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研究生：	簡禎佑 Chien, Chen-Yu
論文名稱：	由深共熔溶劑促進酯肽交換反應:原生胜肽的簡易合成路徑 Ester-mediated peptide formation promoted by deep eutectic solvents: A facile pathway to proto-peptides
指導教授：	游聲盛 Yu, Sheng-Sheng
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：	2020
畢業學年度：	108
語文別：	英文
論文頁數：	111
中文關鍵詞：	深共熔溶劑、酯肽、原始胜肽、化學演化、生命起源、共聚多肽、胜肽序列控制
外文關鍵詞：	deep eutectic solvents, depsipeptides, proto-peptides, chemical evolution, origin-of-life, co-polypeptides, sequence control of peptides
相關次數：	點閱：164 下載：0
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傳統合成胜肽的方法有許多缺點，例如使用有害的溶劑以及缺乏有效的偶聯劑促進胺基酸形成胜肽鍵。在前人的研究中，藉由在乾溼循環反應中混合羥基酸和胺基酸，可不必透過添加偶聯劑而是透過形成酯肽來合成胜肽。然而此反應仍有諸多挑戰需要克服。首先，許多胺基酸或是多肽，在此種體系中的溶解度較低，形成不均質的系統造成反應效率降低。而在共聚合的過程中，易產生具有酯鍵以及醯胺鍵的隨機共聚酯肽，必須透過額外的水解反應才會產生胜肽，為了解決前述問題，在此研究中引入具有環境友善以及化學催化特性的深共熔溶劑來輔助胜肽的合成。
在此研究中，我們利用四級胺氯鹽形成深共熔溶劑以進行乙醇酸及甘胺酸的酯肽交換反應。乙醇酸可先與四級胺氯鹽以氫鍵作用形成深共熔溶劑，乙醇酸再與甘胺酸反應形成多肽。我們發現此種以羥基酸及四級胺氯鹽為主的深共熔溶劑可以有效地減少羧酸酯和胜肽鍵結形成的隨機共聚物，直接生成多肽。在我們測試的四級胺氯鹽中，四乙基氯化銨所形成的深共熔溶劑可促成最佳的單體轉化率並形成長鏈的胜肽。另外，在四乙基氯化銨的作用下，可選擇性地合成在N末端帶有乙醇酸的胜肽標準品，這些標準品可與四乙基氯化銨形成新的深共熔溶劑。傅立葉轉換紅外線光譜和示差掃描熱分析結果證實了深共熔溶劑中多肽與四乙基氯化銨形成氫鍵的交互作用以及極低的熱轉化溫度。四乙基氯化銨的濃度及乙醇酸/甘胺酸的比率會影響胜肽的產率和鏈長分佈。於深共熔溶劑中逐漸加入不同種類的胺基酸可以合成嵌段共聚多肽或是進行胜肽序列控制。推測在深共熔溶劑中可以合成高產量胜肽的可能機制如下: (一) 四級胺氯鹽與乙醇酸形成深共熔溶劑因而降低酯化速率; (二) 在四級胺氯鹽作用下，增強胺基酸中胺基的親核性以增進酯-醯胺交換反應形成胜肽鍵; (三) 在N末端帶有乙醇酸的胜肽產物進而與四級胺氯鹽形成穩定且均質的深共熔溶劑。
總結來說，深共熔溶劑不只擔任反應物以及反應溶劑的角色，亦是扮演催化劑的角色，選擇性的催化合成高產率的胜肽產物，因此，深共熔溶劑提供了一種無需使用偶聯劑和有毒溶劑且可以在溫和條件下簡單合成胜肽的方法。

