以毛細管電泳法分離位置及對掌異構物之方法開法與應用

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蕭榮憶(Jung-Yi Hsiao) 查詢紙本館藏

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論文名稱

以毛細管電泳法分離位置及對掌異構物之方法開法與應用
(Application of caplillary electrophoresis to separate positional isomers and enantiomers)

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摘要(中)

異構物(isomers)係指擁有相同分子式之不同化合物，其中取代基排列位置不同者稱為位置異構物(positional isomer)，互為鏡像但不可重疊的立體異構物則為對掌異構物(enantiomer)。此二種異構物之間因分子量及帶電量相近或相同，無法利用毛細管區帶電泳法分離。本研究在緩衝溶液內添加對掌選擇劑(chiral selector)，使其與分析物錯合形成主客錯合物，產生視電泳遷移率之差異而達到分離之效果。
本研究的主要目標之ㄧ為利用毛細管電泳法分離?磺酸鹽位置異構物，並探討其與環糊精之間的作用關係，進而計算其結合常數與熱力學參數，以了解其分離機制。經由視電泳遷移率與對掌選擇劑(β-CD)濃度之關係，以非線性方程式及三種線性方程式所估算出之結合常數與文獻值比較，證實毛細管電泳法確為一便利且準確之結合常數計算方法。在資料數充分之條件下，四種估算結合常數之方程式中以非線性方程式所得之結果最為準確。實驗結果並顯示位置異構物取代基之種類、位置及數量會對錯合行為造成影響，當β位置上接有取代基時因立體障礙較小，結合常數較大，若取代基在α位置上則反之。此外，藉由不同溫度下結合常數之變化，可計算出主-客分子錯合作用時之熱力學參數變化。經由實驗結果得知?磺酸鹽與β-CD之錯合作用為自發性反應，且在溫度越低時趨勢越強。
本研究的第二目標即在建立一套方法，利用毛細管電泳法分離並檢測在水環境中的氯化苯氧基酸對掌異構物，並搭配前處理步驟以達到濃縮及去除基質干擾的目的。結果顯示，使用添加15 mM HP-β-CD的50 mM醋酸鹽緩衝溶液，施加25 kV的正向電壓所得到之分離效果最好。
一般毛細管電泳儀最常撘配UV偵檢器，其偵測極限都較高。因此，在真實水環境樣品的檢測上都須經過濃縮的步驟，以增加樣品的濃度。本研究所採用的萃取方法為固相萃取法，經由此方法可將樣品濃縮至少2000倍以上，並可去除部份基質干擾。但毛細管電泳法受離子的干擾影響很大，因此在進樣前必須增加一去鹽的步驟─鹽析，再次降低基質干擾。本研究所使用的鹽析條件為2 mL的水樣添加0.45 g NaOH，以1 mL的ACN進行萃取。經由搭配Oasis? HLB固相萃取管柱及鹽析的方法，當針對含有2.5 μg/L分析物之100 mL水樣進行回收率的探討，在最佳條件下各分析物之回收率均高於68%，相對標準偏差在13%以下，顯示本方法具有良好的回收率與再現性。

摘要(英)

Capillary electrophoresis (CE) is one of the most popular analytical techniques in separation of positional/structural isomers and chiral compounds, and also can be used to evaluate the binding constants and thermodynamic parameters of guest-host inclusion complex. The first part of this study is application of CE to simultaneously determine the apparent binding constants and thermodynamic parameters for six positional/structural naphthalene sulfonate derivatives with ?-cyclo- dextrin (?-CD). The change in electrophoretic mobilities were used to assess the binding constants by nonlinear regression and three different linear plots methods (named double reciprocal, x-reciprocal and y- reciprocal). The substituent group(s) attached to the naphthalene ring considerably affected the inclusion behaviors of these naphthalene sulfonate derivatives. The binding constant varies over almost one order of magnitude and a highly selective sequence is obtained between these guest model compounds. Naphthalenesulfonates with the substituent(s) at the 2-position(s) displayed stronger interaction with ?-CD, and gave well compatible results by these four plot methods. While at least one substituent was substituted into the 1-position of naphthalene showed the weak interaction or no interaction with ?-CD. Comparison to three linear regression methods, the non-linear regression method proves to be the most suitable for these determinations. Additionally, apparent binding constants for each structural isomer with ?-CD at several temperature, and thermodynamic parameters for binding were also calculated and discussed.
The second part of this study is application of CE to separate two groups of chiral chlorinated pesticides (dichloroprop and mecoprop) in water samples with (2-hydroxypropyl)-?-cyclodextrin (HP-?-CD). The most effective separation conditions were to use 50 mM ammonium acetate with 15 mM HP-?-CD at pH 4.6. Determination of the apparent binding constants and thermodynamic parameters for these two chiral pesticides were also calculated. The use of solid-phase extraction (SPE) and salting-out effect for the off-line preconcentration of chiral pesticides is demonstrated in this study. Oasis HLB-SPE cartridge was used to reduce interferences and enhance the extraction of analytes from surface water samples. The most effective salting-out effect was 0.45 g NaOH and 1.0 mL acetonitrile in 2-mL of SPE extract. Significantly sensitive improvement was observed and more than 2000-fold enrichment was achieved. Recovery of the analytes in various spiked water samples was up to 68% with RSD less than 13%.

