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研究生： 薛任杰
Jen-Chieh Hsueh
論文名稱： 酶催化反應對甘氨酸多晶型的影響
The Influence of Enzymatic Reaction on Glycine Polymorphism
指導教授： 李度
Tu Lee
口試委員:
學位類別： 碩士
Master
系所名稱： 工學院 - 化學工程與材料工程學系
Department of Chemical & Materials Engineering
論文出版年： 2021
畢業學年度： 109
語文別： 英文
論文頁數： 145
中文關鍵詞： 酶催化反應 、甘胺酸 、多晶型
外文關鍵詞： Enzymatic reaction, Glycine, Polymorphism
相關次數： 點閱：14  下載：0 
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    • 綠色化學是當今世界 的重要議題。 透過 催化 反應可 反應可 反應可 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 提高反應速率符合綠色化學的 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 範疇。在這項研究中，我們成功地優化了酶水解反應過程並確認酰基轉移的可 重複使用性。我們酰基轉移酶作為生物催化劑，在 重複使用性。我們酰基轉移酶作為生物催化劑，在 重複使用性。我們酰基轉移酶作為生物催化劑，在 重複使用性。我們酰基轉移酶作為生物催化劑，在 重複使用性。我們酰基轉移酶作為生物催化劑，在 35°-40°C、pH=7 的水中解 的水中解 的水中解 的水中解 的水中解 N-乙酰甘氨酸 以形成乙酰甘氨酸 以形成乙酰甘氨酸 以形成。甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 甘氨酸有幾種趣的多晶型物 ：α-、β-和 γ-甘氨酸 。甘氨 酸的多晶型物通常過在水中 酸的多晶型物通常過在水中 酸的多晶型物通常過在水中 再結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多結晶 製備。為了探究酶的添加是否影響甘氨酸多型，我們 型，我們 型，我們 型，我們 藉著 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 四個過程製備了甘氨酸晶體：（ 1）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， ）通過添加抗溶劑從水中再結晶甘氨酸， （2）通過抗溶劑對 ）通過抗溶劑對 ）通過抗溶劑對 ）通過抗溶劑對 ）通過抗溶劑對 ）通過抗溶劑對 ）通過抗溶劑對 N-乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 乙酰甘氨酸使用基轉移酶在 35°-40°C下攪拌一天水解 反應 產生的甘氨酸進行抗溶劑結晶。 產生的甘氨酸進行抗溶劑結晶。 產生的甘氨酸進行抗溶劑結晶。 產生的甘氨酸進行抗溶劑結晶。 (3) 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 在酰基轉移酶存下通過添加抗溶劑從水中再結 晶甘氨酸，以及 晶甘氨酸，以及 晶甘氨酸，以及 晶甘氨酸，以及 晶甘氨酸，以及 晶甘氨酸，以及 晶甘氨酸，以及 (4) 在 酰基轉移酶存在 酰基轉移酶存在 酰基轉移酶存在 酰基轉移酶存在 酰基轉移酶存在 酰基轉移酶存在 酰基轉移酶存在 酰基轉移酶存35°-40°C下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 下攪拌一天並通過添加抗溶劑從水 中再結晶甘氨酸。 比較了四種方法在 比較了四種方法在 比較了四種方法在 比較了四種方法在 比較了四種方法在 比較了四種方法在 比較了四種方法在 比較了四種方法在 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 添加抗溶劑結晶前調整 pH值至 4, 7 與 10的結 果。 N-乙酰甘氨酸在 乙酰甘氨酸在 乙酰甘氨酸在 乙酰甘氨酸在 乙酰甘氨酸在 乙酰甘氨酸在 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 酸性、鹼和中環境下經酰基轉移酶水解得到的甘氨晶體均 為高純度 β-甘氨酸 。然而 ，其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 其他三種方法幾乎都 產出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合出了不同多晶型物 的混合。

