簡易檢索 / 詳目顯示
| 研究生： |
鄭宇廷 Yu-Ting Cheng |
|---|---|
| 論文名稱： |
綠色醣鏈結反應：以Nafion® NR50樹脂促進硫醣苷之醣鏈結反應 Green Glycosylation: Promoting Thioglycoside by Reusable Nafion® NR50 Resin |
| 指導教授： |
王正中
Cheng-Chung Wang 謝發坤 Fa-Kuen Shieh |
| 口試委員: | |
| 學位類別： |
碩士 Master |
| 系所名稱： |
理學院 - 化學學系 Department of Chemistry |
| 論文出版年： | 2020 |
| 畢業學年度： | 108 |
| 語文別： | 中文 |
| 論文頁數： | 290 |
| 中文關鍵詞： | 醣鏈結反應 、硫醣苷 、樹脂 、可回收 |
| 外文關鍵詞： | glycosylation, thioglycoside, resin, reusable |
| 相關次數： | 點閱：12 下載：0 |
| 分享至: |
| 查詢本校圖書館目錄 查詢臺灣博碩士論文知識加值系統 勘誤回報 |
有機醣化學為有機化學中重要的分支，因為醣類在生物體中扮演著重要的角色，舉凡植物中的細胞壁，生物體內的細胞膜及血液中。由於某些重要醣體較難以從天然物中獲得，因此，有機化學合成的方式就顯得重要。近年來環保意識抬頭，綠色化學是近年科學家關注的課題之一，科學家希望能夠降低在化學反應中利用或產生對環境有害的物質。因此本論文的將以納菲樹脂（Nafion® NR50）取代醣基化反應中的酸來進行醣基化反應，且此納菲樹脂（Nafion® NR50）經過甲醇簡單清洗乾燥後可重覆利用達10次以上僅大約6%的產率下降，此舉已達到對環境友善的目的。本論文的後段將以有機合成方法製備一系列稀有葡萄糖胺雙醣結構，部分無法以納菲樹脂（Nafion® NR50）合成鏈結之醣體將以Koenigs–Knorr反應鏈結，目的為提供此一系列的雙醣與中央研究院原子與科學研究所合作建立雙醣資料庫，以利未來分析未知醣體時有質譜光譜資料可遵循。
Carbohydrates Chemistry is a large and important branch of organic chemistry, because carbohydrates play an important role in living organism, such as cell walls in plants, cell membranes and blood in organisms. Since some important sugars are difficult to obtain from natural sources, the method of organic chemical synthesis is important. In recent years, environmental awareness has risen. Green chemistry is one of the topics that scientists have paid attention to in recent years. Scientists hope to reduce the use or production of substances harmful to the environment in chemical reactions. Therefore, in this thesis, Nafion resin (Nafion® NR50) will be used to replace the acid in the glycosylation reaction, and this Nafion resin (Nafion® NR50) can be reused after simple washing and drying in methanol. Over 10 times, only about 6% of the yield has dropped, which has achieved the goal of being friendly to the environment. In the latter part of this thesis, a series of rare glucosamine disaccharide structures will be prepared by organic synthesis. Some sugars that cannot be synthesized with Nafion resin (Nafion® NR50) will be linked by Koenigs–Knorr reaction. The purpose is to provide this series of disaccharides cooperates with Institute of Atomic and Molecular Sciences, Academia Sinica to establish a disaccharide database to facilitate the future analysis of unknown sugars with mass spectrometry data.
[1] Fox, S. Human physiology, McGraw-Hill Education, 2015.
[2] Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
[3] Jefferis, R. Biotechnol. Prog. 2005, 21, 11-16.
[4] Holgersson, J.; Gustafsson, A.; Breimer, M. E. Immunol. Cell Biol. 2005, 83, 694-708.
[5] Brandley, B. K.; Schnaar, R. L. J. Leukocyte Biol. 1986, 40, 97-111.
[6] Zeng, X.; Andrade, C. A.; Oliveira, M. D.; Sun, X.-L. Anal. Bioanal. Chem. 2012, 402, 3161-3176.
[7] Wiederschain, G. Y. Essentials of glycobiology, Springer Science & Business Media, 2009.