關鍵字(中)

★ 熱力學參數
★ 位置異構物
★ 主-客錯合物
★ 結合常數
★ 環糊精
★ 毛細管電泳
★ 除草劑
★ 鹽析
★ 對掌異構物
★ 氯化苯氧基酸

關鍵字(英)

★ chlorophenoxy aicds
★ enantiomers
★ apparent binding constants
★ host-guest complex
★ naphthalenesulfonates
★ positional isomers
★ thermodynamic parameters
★ salting-out
★ herbicides
★ capillary electrophoresis
★ cyclodextrins

論文目次

中文摘要 --------------------------------------------------------------------- Ⅰ
英文摘要 --------------------------------------------------------------------- Ⅲ
目錄 --------------------------------------------------------------------------- Ⅴ
圖目錄 ------------------------------------------------------------------------ Ⅷ
表目錄 ------------------------------------------------------------------------ Ⅹ
第一章前言 --------------------------------------------------------------- 1
1-1 研究緣起 ------------------------------------------------------------- 1
1-2 研究目標 ------------------------------------------------------------- 4
第二章文獻回顧 --------------------------------------------------------- 8
2-1 毛細管電泳法 ------------------------------------------------------- 8
2-1-1 毛細管電泳法的歷史背景和發展 ----------------------- 8
2-1-2 荷電粒子的在電泳的遷移行為 -------------------------- 9
2-1-3 電滲透流與荷電粒子的遷移行為 ------------------------ 10
2-2 主客錯合現象 -------------------------------------------------------- 14
2-2-1 環糊精 --------------------------------------------------------- 14
2-2-2 內包錯合物 --------------------------------------------------- 19
2-2-3 ?磺酸鹽類 --------------------------------------------------- 23
2-3 對掌異構物的分離 -------------------------------------------------- 25
2-3-1 對掌異構物之簡介 ------------------------------------------ 25
2-3-2 對掌異構物分離研究之緣起 ------------------------------ 26
2-3-3 對掌異構物分離在環境檢測之重要性 ------------------ 27
2-3-4 毛細管電泳法於對掌異構物分離之應用 --------------- 28
2-4 氯化苯氧基酸 -------------------------------------------------------- 31
2-4-1 氯化苯氧基酸之簡介 --------------------------------------- 31
2-4-2 氯化苯氧基酸之性質 --------------------------------------- 31
2-4-3 氯化苯氧基酸之毒性 --------------------------------------- 35
2-4-4 氯化苯氧基酸之國內外相關研究 ------------------------ 35
2-5 鹽析 -------------------------------------------------------------------- 39
第三章實驗 ---------------------------------------------------------------- 42
3-1 實驗藥品與儀器設備 ----------------------------------------------- 42
3-1-1實驗藥品 ------------------------------------------------------- 42
3-1-2 儀器設備 ------------------------------------------------------ 45
3-2 實驗步驟 -------------------------------------------------------------- 46
3-2-1 標準品的製備 ------------------------------------------------ 46
3-2-2 緩衝溶液的製備 --------------------------------------------- 46
3-2-3 毛細管的處理 ------------------------------------------------ 47
3-2-4 毛細管電泳儀參數設定 ------------------------------------ 48
3-2-5 固相萃取步驟 ------------------------------------------------ 50
3-2-6 鹽析之步驟 --------------------------------------------------- 51
3-3 水樣採集 -------------------------------------------------------------- 51
第四章結果與討論 ------------------------------------------------------ 52
4-1 ?磺酸鹽位置異構物之分析 -------------------------------------- 52
4-1-1 毛細管環糊精修釋區帶電泳之分離 --------------------- 52
4-1-2 利用毛細管電泳法計算結合常數 ------------------------ 55
4-1-3 環糊精與?磺酸鹽錯合過程中熱力學參數之計算 --- 59
4-2 氯化苯氧酸對掌異構物之分析 ----------------------------------- 62
4-2-1 氯化苯氧基酸對掌異構物之波長選擇 ------------------ 62
4-2-2 氯化苯氧基酸對掌異構物之分離 ------------------------ 63
