵錯合物(non-covalent bond complex),而形成非共價鍵結構的主-客錯合物(host-guest complexes)或稱為內包錯合物(inclusion complexes),進而影響內包錯合物之電泳遷移率,以達到結構異構物及藥物之光學異構物分離(chiral separation)。毛細管電泳的應用於生物分子辨識 (molecular recognition)之研究多用來鑑定抗原-抗體或受質(ligand)-受器(receptor)間之作用力的專一性,藉由簡化的主-客模型來預測複雜的自然生物行為,而毛細管電泳不僅可從事這些作用力的定性分析研究,同時亦適合於定量上的探討。
在適當的條件下,毛細管環糊精修飾區帶電泳法 (cyclodextrin electrokinetic chromatography, CD-EKC)能有效分離七種中性烷基?環分子位置異構物,分離的最佳條件是在緩衝溶液中添加carboxymethyl-?-cyclodextrin (CM-?-CD),在pH 6.0的情況下,達到最佳的分離效果。藉由結合常數的計算可以了解中性烷基?環分子與CM-?-CD的錯合模式 (1:1或2:1化學計量內包錯合物),並搭配光譜技術,以證實毛細管電泳法所計算之結合常數與傳統光譜法計算結果之一致性。中性烷基?環分子在?位置上取代的異構物,如1-ethylnaphthalene, 1,4-dimethylnaphthalene兩種中性?環異構物,會與兩個CM-?-CD錯合形成2:1化學計量之主-客內包錯合物。藉由溫度的改變可以得知CM-?-CD與中性烷基?環分子在不同溫度下的結合常數變化,以計算主-客錯合作用的熱力學參數。CM-?-CD與中性烷基?環分子在?位置上之?S為正值,驗證CM-?-CD與?環?位置上的中性烷基?環分子錯合機制,在任何溫度下都可自發性的產生,且低溫下有較佳的錯合作用。
摘要(英) Capillary electrophoresis (CE) has been established as a powerful technique for separating an unusually large variety of compounds. This versatility is due in part to the ease and speed with which the CE running buffer can be altered with a variety of reagents to influence the migration rates. And CDs were commonly used host molecules. The family of cyclodextrins (CDs) is one of the most intensively studied macromolecular systems. The formation of cyclodextrin-based guest-host complexes is a simple model for studying molecular recognition processes, and has been employed in many applications, such as pharmaceutical, cosmetic and food industries.
The separation and migration behavior of seven positional and structural neutral alkylnaphthalene derivatives in cyclodextrin-mediated electrokinetic chromatography were systematically investigated. The effective separation conditions were to use 10 mM phosphate buffer with negatively charged carboxymethyl-?-cyclodextrin (CM-?-CD) at pH 6.0. The guest-host interactions with both 1:1 and 1:2 binding stoichiometries for various derivatives have been evaluated by comparing the apparent binding constants, the results reveal that the substituent group(s) attached to the naphthalene ring significantly affected the inclusion stoichiometric behaviors. Alkylnaphthalene derivatives with the substituent(s) at 1-position(s), such as 1-ethylnaphthalene, 1,4-dimethylnaphthalene, may undergo complexation with one and two CM-?-CD molecules. The binding constants of these derivatives agreed closely with the data obtained by a photometric method. The thermodynamic parameters were also calculated to improve our understanding of the interaction between the neutral alkylnaphthalene derivatives and CM-?-CD at various temperatures. The positive entropy (?S?) values for the alkylnaphthalenes with the substituent(s) at 2-position(s) indicate that the inclusion of the guest molecule into the cavity of CM-?-CD is favored at all temperatures.
