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研究生： 呂龍岱
Lung-Dai Lu
論文名稱： 合成肝素與硫酸乙醯肝素雙醣分子庫
Synthesis of Heparin and Heparan Sulfate Disaccharide Library
指導教授： 洪上程
Shang-Cheng Hung
口試委員:
學位類別： 博士
Doctor
系所名稱： 理學院 - 化學系
Department of Chemistry
論文出版年： 2007
畢業學年度： 95
語文別： 英文
論文頁數： 286
中文關鍵詞： 硫酸乙醯肝素 、肝素 、葡胺巨醣
外文關鍵詞： heparan sulfate, heparin, glycosaminoglycan, GAG
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    • 硫酸乙醯肝素(heparan sulfate, HS)與肝素(heparin, HP)是屬於葡胺巨醣(glycosaminoglycan, GAG)的生物分子，硫酸乙醯肝素廣佈於細胞表面及胞外纖維組織裡，另一方面肝素則是只由巨細胞(mast cell)分泌而得的。硫酸乙醯肝素與肝素兩者均是具有負電荷性質的多醣體，主要的結構是由□1□4方式連接D式葡萄胺醣(GlcNH2)衍生物及□1□4方式連接D式葡萄醣酸(GlcA)或是L式艾杜醣酸(IdoA)。雖然兩者在結構上具有相似的特色，但是在生物系統中扮演的角色則是大大的不同，例如位於細胞表面上的硫酸乙醯肝素，在病毒感染、細胞成長及癌細胞轉移扮演非常重要的角色；而被巨細胞分泌的肝素多醣體則是在凝血現象中扮演不可或缺的角色。雖然兩者各自在不同的生化現象上具有重要的影響力，但是由於硫酸乙醯肝素在自然界中不容易取得，所以很多的生物學家都採用由牛肺與豬腸提煉而得的肝素，來作為研究硫酸乙醯肝素與其他生物分子(例如:病毒、細菌、或生物體重要的蛋白質)間作用的機制。但是對於醣類合成化學家來說，硫酸乙醯肝素與肝素畢竟還是屬於兩種不同的個體，各自有屬於自己的結構特色，並不適合混為一談。所以在這篇論文中，我們主要是想合成組成硫酸乙醯肝素與肝素多醣體中所可能包含的48種不同雙醣建構單元，並藉由這48個不同的建構單元，來合成一系列的硫酸乙醯肝素與肝素的雙醣分子庫。
    這篇論文大致上可分成八個章節，第一章主要是在描述細胞表面的醣類種類，並將重點著重在描述硫酸乙醯肝素與肝素兩者的結構與生物活性。第二章則是簡介目前幾位重量級醣類化學家對於合成硫酸乙醯肝素與肝素的工作。第三章則是我們自己實驗室對於合成硫酸乙醯肝素與肝素分子庫的目標與做法。
    第四章到第六章描述了我們對於構成硫酸乙醯肝素與肝素的單醣體建構單元的合成工作。在第四章中，我們經由7或8個步驟可以將D式葡萄胺醣轉換變成4種不同的醣予體。第五章則是關於另外兩種葡萄醣醣受體的合成，在這個部份，我們利用策略與作法是「醣類的位向選擇性一鍋化保護」。第六章描述了在自然界中稀少的L式艾杜醣的合成工作。
    第七章則是描述我們如何用手中現有的單醣體，來合成48個硫酸乙醯肝素與肝素分子庫，包含了16個具有疊氮、16個具有氮-乙醯基與16個具有氮-芐氧羰基官能基的雙醣體。最後我們在第八章則是利用兩個分別具有葡萄醣酸與艾杜醣酸的中間體來合成10個最終硫酸乙醯肝素與肝素雙醣體。
    第九章結論中，我們統整了第四到第八章的合成工作。第十章我們則是提供在合成過程中所需要的實驗步驟與新產生化合物的詳細物理資料。

