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研究生:迦納辛
研究生(外文):Ganesh Shelke
論文名稱:第一章.基於預活化的溫和且高-選擇性的O-唾液酸化法: 獲取神經節苷脂 Hp-s1, DSG-A及它們的衍生物.第二章.β(1→4)鏈結的三醣及四醣葡萄糖胺醣胜肽的反覆合成.
論文名稱(外文):Chapter 1.Mild and Highly α-Selective O-Sialylation Method Based on Pre-activation: Access toGangliosides Hp-s1, DSG-A, and their Analogues.Chapter 2.Iterative Synthesis of β(1→4) linked tri- and tetra- Glucosamine glycopeptide.
指導教授:羅順原
口試委員:侯明宏梁健夫王正中鄭偉杰
口試日期:2017-09-25
學位類別:博士
校院名稱:國立中興大學
系所名稱:化學系所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2017
畢業學年度:106
語文別:英文
論文頁數:405
中文關鍵詞:唾液酸化法葡萄糖胺醣胜肽神經節苷脂
外文關鍵詞:gangliosidesHp-S1DSG-Aglycoproteins
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Chapter 1.
Mild and Highly α-Selective O-Sialylation Method Based on Pre-activation: Access to
Gangliosides Hp-s1, DSG-A, and their Analogues.
In Chapter 1, we described the imortance of Gangliosides Hp-s1, DSG-A and by using
various methods, these molecules are synthesized. For the stereoselective installation of alpha sialosides to glycosyl acceptors, we developed the mild and effective method. The method has selectivity for promary acceptors over secondary. The ceramide was assembled by using commercially available raw materials which is shortest till date reported. In part II, we
designed the molecules with modified ceramide part and synthesized them according to literature reports. Finally after having all compunds in hand, we tested them for neurotological activites which will help for further structure activity relationship study.
Chapter 2.
Iterative Synthesis of β(1→4) linked tri- and tetra- Glucosamine glycopeptide. This chapter describes the glycopeptides and its potential applications for chemotherapy
and imaging probe for tumor angiogenesis. We successively developed the chemical method to synthesis of di-, tri-, and tetra-saccharide glucosamine and coupled them with lipid chains. The deprotection and purification was tackled according to various techniques.The chain length of sugars can be increase by using the same method. We hope a significant
achievement to develop a new drug which can be a selective to tumor cells.
TABLE OF CONTENTS
ACKNOWLEDGEMENTS ..................................... i
ABSTRACT ...............................................iii
Chapter1. ................................................................................................. - 1 -
1.1. Objective of Study .......................................................................... - 1 -
1.2. Introduction ..................................................................................... - 2 -
1.2.1. Why sialic acids are important .................................................................................. - 2 -
1.2.2. Gangliosides ................................................................................................................. - 5 -
1.2.3. Synthetic approach to gangliosides and their analogs ............................................. - 8 -
1.2.4. Literature Synthetic Review....................................................................................... - 9 -
1.3. Part I. Synthesis of ganglioside Hp-s1 1, DSG-A 2 by using preactivation
strategy. ................................................................................... - 18 -
1.3.1. Fine tuning of pre-activation method. ..................................................................... - 18 -
1.3.2. Synthesis of ceramide derivatives ............................................................................ - 28 -
1.3.3. Final assembling of gangliosides .............................................................................. - 30 -
1.4. Part II. Synthesis of ganglioside analogs by other methods. ........ - 33 -
1.4.1. Replacement of anomeric oxygen by sulfer ............................................................ - 34 -
1.4.2. Deprotection strategy ................................................................................................ - 37 -
1.5. Biology .......................................................................................... - 41 -
1.6. Conclusions ................................................................................... - 44 -
Chapter 2. ............................................................................................... - 46 -
2. Iterative Synthesis of β(1→4) linked tri- and tetra- Glucosamine
glycopeptide. ............................................................................................ - 46 -
2.1. Introduction ................................................................................... - 46 -
2.1.1. Peptides ...................................................................................... - 46 -
vi
2.1.2. Glycans ....................................................................................... - 46 -
2.2. Nature and distribution of Glycopeptide linkages of Glycopproteins . -
47 -
2.2.1. The Important units of Glycopeptides. ...................................... - 48 -
N-glycosidic bonds .................................................................................................................. - 48 -
O-glycosidic bonds .................................................................................................................. - 49 -
C-mannosyl bonds ................................................................................................................... - 49 -
Phosphoglycosyl bonds ........................................................................................................... - 49 -
2.2.2. Chitin .......................................................................................... - 49 -
2.2.3. Chitosan ..................................................................................... - 50 -
2.2.4. Chemical Synthesis of Glycopeptides ....................................... - 56 -
2.2.5. Synthesis of Acceptor ................................................................ - 57 -
2.2.6. Synthesis of Donor ..................................................................... - 59 -
2.2.7. Synthesis of target 1a ................................................................. - 63 -
2.2.8. Synthesis of target 1b ................................................................. -64 -
2.2.9. Synthesis of target 1c ................................................................. - 66 -
2.2.10. Conclusions ............................................................................. -68 -
References ............................................................................................... - 69 -
Chapter 3. Experimental Section ......................................................... - 76 -
3. ............................................................................................................... - 76 -
3.1. General Information ...................................................................... - 76 -
3.2. Part I .............................................................................................. - 77 -
3.3. Part II ........................................................................................... - 114 -
vii
3.4. Iterative Synthesis of β(1→4) linked tri- and tetra- Glucosamine
glycopeptide Exp. Section...........................................................................157
3.5. NMR spectras of chapter 1………………………………………........172
3.6. NMR spectra of chapter 2……………………………………….........375
4.0. Publications…………………………………………………………...409
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