Traditional ways to synthesize peptides have many drawbacks like using toxic solvents and coupling agents with low atomic efficiency. Previous reports proposed a pathway known as ester-mediated amide bond formation to synthesize peptides by mixing hydroxy acids and amino acids in an oscillating wet-dry cycle without using the coupling agents. However, the system yielded random copolymers linked by both amide and ester bonds under a heterogeneous environment. Additional hydrolysis treatment was required to reduce the complexity of products and to reveal the peptide backbones.
To address the above challenges, we introduce the concepts of deep eutectic solvents (DESs) into the synthesis of peptides because DESs are known for their sustainability and catalytic properties. Glycolic acid and tetraethylammonium chloride (TEACl) formed a DES as a solvent to dissolve amino acids. Glycolic acid then copolymerized with amino acids by esterification and ester-amide exchange reaction. We demonstrated DESs facilitated the formation of amino acids-enriched peptides rather than the depsipeptides with mixed esters and amides as backbones. Among all the quaternary ammonium chlorides tested, DESs containing TEACl showed the highest conversion of amino acids and enabled the formation of long chain peptides. Standard compounds of peptides with glycolic acid at the N-terminus could be selectively synthesized in the presence of TEACl. Additionally, we found the reaction mixtures and the mixtures of standard compounds with TEACl also formed DESs. The hydrogen bonding and the thermal transition temperature of DESs were confirmed by FT-IR and DSC. The yield and the distribution of peptides were also influenced by the concentration of TEACl and the ratio of glycolic acid/glycine. Peptides with desired sequences can also be achieved by gradually adding different amino acids into the DES system. The possible mechanism behind the selective synthesis of amino acids-enriched peptides with high yield in the DES may come from the following process: (1) Reduced rate of esterification by forming DES from TEACl and glycolic acid. (2) Enhanced nucleophilicity of amino groups to improve the rate of ester-amide exchange in the presence of TEACl. (3) Formation of stable and homogenous DES from the mixture of TEACl and products with glycolic acid residue at the N-terminus.
In summary, DES not only acts as the reaction medium and reactants, but also plays the role of catalyst to favor the formation of amino acids-enriched oligopeptides. Therefore, DES provides a facile and sustainable method to synthesize peptides under a mild condition without using coupling agents and toxic solvents.

摘要	                                                  I

Abstract                                                 II

Acknowledgements	                                 IV

List of tables	                                          i

List of figures	                                         ii

List of abbreviations	                                 ix

Chapter 1.	Introduction	                          1
1     Peptides	                                  1
1.1	Basic properties	                          1
1.2	Applications of peptides	                  4
1.3	Prebiotic chemistry about peptides	          7
2	Methods to synthesize peptides	                  9
2.1	Solid phase peptide synthesis (SPPS)	          9
2.2	Ring-opening polymerizations of α-amino acid N-carboxyanhydrides (ROP-NCAs)	                         12
2.3	Recombinant protein production	                 14
2.4	Prebiotic synthesis of peptides from ester-mediated amide bond formation driven by wet-dry cycle	         16
3	Deep eutectic solvents (DES)	                 18
3.1	Overview of deep eutectic solvents	         18
3.2	Applications of DES	                         20
4	Objectives	                                 23

Chapter 2.	Materials and methods	                 25
1	Materials	                                 25
2	Methods	                                         26
2.1	Synthetic procedures of standard compounds	 26
2.2	General procedures for the purification of standard compounds	                                         26
2.3	Identification of standard compounds	         27
2.4	Preparation of DESs from standard compounds and TEACl	                                                 27
2.5	Dry down reaction to synthesize peptide mixtures with different salts, hydroxy acids and amino acids	 27
2.6	Nuclear magnetic resonance (NMR) analysis	 28
2.7   High performance liquid chromatography coupled with UV detector (HPLC-UV) analysis	                         29
2.8	High performance liquid chromatography coupled with MS detector (HPLC-MS) and tandem MS analysis	         31
2.9	Fourier-transform infrared spectroscopy (FT-IR) analysis	                                         33
2.10	Differential scanning calorimetry (DSC) analysis 33

Chapter 3.	Identification and quantification of peptides in deep eutectic solvents	                 34
1	Introduction	                                 34
2	HPLC-MS and log2-ratio analysis of compound distribution with/without TEACl	                         35
3	Tandem MS analysis of 1gnG pure peptides and 1gnG1g depsipeptides	                                         40
4	The effect of different salts on the formation of deep eutectic solvents	                                 43
5	The effect of different salts on the product distribution	                                         45
6	Synthesis, purification and identification of standard compounds	                                 50
7	Conclusion	                                 61

Chapter 4.	The potential role of deep eutectic solvents on peptide synthesis	                         62
1	Introduction	                                 62
2	The effect of TEACl concentration on the distribution of 1gnG peptides	                         63
3	The effect of g/G ratio on the distribution of 1gnG peptides	                                         67
4	The effect of glycine concentration on the distribution of 1gnG peptides	                         70
5	FT-IR analysis of the deep eutectic solvents	 72
6	DSC analysis of the deep eutectic solvents	 81
7	The reaction of different hydroxy acids and amino acids in DESs	                                         83
8	Synthesis of the peptides with sequence control	 90
9	The effect of different salts on the homopolymerization of glycolic acid or glycine	         94
10	Possible mechanism to form amino acid enriched-peptides	                                         98
11	Conclusion	                                100

Chapter 5.	Conclusion	                        101

References	                                        102



                                    

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