關鍵字(中) ★ 環糊精
★ 毛細管電泳法
★ 結合常數
★ 熱力學
關鍵字(英) ★ Inclusion complex
★ Cyclodextrins
★ Thermodynamic parameters
★ Apparent binding constants
論文目次 目錄
中文摘要 ---------------------------------------------------------------- Ⅰ
英文摘要 ---------------------------------------------------------------- Ⅲ
目錄 -------------------------------------------------------------------- VI
表目錄------------------------------------------------------------------- X
圖目錄 --------------------------------------------------------------- XI
第一章 前言 -------------------------------------------------------------- 1
1-1 研究的緣起 ----------------------------------------------------------- 1
1-2 研究目標 ------------------------------------------------------------- 2
第二章 文獻回顧 ---------------------------------------------------------- 6
2-1 毛細管電泳的歷史背景和發展 ------------------------------------------- 6
2-2 毛細管電泳分離原理 --------------------------------------------------- 9
2-2-1 電滲流 ------------------------------------------------------------- 9
2-2-2 電泳移動速率 ------------------------------------------------------- 14
2-3 毛細管電泳的分離模式 ------------------------------------------------- 15
2-4 主-客錯合現象 -------------------------------------------------------- 17
2-4-1環糊精 -------------------------------------------------------------- 18
2-4-2 衍生環糊精 ----------------------------------------------------- 19
2-4-3 內包錯合物 ----------------------------------------------------- 26
2-5 主-客分子之錯合作用 -------------------------------------------------- 29
2-5-1 毛細管電泳法計算結合常數 --------------------------------------- 29
2-5-2 光譜法及酵素動力學之結合常數計算 ------------------------------- 34
2-5-3 黏滯力與電雙層作用力對計算的影響 ------------------------------- 38
2-5-4 溶液中離子強度對計算的影響 ----------------------------------- 40
2-5-5 協作效應 ----------------------------------------------------- 43
2-5-6 環糊精與對掌型異構物錯合之熱力學常數計算之探討 --------------- 47
第三章 實驗步驟與樣品分析 ------------------------------------------------ 49
3-1 實驗藥品與儀器設備 --------------------------------------------------- 49
3-1-1實驗藥品 ------------------------------------------------------------ 49
3-1-2 儀器設備 -------------------------------------------------- 51
3-2 實驗步驟 ------------------------------------------------------------- 53
3-2-1烷基?環異構物之分析------------------------------------------------- 53
3-2-1.1 標準品的製備 ---------------------------------------------------- 53
3-2-1.2 緩衝溶液的製備 -------------------------------------------------- 53
3-2-1.3 毛細管的處理 ----------------------------------------------------- 53
3-2-1.4 實驗操作條件 ----------------------------------------------------- 55
第四章 結果與討論 -------------------------------------------------------- 56
4-1離子性環糊精對烷基?環分子結構異構物分離影響 -------------------------- 56
4-1-1添加環糊精分離中性?環分子 ------------------------------------------ 56
4-1-2 緩衝溶液之pH及緩衝溶液濃度對分離的影響 ----------------------------- 60
4-2 結合常數之計算 ------------------------------------------------------- 63
4-2-1黏滯力作用因子的校正 ------------------------------------------------ 63
4-2-2線性及非線性方程式計算結合常數 -------------------------------------- 67
4-2-3以1:1 化學計量結合常數之結果 --------------------------------------- 68
4-2-3.1單一甲基烷基?環異構物 -------------------------------------------- 68
4-2-3.2單一乙基烷基?環異構物 -------------------------------------------- 69
4-2-3.3雙甲基烷基?環異構物 ---------------------------------------------- 71
4-2-3.4光譜法與毛細管電泳法之比較 ---------------------------------------- 72
4-2-4 以1:1及1:2 化學計量結合常數 -------------------------------------- 75
4-2-4.1 單一甲基烷基?環異構物 ------------------------------------------- 75
4-2-4.2 單一乙基烷基?環異構物 ------------------------------------------- 76
4-2-4.3 雙甲基烷基?環異構物 --------------------------------------------- 77
4-3 協作效應對計算結合常數之影響 ----------------------------------------- 81