[8] Walstra, P.; Walstra, P.; Wouters, J. T.; Geurts, T. J. Dairy science and technology, CRC press, 2005.
[9] Hattori, H.; Roesslein, J.; Caspers, P.; Zerbe, K.; Miyatake‐Ondozabal, H.; Ritz, D.; Rueedi, G.; Gademann, K. Angew. Chem., Int. Ed. 2018, 57, 11020-11024.
[10] Artsimovitch, I.; Seddon, J.; Sears, P. Clin. Infect. Dis. 2012, 55, 127-131.
[11] Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Kulkarni, S. S.; Huang, Y.-W.; Lee, C.-C.; Chang, K.-L.; Hung, S.-C. Nature 2007, 446, 896-899.
[12] Xu, L.; Qi, T.; Xu, L.; Lu, L.; Xiao, M. J. Carbohydr. Chem. 2016, 35, 1-23.
[13] Desmet, T.; Soetaert, W.; Bojarová, P.; Křen, V.; Dijkhuizen, L.; Eastwick‐Field, V.; Schiller, A. Chem. Eur. J. 2012, 18, 10786-10801.
[14] Seeberger, P. H.; Finney, N.; Rabuka, D.; Bertozzi, C. R. Chemical and enzymatic synthesis of glycans and glycoconjugates, Cold Spring Harbor Laboratory Press, 2009.
[15] Nilsson, K. G. Trends Biotechnol. 1988, 6, 256-264.
[16] Vidal, S. ACS Cent. Sci. 2020, 6, 83-86.
[17] Adero, P. O.; Amarasekara, H.; Wen, P.; Bohé, L.; Crich, D. Chem. Rev. 2018, 118, 8242-8284.
[18] Zhu, X.; Schmidt, R. R. Angew. Chem., Int. Ed. 2009, 48, 1900-1934.
[19] Lee, Y. C.; Lee, R. T. J. Chin. Chem. Soc. 1999, 46, 283-291.
[20] Demchenko, A. V. Handbook of chemical glycosylation: advances in stereoselectivity and therapeutic relevance, John Wiley & Sons, 2008.
[21] Wolfe, S.; Myung-Hwan, W.; Mitchell, D. J. Carbohydr. Res. 1979, 69, 1-26.
[22] Warrent, R. W.; Caughlan, C. N.; Hargis, J. H.; Yee, K.; Bentrude, W. G. J. Org. Chem. 1978, 43, 4266-4270.
[23] Mo, Y. Nat. Chem. 2010, 2, 666-671.
[24] Das, R.; Mukhopadhyay, B. ChemistryOpen 2016, 5, 401-433.
[25] Nigudkar, S. S.; Demchenko, A. V. Chem. Sci. 2015, 6, 2687-2704.
[26] Lu, S. R.; Lai, Y. H.; Chen, J. H.; Liu, C. Y.; Mong, K. K. T. Angew. Chem. Int. Ed. 2011, 50, 7315-7320.
[27] Satoh, H.; Hansen, H. S.; Manabe, S.; van Gunsteren, W. F.; Hünenberger, P. H. J. Chem. Theory Comput. 2010, 6, 1783-1797.
[28] Zhang, Z.; Ollmann, I. R.; Ye, X.-S.; Wischnat, R.; Baasov, T.; Wong, C.-H. J. Am. Chem. Soc. 1999, 121, 734-753.
[29] Chang, C. W.; Wu, C. H.; Lin, M. H.; Liao, P. H.; Chang, C. C.; Chuang, H. H.; Lin, S. C.; Lam, S.; Verma, V. P.; Hsu, C. P.; Wang, C.-C. Angew. Chem. Int. Ed. 2019, 58, 16775-16779.
[30] Bokor, E.; Kun, S.; Goyard, D.; Toth, M.; Praly, J.-P.; Vidal, S.; Somsak, L. Chem. Rev. 2017, 117, 1687-1764.
[31] Lee, Y. S.; Rho, E. S.; Min, Y. K.; Kim, B. T.; Kim, K. H. J. Carbohydr. Chem. 2001, 20, 503-506.
