研究生: |
陳維廷 Chen, Wei-Ting |
---|---|
論文名稱: |
6’-, 2-延伸之醣脂神經醯胺類似物製備之研究 Investigation on the preparation of 6’-, 2-derivatized galactosylceramide analogs |
指導教授: | 俞鐘山 |
口試委員: |
林武智
李德偉 |
學位類別: |
碩士 Master |
系所名稱: |
原子科學院 - 生醫工程與環境科學系 Department of Biomedical Engineering and Environmental Sciences |
論文出版年: | 2012 |
畢業學年度: | 100 |
語文別: | 中文 |
論文頁數: | 130 |
中文關鍵詞: | 自然殺手T細胞 、醣脂神經醯胺 、醣基化反應 、氫化 、醯胺化反應 |
外文關鍵詞: | iNKT Cells, galactosylceramide, glycosylation, hydrogenation, amide bond formation |
相關次數: | 點閱:2 下載:0 |
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本篇論文目的為製備可在6’-, 2-進行修飾之醣脂神經醯胺核心化合物(18) (6’-, 2-aminos galactosyl phytosphingosine)。論文中6’-, 2-胺基醣脂神經醯胺核心化合物之製備,醣端予體(6)是由商品化半乳醣經6步合成而得,產率為25%。受體(13)則由商品化神經鞘胺醇經由4步合成而得,產率為56%。再經由醣基化反應可得到醣脂質類似物,產率97%,而α/β比值為3。
核心化合(18) (6’-, 2-aminos galactosyl phytosphingosine)經由去甲醯基與氫化而得,總產率11.7%。
核心化合最後經由醯胺化最終分別得到醣脂神經醯胺類似物(19)、(20)、(21)、(22)。經由HPLC純化後,將分析其對於iNKT-Cell誘導增生之能力。
This thesis is aimed to prepare 6’-, 2-derivatized galactosylceramide analogs. Before preparation of core compound (18) 6’-, 2-aminos galactosyl phytosphingosine, donor (6) and acceptor (13) were firstly prepared. The sugar moiety (6) was obtained via a 6-step synthesis, starting from commercial galactose in 25% yield; the acceptor (13) was prepared from commercial phytosphingosine via 4-step synthesis in 41% yield. Then via glycosylation we obtained glycolsphingosine analog in 97% yield with α/β ratio of 3/1.
The core compound (18) was obtained via debenzoylation and hydrolysis and the total yield was 11.7%.
The final 6’-, 2-derivatized galactosylceramide analogs (19), (20), (21), (22), was obtained via amide bond formation and purified through HPLC. The analogs will be analyzed its potential as iNKT-Cell inducer.
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