4-3-1 利用三組線性方程式以判斷主-客內包錯合物之錯合模式 ------------------ 81
4-3-1.1 以y-reciprocal方程式觀察高階錯合之現象 --------------------------- 81
4-3-1.2 以double-reciprocal方程式觀察高階錯合之現象 ---------------------- 84
4-3-1.3 以x-reciprocal方程式觀察高階錯合之現象 --------------------------- 86
4-3-2環糊精濃度對結合常數之影響 ------------------------------------------ 88
4-4 環糊精與中性烷基?環分子錯合之熱力學常數計算 ------------------------ 90
第五章 結論 -------------------------------------------------------------- 95
參考文獻 ----------------------------------------------------------------- 97
附錄 --------------------------------------------------------------------- 106
A-1以非線性及線性方程式以計算不同溫度下,甲基取代?環分

子的結合常數及內包錯合物之電泳遷移 -------------------------------------- 106
A-2以非線性及線性方程式以計算不同溫度下,乙基取代?環分

子的結合常數及內包錯合物之電泳遷移 -------------------------------------- 108
A-3以非線性及線性方程式以計算不同溫度下,雙甲基取代?環

分子的結合常數及內包錯合物之電泳遷移 ------------------------------------ 110
B-1不同濃度之CM-?-CD添加至0.04 mM 1-MeNap分子,UV光
譜圖的變化情形 ---------------------------------------------------------- 112
B-2不同濃度之CM-?-CD添加至0.04 mM 2-MeNap分子,UV光
譜圖的變化情形 ---------------------------------------------------------- 112
B-3不同濃度之CM-?-CD添加至0.04 mM 1-EtNap分子,UV光譜
圖的變化情形 ------------------------------------------------------------ 113
B-4不同濃度之CM-?-CD添加至0.04 mM 2-EtNap分子,
UV光譜圖的變化情形 ------------------------------------------------------ 113
B-5不同濃度之CM-?-CD添加至0.04 mM 1,4-DMNap分子,UV光譜圖的變化情形 ---- 114
B-6不同濃度之CM-?-CD添加至0.04 mM 1,5-DMNap分子,UV光譜圖的變化情形 ---- 114
B-7不同濃度之CM-?-CD添加至0.04 mM 2,6-DMNap分子,UV光譜圖的變化情形 ---- 115
表目錄
表1-1. 烷基?環分子之結構式,縮寫及其波峰之符號代號 ---------------------- 5
表2-1. 環糊精的性質 ------------------------------------------------------ 23
表2-2. 衍生環糊精的種類及其取代基的位置 ---------------------------------- 25
表2-3. 毛細管電泳法中計算結合常數的公式 ---------------------------------- 37
表3-2. 光譜法及毛細管電泳法計算結合常數的公式 ---------------------------- 37
表3-1. 毛細管電泳儀(CE)設定參數 ---------------------------------------- 55
表4-1. CM-?-CD的黏滯力較正因子 ------------------------------------------ 65
表4-2. 四種非線性及線性方程式所計算的結合常數及經黏滯力校正之後的結合常數- 66
表4-3. 1:1及1:1與1:2化學計量內包錯合物之結合常數及電泳遷移率 ---------- 74
表4-4. Hamai et al.與本研究使用毛細管電泳所計算的結合常數之比較 ---------- 80
表4-5. 六種不同溫度下CM-?-CD與烷基?環分子之結合常數--------------------- 93
表4-6. CM-?-環糊精與?之位置異構物錯合之熱力學參數 ---------------------- 94
圖目錄
圖2-1. 毛細管內壁之Stern電雙層模型 --------------------------------------- 10
圖2-2. 毛細管內之電位變化圖 ---------------------------------------------- 11
圖2-3. 流體流動剖面圖 ---------------------------------------------------- 13
圖2-4. 環糊精的種類 ------------------------------------------------------ 24
圖2-5 ?-CD與1-hydroxy-2-aceto-naphthone (HAN)在水中錯合------------------ 27
圖2-6. 環糊精與客分子的錯合模式 ------------------------------------------ 28
圖2-7. 對苯基酚 (4-phenylphenol),4, 4'-二羥基聯苯 (4, 4-biphenol)及酚 (phenol)與HP-?-CD錯合情形,分別以 (a) x-reciprocal, (b) y-reciprocal及(c) double-reciprocal 方程式作圖 ---------------------------------------------- 46
圖3-1. 毛細管電泳儀裝置圖 ------------------------------------------------ 51
圖4-1. 添加CM-?-CD於緩衝溶液中,烷基?環分子異構物電泳
遷移率的改變 -------------------------------------------------------------- 59
圖4-2. 添加3 mM CM-?-CD對烷基?環分子位置異構物分離效
果的影響之電泳圖,pH 6.0 -------------------------------------------------- 59
圖4-3. 添加CM-?-CD於緩衝溶液中,烷基?環分子異構物電泳
遷移率的改變,pH 8.8 ------------------------------------------------------ 62
圖4-4. 添加CM-?-CD於緩衝溶液中,烷基?環分子異構物電泳
遷移率的改變,pH 6.0 ------------------------------------------------------ 62
圖4-5 CM-?-CD與烷基?環分子錯合情形,分別以y-reciprocal方程式做圖 ------- 83
圖4-6 CM-?-CD與烷基?環分子錯合情形,分別以double-reciprocal方程式做圖 -- 85
圖4-7 CM-?-CD與烷基?環分子錯合情形,分別以x-reciprocal方程式做圖 ------- 87
圖 4-8 以van doff 方程式利用lnK與1/T做圖 --------------------------------- 94
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指導教授 丁望賢(Wang-Hsien Ding) 審核日期 2005-6-8
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