[32] Yang, G.; Wang, Q.; Luo, X.; Zhang, J.; Tang, J. Glycoconjugate J. 2012, 29, 453-456.
[33] Takeuchi, K.; Mukaiyama, T. Chem. Lett. 1998, 27, 555-556.
[34] Michael, A. J. Am. Chem. Soc. 1879, 1, 403.
[35] Tamura, J.-i.; Terayama, R.; Shimadate, T. J. Carbohydr. Chem. 1993, 12, 893-902.
[36] Koenigs, W.; Knorr, E. Ber. Dtsch. Chem. Ges. 1901, 34, 957-981.
[37] Fischer, E.; Armstrong, E. F. In Untersuchungen Über Kohlenhydrate und Fermente (1884–1908); Springer: 1909, 799-814.
[38] Hanessian, S.; Banoub, J. Preparation of 1, 2-trans-glycosides in the presence of silver trifluoromethanesulfonate, Elsevier, 1980.
[39] Helferich, B.; Zirner, J. Chem. Ber 1962, 95, 2604-2611.
[40] Meloncelli, P. J.; Martin, A. D.; Lowary, T. L. Carbohydr. Res. 2009, 344, 1110-1122.
[41] Helferich, B.; Gootz, R. Ber. Dtsch. Chem. Ges. 1929, 62, 2788-2792.
[42] Thiem, J.; Meyer, B. Chem. Ber. 1980, 113, 3075-3085.
[43] Lam, S. N.; Gervay-Hague, J. Org. Lett. 2002, 4, 2039-2042.
[44] Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763-764.
[45] Schmidt, R. R.; Michel, J. Angew. Chem. Int. Ed. 1980, 19, 731-732.
[46] Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21-123.
[47] Stick, R. V.; Williams, S. Carbohydrates: the essential molecules of life, Elsevier, 2010.
[48] Yu, B.; Tao, H. Tetrahedron Lett. 2001, 42, 2405-2407.
[49] Veeneman, G.; Van Leeuwen, S.; Van Boom, J. Tetrahedron Lett. 1990, 31, 1331-1334.
[50] Barroca, N.; Schmidt, R. R. Org. Lett. 2004, 6, 1551-1554.
[51] Tilve, M. J.; Gallo-Rodriguez, C. Carbohydr. Res. 2014, 397, 7-17.
[52] Huang, X.; Huang, L.; Wang, H.; Ye, X. S. Angew. Chem. Int. Ed. 2004, 43, 5221-5224.
[53] Verma, V. P.; Wang, C. C. Chem. Eur. J. 2013, 19, 846-851.
[54] Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Carbohydr. Chem. 1993, 12, 131-136.
[55] Urban, F. J.; Moore, B. S.; Breitenbach, R. Tetrahedron Lett. 1990, 31, 4421-4424.
[56] Schmidt, R. R.; Behrendt, M.; Toepfer, A. Synlett 1990, 1990, 694-696.
[57] Ogawa, H.; Koh, T.; Taya, K.; Chihara, T. J. Catal. 1994, 148, 493-500.
[58] Harmer, M. A.; Farneth, W. E.; Sun, Q. J. Am. Chem. Soc. 1996, 118, 7708-7715.
[59] Harmer, M. A.; Sun, Q. Appl. Catal., A 2001, 221, 45-62.
[60] Gorityala, B. K.; Ma, J.; Pasunooti, K. K.; Cai, S.; Liu, X.-W. Green Chem. 2011, 13, 573-577.
[61] Olah, G. A.; Mathew, T.; Farnia, M.; Prakash, G. S. Synlett 1999, 1999, 1067-1068.
[62] Li, M.; Bai, Y.; Zhou, J.; Huang, W.; Yan, J.; Tao, J.; Fan, Q.; Liu, Y.; Mei, D.; Yan, Q. MBio 2019, 10, 128-119.
[63] Courtneidge, J. L.; Lusztyk, J.; Pagé, D. Tetrahedron Lett. 1994, 35, 1003-1006.
[64] Green ChemistryLiu, C.; Shen, D.-M.; Chen, Q.-Y. Chem. Commun. 2006, 7, 770-772.
