合成aminocyclitols(deoxyinosamines)及polyhydroxyindolizidines 的分子作為醣水解酵素抑制劑

淡江大學機構典藏 > 理學院 > 化學學系暨研究所 > 學位論文 > Item 987654321/32709

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题名:	合成aminocyclitols(deoxyinosamines)及polyhydroxyindolizidines 的分子作為醣水解酵素抑制劑
其它题名:	Synthesis of aminocyclitols(deoxyinosamines) and polyhydroxyindolizidines for potential glycosidase inhibitors
作者:	李恆毅;Li, Heng-yi
贡献者:	淡江大學化學學系碩士班施增廉;Shih, Tzenge-lien
关键词:	醣水解酵素抑制劑;Aminocyclitol;Indolizidine;Glycosidase inhibitor
日期:	2007
上传时间:	2010-01-11 02:36:41 (UTC+8)
摘要:	天然的polyhydroxylated aminosugars和其衍生物多為醣水解酵素抑制劑。已有文獻指出，抑制醣水解酵素(glycosidase)可治療癌症、病毒感染、糖尿病、內分泌失調等症狀，尤其是治療糖尿病的藥品，其商業價值相當驚人，預估在西元2010可從1.5億提升到2.2億的用藥人口，已是許多化學家及生化學家重點發展的目標。 Polyhydroxylated aminocyclitols和 indolizidines的衍生物，因其具備和醣類相似的結構，所以和醣水解酵素之間擁有奇特和有趣的作用，因此有潛力可以發展成為醣水解酵素抑制劑。我們以便宜且具對掌性質之D-(-)-quinic acid為起始物，成功的合成出不對稱的tetrahydroxy aminocyclitols。使用trans-4-hydroxy-L-proline作為起始物再搭配RCM(ring-closing metathesis)的合成策略成功的合成dihydroxylated indolizidines。我們希望合成出來的polyhydroxylated aminocyclitols和indolizidines的衍生物，能有好的生物活性。 Naturally occurring polyhydroxylated aminosugars are considered to be potential glycosidase inhibitors. These glycosidase inhibitors possess potential in the treatment of cancers, HIV, diabetes and metabolic disorders. Especially in diabetes, it is estimated that the number of diabetes patients is expectd to rise from the current estimated of 150 million to 220 million in 2010. Polyhydroxylated aminosugars have been known as glycosidase inhibitors. They display the same stereochemistry as the corresponding hexoses, exceptor nitrogen atom replacing the original oxygen. Herein we report a stereoselective synthesis of tetrahydroxylated aminocyclitols starting from D-(-)-quinic acid. Subsequent ring-closing metathesis (RCM) was employed to synthesize dihydroxylated indolizidines from trans-4-hydroxy-L-proline. The resulting tetra-hydroxylated aminocyclitols and di-hydroxylated indolizidines are glycosidase inhibitors.
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