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Title: | 聚葡萄糖胺的程式編排一鍋化合成法 Programmable one-pot synthesis of poly glucosamine. |
Authors: | Chun-wei Chen 陳俊瑋 |
Advisor: | 翁啟惠(Chi-huey Wong) |
Keyword: | 一鍋化,葡萄糖胺,相對反應值, one-pot,glucosamine,RRV, |
Publication Year : | 2010 |
Degree: | 碩士 |
Abstract: | 自然界中,核酸和蛋白質的一級結構皆屬於直鏈狀聚合物。基於結構上的便利性,造就了自動化合成法的出現;至於醣類,卻因為結構的複雜性,尚無快速、有效的自動化合成法。程式編排一鍋化合成法,利用不同RRV值的醣予體,一個接著一個,可快速組裝成寡醣。因此,替醣類自動化合成帶來了一線曙光。
先前研究中指出,改變胺基的保護基亦會改變硫代醣苷(thioglycoside)的RRV值。本論文中,共使用了八種不同的氮端(N-)保護基,得到了八個不同大小的RRV值,也證實了不同的胺基保護基會影響醣予體(glycosyl donor)的反應活性。 藉由一鍋化合成的測試,發現氮端(N-)含有Boc保護基的醣予體,進行醣基化反應(glycosylation)時,會有遇酸水解情形產生。因此Boc系列的醣予體並不適用於醣基化反應。我們利用stepwise的方式將化合物14和化合物18的醣基化反應中,成功得到了雙糖化合物22。接下來再將化合物21與其反應得到三糖化合物23。最後,利用一鍋化合成法也成功得到化合物23。期望未來能夠藉由此策略,將其應用在聚葡萄醣胺(polyglucosamine)的合成。 Nucleic acids and proteins are the polymers of linear structure in nature. They can be synthesized via chemically automatic synthesis. However, saccharides are usually branched and very complex in structure. Till now, there is no automatic machine available for saccharides synthesis. To tackle this problem, a new synthesis strategy based on the different RRV of thioglucosides in a programmable one-pot approach has been developed. According to the previous studies, the RRV value is varied by changing amino protecting groups. There were eight different amino protecting groups of thioglycosides which had been synthesized in this thesis, and all of their RRV values were different in each other. Thereby, we confirmed that the RRV value is changed by different amino protecting group indeed. By the one-pot synthesis, there are some trouble in glycosylation about Boc group. It is not suitable donor for glycosylation as the Boc group will be removed in acid condition. However, trisaccharide could be synthesized by compound 14, compound 18 and compound 21. Therefore, V we want to get more polymers as many as possible in the future and it will be a new strategy for the synthesis of poly N-Acetylglucosamine. |
URI: | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/48707 |
Fulltext Rights: | 有償授權 |
Appears in Collections: | 化學系 |
Files in This Item:
File | Size | Format | |
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ntu-99-1.pdf Restricted Access | 14.2 MB | Adobe PDF |
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