細胞表面硫酸乙醯肝素寡醣的合成與內酯化反應探討

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研究生：	謝其榕 Chi-Rung Shie
論文名稱：	細胞表面硫酸乙醯肝素寡醣的合成與內酯化反應探討 Cell Surface Heparan Sulfate Oligosaccharides: Synthesis and Lactonization
指導教授：	洪上程
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：	2008
畢業學年度：	96
語文別：	英文
論文頁數：	296
中文關鍵詞：	硫酸乙醯肝素寡醣、肝素、葡胺聚醣、三氟甲磺酸金屬鹽、苯亞甲基縮醛還原開環反應、內酯化反應
外文關鍵詞：	Heparan Sulfate, Heparin, Glycosaminoglycan, Metal Trifluoromethanesulfonate, Regioselective Reductive Ring Opening of Arylidene Acetals, Lactonization
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Cell-surface heparan sulfate (HS) and its structurally related heparin (HP) play significant roles in a diverse set of biological processes, including cell-cell communication, viral infection, and molecular recognition. Because of the heterogeneous features of HS and HP, the structural information of HS/HP-protein complex remains unclear. Chemical synthesis is considered asone of the most practical way to obtain the pure and structurally verified oligosaccharides at a considerable scale. In this dissertation, we aim to prepare HS/HP oligosaccharides and resolve the difficulties encountered during the synthesis.
Chapter 1 describes the major components of the cell surface carbohydrates at the initial stage. The following structural characterization as well as biological properties of HP/HS is designed to provide a deeper understanding of the relationship between HP and HS. In Chapter 2 six known synthetic methodologies for preparing HP/HS oligosaccharides are summarized. The specific aims and the retro-synthetic plans to address new preparative routes are illustrated in Chapter 3. Chapter 4 outlines the preparation of the D-glucosamine-derived donor in seven steps, starting from D-glucosamine hydrochloride. The study of M(OTf)n-catalyzed regioselective reductive ring opening of arylidene acetals is discussed in Chapter 5. The isotope-labeled experiments are carried out to reveal the real mechanism of the ring opening reaction via a carbocation intermediate. Chapter 6 describes the construction of HP/HS oligosaccharide skeletons from reducing end to reducing end or from nonreducing end to reducing end. The latter approach is better than the former one, and an ultimate octasaccharide skeleton is reached.
The synthesis of HP/HS di-, tetra-, and hexasaccharides through an eight-step functional groups transformation of the corresponding sugar skeletons is illustrated in Chapter 7. Chapter 8 describes a new concept for HP/HS oligosaccharide lactonization.
The conclusion of our synthetic work is summarized in Chapter 9. A total synthesis of HP/HS di-, tetra-, and hexasaccharides is accomplished in a tactic and efficient way. In the process of this synthesis, a novel Cu(OTf)2-catalyzed regioselective ring opening is detailedly studied. Furthermore, interconversion between trisaccharide and its corresponding lactonized trisaccharide is identified. Finally, Chapter 10 provides the detailed experimental procedure and the characterization of all new compounds.

硫酸乙醯肝素(heparan sulfate, HS)與肝素(heparin, HP)是屬於葡胺聚醣(glycosaminoglycan, GAG)的生物分子。兩者皆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)。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。到目前為止已經被發現有許多生理反應或病毒的感染皆是透過和硫酸乙醯肝素的鍵結，然而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，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。因此，本論文將著重於如何使用化學合成來製備結構確定且成份均勻的硫酸乙醯肝素的寡醣體。
這篇論文大致上可分成十個章節，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寡醣的工作。第三章則是提出關於在這個領域中我們想要解決的幾個問題及我們想要合成的目標分子，並試著將目標分子進行反合成分析。
第四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，我們經由七個步驟可以將D式葡萄糖轉變成我們所需要的糖予體。第五章則有系統的探討各種三氟甲磺酸金屬鹽催化苯亞甲基縮醛還原開環反應的位向選擇性，並且在氘取代還原劑的作用下進行了一系列的氘取代標幟實驗，並試著提出合理的反應機構。
第六章描述了我們如何由還原端來建構寡醣體的骨架，在遇到了一些問題以後，我們將合成策略改由非還原端來建立寡醣體的骨架，八醣體是本篇論文中所合成最長的寡醣單元。第七章是描述將連結單元接上寡醣體骨架以後，經由八個步驟就可以得到硫酸乙醯肝素的雙醣體、四醣體以及六醣體。最後，第八章提出了關於硫酸乙醯肝素內酯化反應的概念，並用硫酸乙醯肝素三醣體為例，證明了三醣體及其內酯化產物可以互換的想法。
第九章結論中，我們統整了第四到第八章的合成工作。第十章則是提供了在合成工作中所需要的實驗步驟與新產生化合物的詳細物理性質與光譜資料。

Contents

Abstract...................................................i
摘 要....................................................iii
謝 誌......................................................v
Abbreviations...........................................viii
Content....................................................x
List of Figures.................................................xiii
List of Tables..................................................xvii
List of Schemes............................................... xviii
List of Equations................................................xxi
Chapter 1: General Introduction to Chemistry and Biology of Heparin and Heparan Sulfate....................................................1
1.1 Glycoconjugates on the cell surface environment............................................... 1
1.2 Structural characterization and biosynthesis of HP/HS molecules..................................................5
1.3 The Differences between heparin and heparan sulfate....6
1.4 Biological significance of heparin and heparan sulfate....................................................7
Chapter 2: Literature Review for the Synthesis of Heparin and Heparan Sulfate Oligosaccharides......................12
2.1 Sina□’s method.......................................12
2.2 Bonnaff□’s method....................................16
2.3 Hung’s method........................................19
2.4 Seeberger’s method...................................22
2.5 van der Marel’s method...............................29
2.6 Mart□n-Lomas’s method................................32
Chapter 3: Specific Aims and Retrosynthetic Plans.........37
3.1 Specific aims.........................................37
3.2 Retro-synthetic plans.................................38
Chapter 4: Synthesis of D-Glucosamine-derived Donor.......41
Chapter 5: Metal Trifluoromethanesulfonate-Catalyzed Regioselective Reductive Ring Opening of Arylidene Acetals...................................................47
    5.1 General introduction..............................47
    5.2 A thorough study for the optimal condition and its application to various arylidene acetals..................49
5.3 Isotope study.........................................62
5.4 Proposed Mechanism....................................64
Chapter 6: Synthesis of HP/HS Oligosaccharide Skeletons...68
6.1 Construction of the disaccharide moiety 154□ and its modification to our disaccharide glycosyl donor 152.......68
6.2 Elongation of HP/HS oligosaccharide skeletons from reducing end..............................................76
6.3 Elongation of HP/HS oligosaccharide skeletons from non-reducing end..............................................85
Chapter 7: Synthesis of HP/HS Di-, Tetra-, and Hexasaccharides...........................................89
7.1 Synthesis of the final HP/HS disaccharide 149.........89
7.2 Synthesis of the final HP/HS tetrasaccharide 150 and hexasaccharide 151........................................98
Chapter 8: Lactonization and Identification of Naturally Occurring HP/HS Trisaccharide............................103
8.1 General introduction of Helicobacter pylori (H. pylori for short)...............................................105
8.2 Synthesis of the parent HS trisaccharide as a model for the interconversion study................................110
Chapter 9: Conclusion....................................117
Chapter 10: Experimental Section.........................121
References...............................................208
Spectra..................................................222

                                

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