    Green chemistry (sustainable chemistry) is an important issue in the whole world now. The use of catalysts to increase the reaction rate is in line with the scope of green chemistry. In this work, an enzymatic hydrolysis reaction process has been successfully intensified and the hydrolytic enzyme acylase can be recycled and reused. Acylase was used as a biocatalyst to hydrolyze N-acetylglycine to form glycine in water at pH=7 at 35° to 40°C . The hydrolyzed glycine has three interesting polymorphs: α-, β- and γ-glycine. Polymorphs of glycine are usually made by recrystallization in water. To explore further of whether the addition of enzymes affects the polymorphism of glycine, we prepared glycine crystals through the four approaches: (1) recrystallization of glycine from water by antisolvent addition, (2) antisolvent crystallization of glycine produced by the hydrolysis of N-acetylglycine via acylase, stirred at 35° to 40°C for a day, (3) recrystallization of glycine from water by antisolvent addition in the presence of acylase, and (4) recrystallization of glycine from water by antisolvent addition in the presence of acylase, stirred at 35° to 40°C for a day. The pH values were adjusted to 4, 7 and 10 for all abovementioned methods before antisolvent addition for crystallization. The results of the above four methods were then compared. The glycine crystals obtained by the hydrolysis of N-acetylglycine via acylase under acidic, alkaline and neutral environments were all high-purity β-glycine. However, the other three methods almost gave a mixture of various glycine polymorphs.

    Table of Contents 摘要 ................................ ................................ ................................ ................................ i Abstract ................................ ................................ ................................ ......................... ii Table of Contents ................................ ................................ ................................ ......... iv List of Figures ................................ ................................ ................................ ............. vii List of Tables ................................ ................................ ................................ .............. xiv List of Schemes ................................ ................................ ................................ .......... xvi Chapter 1 Introduction ................................ ................................ ............................... 1 Green Chemistry ................................ ................................ ........................ 1 Biocatalytic Process ................................ ................................ ................... 4 Introduction of Glycine ................................ ................................ .............. 9 Glycine Polymorphism ................................ ................................ ............. 11 Method of Controlling Polymorphs of Glycine ................................ ........ 20 Conceptual Framework ................................ ................................ ............ 23 Chapter 2 Experimental Section ................................ ................................ ............... 25 Materials ................................ ................................ ................................ .. 25 2.1.1 Chemicals................................ ................................ .......................... 25 2.1.2 Solvents ................................ ................................ ............................. 25 v Experimental Methods ................................ ................................ ............. 28 2.2.1 Initial Solvent Selection of Glycine ................................ .................. 28 2.2.2 Solubility Measurement ................................ ................................ .... 29 2.2.3 Glycine Recrystallization by Cooling in Water ................................ . 30 2.2.4 Glycine Recrystallization by Antisolvent Addition ........................... 30 2.2.5 Original Process for Glycine Production by Enzymatic Reaction ..... 31 2.2.6 Intensified Process for Glycine Production by Enzymatic Reaction . 33 2.2.7 Glycine Recrystallization by Antisolvent Addition at Different pH Values ................................ ................................ ................................ 35 2.2.8 Recycling and Reuse of Acylase ................................ ....................... 40 Analytical Instruments ................................ ................................ ............. 41 2.3.1 pH-indicator Strips ................................ ................................ ............ 41 2.3.2 Optical Microscopy (OM) ................................ ................................ . 41 2.3.3 Fourier Transform Infrared (FTIR) Spectroscopy ............................. 42 2.3.4 Powder X-ray Diffraction (PXRD) ................................ ................... 42 2.3.5 Ultraviolet and Visible (UV/Vis) Spectrophotometer ........................ 43 2.3.6 Centrifugation ................................ ................................ ................... 44 2.3.7 Fluorescence Spectrophotometer ................................ ...................... 45 Chapter 3 Results and Discussion ................................ ................................ ............ 47 vi Use Test of Glycine ................................ ................................ .................. 47 3.1.1 FT-IR Spectroscopy ................................ ................................ .......... 47 3.1.2 PXRD Diffractometer ................................ ................................ ....... 49 Initial Solvent Screening ................................ ................................ .......... 51 3.2.1 Solubility Curve ................................ ................................ ................ 53 3.2.2 Glycine Recrystallization by Cooling in Water ................................ . 54 3.2.3 Glycine Recrystallization by Antisolvent Addition ........................... 55 Process Intensification of Enzymatic Reaction for Glycine ..................... 58 Recycling and Reuse of Acylase ................................ .............................. 63 Factors Affecting Glycine Polymorphism: pH, Solvent and Enzymatic Reaction ................................ ................................ ................................ ... 75 3.5.1 Influence of Solvent and pH on the Glycine Polymorphism ............. 76 3.5.2 Influence of Solvent, pH and Acylase on Glycine Polymorphism .... 82 Acylase Conformations ................................ ................................ ............ 97 Chapter 4 Conclusions and Future Works ................................ .............................. 106 Conclusions ................................ ................................ ............................ 106 Future Works ................................ ................................ .......................... 107 References ................................ ................................ ................................ ................. 109

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