請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/90607
標題: (1) Concise Synthesis of Ganglioside Hp-s1 analogues Varying at Glucosyl Moiety (2) Development of Highly alpha-selective O-Sialylation with Various p-Tolyl Thiosialoside Based on Pre-activation Method
(1) 葡萄醣上修飾化神經節苷脂Hp-s1衍生物之簡潔合成 (2) 利用預活化方法發展高alpha-位向選擇性唾液酸醣苷化反應
作者: 楊世安
Shih-An Yang
關鍵字: Ganglioside Hp-s1 analogues
neuritogenic activity
O-sialylation
醣苷神經鞘胺脂質
神經再生活性
神經節苷脂Hp-s1
唾液酸醣苷化反應
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摘要: Ganglioside Hp-s1 1 a well known ganglioside which was identified from the ovary of sea urchin Diadema setosum displays good neuritogenic activity. Therefore, in the first part of this thesis, we have designed and synthesized new analogues (2a-2e) of ganglioside Hp-s1 by changing the stereochemistry of central glucosyl moiety with alpha-glucopyranoside, beta and alpha-galactopyranoside, and alpha-mannopyranoside. This thesis focuses on the synthesis of 2a and 2e, after hopes of a better neuritogenic activity. Controlling the stereoselectivity in sialylation is one of the challenging in sialic acid. Therefore, in the second part of this thesis, we development novel method for pre-activation of p-tolyl thiosialoside donor with AgOTf and p-toluenesulfenyl chloride followed by sialylation with p-tolyl thioglycosides acceptor. Expect excellent alpha-sialylation yields. Herein, we focus on use the different p-tolyl thiosialoside donor in the sialylation and how they influence the stereoselectivities.
醣苷神經鞘胺脂質Hp-s1 1,可由刺冠海膽的卵巢中所分離得到,並且具有良好的神經再生活性。所以,本論文的第一部份,我們將Hp-s1 1中間的葡萄醣,置換成alpha-D-葡萄醣(glucose)、alpha-D-半乳醣(galactose)、beta-D-半乳醣以及alpha-D-甘露醣(mannose),用本實驗室所發表的方法合成出新的衍生物2a-2e,而本論文主要著重在2a及2e之合成,之後期許有更好之神經再生活性。 控制唾液酸醣鏈結反應之立體位向,是目前非常熱門且具有挑戰性的課題之一。因此本論文的第二部份中,我們想發展一種新穎的方法,利用AgOTf及p-TolSCl,將唾液酸醣予體進行預活化,之後與硫代醣受體進行醣鏈結反應,以期望有好的alpha-位向選擇性。在此,我們著重在使用不同的唾液酸醣予體,以探討醣鏈結反應之立體選擇性。
URI: http://hdl.handle.net/11455/90607
文章公開時間: 2018-06-12
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