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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 林俊宏(Chun-Hung Lin) | |
dc.contributor.author | Chia-Wei Hsu | en |
dc.contributor.author | 徐嘉偉 | zh_TW |
dc.date.accessioned | 2021-06-15T02:22:57Z | - |
dc.date.available | 2016-09-15 | |
dc.date.copyright | 2011-09-15 | |
dc.date.issued | 2011 | |
dc.date.submitted | 2011-08-17 | |
dc.identifier.citation | 1. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A., Glycobiology. Annu. Rev. Biochem. 1988, 57, 785-838.
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Wang, Z.; Zhou, L.; El-Boubbou, K.; Ye, X.-S.; Huang X., Multi-Component One-Pot Synthesis of the Tumor-Associated Carbohydrate Antigen Globo-H Based on Preactivation of Thioglycosyl Donors. J. Org. Chem. 2007, 72, 6409-6420. 35. Mong, T. K.-K.; Huang, C.-H.; Wong, C.-H., A New Reactivity-Based One-Pot Synthesis of N-Acetyllactosamine Oligomers. J. Org. Chem. 2003, 68, 2135-2142. 36. Love, K. R.; Seeberger, P. H., Solution Syntheses of Protected Type II Lewis Blood Group Oligosaccharides: Study for Automated Synthesis. J. Org. Chem. 2005, 70, 3168-3177. 37. Blatter, G.; Beau, J.-M.; Jacquinet, J.-C., The Use of 2-Deoxy-2-trichloro- acetamido-D-glucopyranose Derivatives in Syntheses of Oligosaccharides. Carbohydr. Res. 1994, 260, 189-202. 38. Blatter, G.; Jacquinet, J.-C., The Use of 2-Deoxy-2-trichloroacetamido -D-glucopyranose Derivatives in Syntheses of Hyaluronic Acid-Related Tetra-, hexanea-, and Octa-Saccharides Having a Methyl β-D-Glucopyranosiduronic Acid at the Reducing End. 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Res. 1985, 139, 105-113. 66. Fangour, S. E.; Guy, A.; Vidal, J.-P.; Rossi, J.-C.; Durand, T., Total synthesis of phytoprostane F1 and its 16 epimer. Tetrahedron Lett. 2003, 44, 2105-2108. 67. Speers, A. E.; Adam, G. C.; Cravatt, B. E.; Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3+2] cycloaddition. J. Am. Chem. Soc. 2003, 125, 4686-4687. 68. 謝効吾,合成硫酸化N-乙醯乳醣胺及其衍生物以用於半乳醣凝集素結合專一性之研究。國立台灣大學理學院化學系暨化學研究所碩士論文,中華民國98年6月。 69. 蔡秉霖,合成路易士X二聚體與KH-1醣抗原分子,國立台灣大學理學院化學所碩士論文,中華民國98年1月,第7頁。 | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/43531 | - |
dc.description.abstract | 本篇論文的主題以合成Galb-1,3-GlcNAc (type 1) 、Gal-b1,4-GlcNAc (type 2) 雙醣骨架為基礎,並在這些雙醣的3’、6’、6留下交錯保護基 (orthogonal protecting group) 以便進一步的後修飾,試圖完成三醣分子的合成方法。合成此類化合物將涉及有機醣化學合成中: (1) 醣予體(glycosyl acceptor) /醣受體 (glycosyl donor) 單元的設計與合成;(2) 醣苷鍵 (glycosidic bond) 的建立; (3) 如何選擇不會互相影響的醇類及胺類交錯保護基。
在合成方法的策略上,採取在還原端往後延伸,而在葡萄醣胺的胺上保護基對於醣苷鍵合成做了一系列的討論,而在醣苷鍵生成的位向選擇上則是利用僅調控溶劑系統與鄰近基效應 (neighbouring group participation effect) 來達成。 這些三醣分子構築體的設計可分為三個方向;從半乳醣的三號位置延伸alpha、beta兩種不同的異構物,其中Gal-a-1,3-Gal-b-1,3/1,4-GlcNAc是為人體紅血球上的ABO抗原上四種類型的其中兩種,是第一型與第二型 B antigen;Gal-b-1,3-Gal-b-1,3/1,4-GlcNAc 的b鍵結則是提供合成方法學的探討,最後在更換半乳醣構築體以得到GalNAc-b-1,4-Gal-b-1,4-GlcNAc的三醣分子,則可得到Sda/CT antigen 構築體。 | zh_TW |
dc.description.abstract | This thesis lays an emphasis on the three topics in carbohydrate chemistry including: (1) efficient synthesis of glycosyl acceptors/ glycosyl donors; (2) to construct glycosidic bonds with high yield and stetreoselectivity; (3) to develop orthogonal protecting groups for hydroxyl and amino groups.
We previously prepared a number of Galb-1,3/4-GlcNAc disaccharides with two features. First of all, a functionalized (an azide- or a carboxyester-containing) linker was attached to the reducing terminus of the saccharide products, as well as to be immobilized to the formerly developed carbohydrate array to measure the binding affinity with galectins. Additionally, we utilize orthogonally protecting groups to allow further modifications at specific positions of saccharides such as sulfation of hydroxyl group. In continuation of previous efforts, we aim at synthesizing Galb-1,3/4-GlcNAc-based trisaccharides in this thesis, i.e. the Gal or GalNAc residue will be introduced to the non-reducing end of Gal | en |
dc.description.provenance | Made available in DSpace on 2021-06-15T02:22:57Z (GMT). No. of bitstreams: 1 ntu-100-R98223126-1.pdf: 17048344 bytes, checksum: c716c92ba5f22c78b634c09a71f8a72c (MD5) Previous issue date: 2011 | en |
dc.description.tableofcontents | 誌謝 i
縮寫對照表 ii 中文摘要 iv ABSTRACT v 目錄 vi 圖目錄 viii 表目錄 x 流程目錄 xi Chapter 1 緒論 1 1.1 血型分類與醣體結構 1 1.2 化學醣苷鍵形成與離去基反應機構 4 1.3 一鍋化寡醣合成法 9 1.4 N-乙醯乳醣胺為核心之叁醣合成目標 17 Chapter 2 結果與討論 18 2.1 合成策略與逆合成分析 18 2.2 醣予體與醣受體的設計與合成 19 2.3 Galb-1,3/1,4GlcNAc 雙醣體合成討論 30 2.4 Galb-1,3/1,4GlcNAc-based 叁醣體合成與設計 31 2.5 叁醣一鍋化合成策略應用 34 2.6 結論 39 Chapter 3 Experimental Section 40 3.1 General Consideration. 40 3.2 Synthetic methods and physical data. 42 參考文獻 72 Appendix: 1H/13C NMR Spectra 82 | |
dc.language.iso | zh-TW | |
dc.title | 合成以N-乙醯乳醣胺為核心之三醣分子 | zh_TW |
dc.title | Synthesis of Galb-1,3/1,4-GlcNAc-based Trisaccharides | en |
dc.type | Thesis | |
dc.date.schoolyear | 99-2 | |
dc.description.degree | 碩士 | |
dc.contributor.oralexamcommittee | 蒙國光(Kwok-Kong Tony Mong),鄭偉杰(Wei-Chieh Cheng) | |
dc.subject.keyword | 醣化反應,交錯保護基,醣予體,醣受體, | zh_TW |
dc.subject.keyword | glycosylation,orthogonal protecting group,glycosyl donor,glycosyl acceptor, | en |
dc.relation.page | 120 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2011-08-17 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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