4-2-3 結合常數的計算 --------------------------------------------- 66
4-2-4 鹽析 ------------------------------------------------------------ 68
4-2-5 固相萃取法 --------------------------------------------------- 79
4-2-6 檢量線的製作 ------------------------------------------------ 80
4-2-7 真實樣品的檢測 --------------------------------------------- 81
第五章結論 --------------------------------------------------------------- 83
參考文獻 -------------------------------------------------------------------- 85
圖目錄
圖2-1 毛細管柱內壁表面矽醇基Si-OH解離示意圖 ---------------- 10
圖2-2 毛細管內壁之Stern電雙層模型 --------------------------------- 11
圖2-3 毛細管內之電位變化圖 ------------------------------------------- 12
圖2-4 電滲透流存在下的速度 ------------------------------------------- 13
圖2-5 環糊精結構通式 ---------------------------------------------------- 15
圖2-6 環糊精的種類 ------------------------------------------------------- 18
圖2-7 特定內包錯合物的錯合模式 ------------------------------------- 20
圖2-8 對掌異構物之特性 ------------------------------------------------- 25
圖2-9 氯化苯氧基酸的降解途徑 ---------------------------------------- 32
圖4-1 添加不同濃度的β-CD對?磺酸鹽位置異構物分離效果及遷移順序影響之電泳圖 -------------------------------------------------- 54
圖4-2 分別利用四種非線性及線性方程式繪圖所得之結果 ------- 58
圖4-3 以van’t Hoff方程式利用ln K與T-1做圖 ---------------------- 61
圖4-4 氯化苯氧基酸不同偵測波長之電泳圖 ------------------------- 62
圖4-5 在添加不同濃度的HP-β-CD於醋酸鹽溶液對氯化苯氧基酸對掌異構物分離效果及遷移順序影響之電泳圖 --------------- 64
圖4-6 添加不同濃度的HP-β-CD於甲酸鹽溶液對氯化苯氧基酸對掌異構物分離效果及遷移順序影響之電泳圖 ------------------ 65
圖4-7 混合溶液在玻璃管內分層的情形 ------------------------------- 68
圖4-8 不同樣品基質的電解質對於鹽析效應影響之電泳圖 ------- 69
圖4-9 添加不同的鹽類對於鹽析效應影響之電泳圖 ---------------- 71
圖4-10 有機溶劑種類對於以氫氧化鈉作為鹽類鹽析效應影響之電泳圖 --------------------------------------------------------------------- 73
圖4-11 有機溶劑種類對於以氯化鈉作為鹽類鹽析效應影響之電泳圖 -------------------------------------------------------------------------- 74
圖4-12 地下水水樣鹽析前後之電泳圖 ---------------------------------- 77
圖4-13 頭前溪水樣鹽析前後之電泳 ------------------------------------- 78
圖4-14 安平處理廠水樣鹽析前後之電泳圖 ---------------------------- 78
圖4-15 經不同前處理步驟的真實樣品之電泳圖 ---------------------- 82
表目錄
表1-1 ?磺酸鹽類之結構式，縮寫及其波峰之符號代號 --------- 6
表1-2 氯化苯氧基酸對掌異構物之結構式，縮寫及其波峰之符號代號 -------------------------------------------------------------------- 7
表2-1 國外針對氯化苯氧基酸分析方法之相關研究 ---------------- 38
表3-1 分離?磺酸鹽位置異構物之毛細管電泳儀設定參數 ------- 48
表3-2 氯化苯氧基酸對掌異構物之毛細管電泳儀設定參數 ------- 49
表4-1 在25度C下利用不同計算方程式所得之?磺酸鹽結合常數及經黏滯度校正後之結合常數並與文獻值比較 --------------- 57
表4-2 以毛細管電泳法搭配非線性曲線吻合法計算個別樣品與混合物與環糊精的結合常數 ------------------------------------------ 59
表4-3 ?磺酸鹽與β-CD在不同溫度下以非線性吻合法計算經黏滯度校正結合常數 --------------------------------------------------- 60
表4-4 β-CD與?磺酸鹽錯合之熱力學參數 --------------------------- 61
表4-5 氯化苯氧基酸與HP-β-CD間的錯合常數及錯合物遷移速率------------------------------------------------------------------------- 67
表4-6 ?磺酸鹽與HP-β-CD在不同溫度下以非線性吻合法計算經黏滯度校正結合常數 ------------------------------------------------ 67
表4-7 氯化苯氧基酸與HP-β-CD錯合之熱力學參數 --------------- 67
表4-8 鹽種類對鹽析效應的影響----------------------------------------- 72
表4-9 氫氧化鈉跟氯化鈉鹽析效果再現性比較 ---------------------- 72
表4-10 氫氧化鈉的量對鹽析效果的影響 ------------------------------- 75
表4-11 ACN體積對鹽析效應的影響 ---------------------------------- 76
表4-12 不同水樣的鹽析添加回收率 ------------------------------------- 77
表4-13 利用HLB固相萃取管柱的回收率 ------------------------------ 80
表4-14 檢量線線性關係與相對標準偏差值 ---------------------------- 81
表4-15 經固相萃取法-鹽析法之前處理步驟之真實樣品回收率 --- 82

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指導教授

丁望賢(Wang-Hsien Ding)

審核日期

2006-6-19

推文