請用此 Handle URI 來引用此文件: http://hdl.handle.net/11455/14206
標題: (1)醣類六號位置之選擇性磷酸化反應 (2)以氯化物為媒介的葡萄醣胺立體選擇性醣鏈結反應之探討
(1)Regioselective C6 Phosphorylation of Carbohydrates (2)Chloride–mediated Stereoselective Glycosylation Reaction of Glucosamine Building Blocks
作者: 張峻瑋
Chang, Chun-Wei
關鍵字: 醣類
carbohydrates
碳水化合物
磷酸化
葡萄醣胺
醣鏈結
phosphorylation
glucosamine
glycosylation
出版社: 化學系所
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摘要: 碳 6 位置磷酸化的碳水化合物分子在代謝之初扮演重要的角色,最後會以肝醣的形式將能量儲存於體內。因此本論文的第一部份在於改良目前的實驗方法,開發一系列具備高位置選擇性之一鍋化的合成策略,將碳水化合物分子的碳 6 位置磷酸化並初步探討它們於生物體中行新陳代謝以及醣鏈結反應中的反應機構。 有效控制醣鏈結的立體位向是醣化學中相當具挑戰性的議題之一。不同於以往的文獻,我們發現醣鏈結反應中來自促進劑的氯離子會作為媒介參與醣鏈結反應,形成醣基氯化物進而影響立體選擇性。在本論文的第二部分中,我們致力於辨識中間產物─葡萄胺氯化物及探討其如何影響醣鏈結反應的立體選擇性。
In living organisms, the conversion of sugars to sugar 6-phosphates plays an important role in the initial stage of carbohydrate metabolisms, which result in the form of glycogen for the storage of energy. Therefore, in the first part of this thesis, a regioselective one-pot C6 phosphorylation of a series of sugar molecules has been developed and the roles of these sugar 6-phosphates in carbohydrate metabolisms are preliminarily investigated. Controlling the stereoselectivity in glycosylation reactions is one of the most challenging issues in carbohydrate chemistry. Different from commonly believed in the literature, we have found that the chloride from the promoters actually participates into the glycosylation reactions and affects the stereoselectivity. In the second part of this thesis, we focus on identifying the glycosyl chloride intermediates of glucosamine derivatives in the glycosylation reactions and how they influence the stereoselectivities.
URI: http://hdl.handle.net/11455/14206
其他識別: U0005-1107201323083900
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-1107201323083900
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