    Heparan sulfate (HS) is a member of the glycosaminoglycan (GAG) family and close in structure to heparin (HP). HS and HP are structurally related linear polyanionic polysaccharides characterized by a repeating disaccharide unit of uronic acid [either □-L-iduronic (IdoUA) or □-D-glucuronic acid (GlcUA)] attached to a □-D-glucosamine (GlcNH2) unit. Although HP and HS have similar structural skeletons, their biological roles in vivo are quite different. There was a rapid growing interest in the structure and function of heparin sulfate whose heterogeneity enable these molecules to play important roles in various processes in the body. This dissertation is written to provide readers with a detailed review of the chemistry, structure, biological functions, and our contribution to this significant issue through synthesis of a full HP/HS disaccharide building block library.
    Chapter 1 describes cell surface environment and the definition of GAG family in the beginning. Furthermore, structural characterization of HP/HS molecules and their biological properties lead us to a deeper understanding of the relationship between heparin and heparan sulfate.
    Chapter 2 summarizes ten pioneers’ works in the literature reports and reveals the synthetic urgency of these molecules. Chapter 3 describes our concerns with HP/HS studies, our specific aims to solve the problems as well as the retro-synthetic plan.
    Chapters 4 to 6 illustrate our preparation of monosaccharide building blocks. Chapter 4 outlines the synthesis of four D-glucosamine glycosyl donors, in seven to eight steps, starting from D-glucosamine hydrochloride. Chapter 5 provides the synthetic schemes leading to two glucosyl acceptors. “A regioselective one-pot protection of carbohydrates” was developed and applied. Chapter 6 describes the process to afford two idopyranosyl acceptors, a rare unit in nature, via L-ido epoxide as a key intermediate.
    Chapter 7 outlines the synthesis of 48 disaccharide building blocks, including 16 azido-containing disaccharide, 16 N-acetylated disaccharides and 16 N-Cbz disaccharides. Finally, chapter 8 describes the preparation of a series of ten parent disaccharides through two common intermediates, linker-attached □-D-glucuronic and □-L-iduronic acid triol, to exemplify the feasibility of our strategies for our synthesis.
    Chapter 9 concludes our synthetic work described in chapters 4 to 8, and chapter 10 provides the experimental details of all of our synthesis work for this dissertation.

    Abstract...................................................i 摘 要....................................................iii 謝 誌......................................................v Abbreviations.............................................vi Content.................................................viii List of Figures............................................x List of Tables...........................................xii List of Schemes.........................................xiii List of Equations.........................................xv Chapter 1. Introduction....................................1 Structural characterization of HP/HS molecules............ 4 Biological properties of HP and HS....7 Chapter 2. Literature Reports for the Synthesis of HP and HS Oligosaccharides............................12 Sinaÿ’s method...........................................12 Petitou’s method.........................................13 Boons’s method...........................................14 Wei’s method.............................................15 Seeberger’s method.......................................16 Hung’s method............................................17 Martín-Lomas’s method....................................19 Wong’s method............................................20 Bonnaffé’s method........................................22 van der Marel’s method...................................25 Chapter 3. Specific Aims and Retrosynthetic Plans.........28 Specific aims.............................................28 Retro-synthetic plans.....................................29 Chapter 4. Synthesis of Four D-Glucosamine-Derived Glycosyl Donors.........................................32 Chapter 5. Synthesis of Two D-Glucopyranosyl Acceptors....36 Synthesis of the 2,3-O-dibenzyl thioglucopyranoside 121...38 Synthesis of the 2-O-benzoyl-3-O-benzyl thioglucopyranoside 126.......................................................39 Chapter 6. Synthesis of Two L-Idopyranosyl Acceptors......45 Synthesis of 1,6-anhydro-2-O-benzoyl-3-O-benzyl-□-L-idopyranose 37............................................45 Synthesis of 1,6-anhydro-2,3-di-O-benzyl-□-L-idopyranose 140.......................................................47 Chapter 7. Synthesis of 48 Disaccharide Building Blocks...49 Synthesis of 16 azido-containing disaccharide building blocks....................................................49 Synthesis of 16 N-acetyl-containing disaccharide building blocks....................................................59 Synthesis of 16 N-Cbz-containing disaccharide building blocks....................................................64 Chapter 8. Synthesis of Heparin and Heparan Sulfate Disaccharides..................................69 Synthesis of two common intermediates 199 and 206.........70 Our Synthesis of two final disaccharides 207 and 209......81 Our Synthesis of two final disaccharides 211 and 212......83 Our Synthesis of four final disaccharides 215, 218, 220 and 221.......................................................85 Our Synthesis of two final disaccharides 226 and 227......89 Chapter 9. Conclusion.....................................95 Chapter 10. Experimental Section..........................99 References...............................................189 Spectra..................................................198

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