Design and Synthesis of Highly Bioactive Sugar-Related Substances

高生物活性糖相关物质的设计与合成

• 批准号: 16590013
• 负责人: IKEGAMI Shiro
• 金额: $ 2.3万
• 依托单位: Teikyo University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2004
• 资助国家: 日本
• 起止时间: 2004 至 2005
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-16590013/
• 关键词: Coyolosa; Sugar lactone; L-Iduronic acid; 1-Methylglycoside; Selective glycosylation; Cyclitol; Antidiabetic drug; Voglibose; 新規エーテル糖構築法; ボグリボース

The following research results have been obtained in this research project.1) Coyolosa which is a natural disaccharide having an unusual structure with a 6,6'-ether- linkage was successfully synthesized. In connection with its anti-diabetic activity, 10 kinds of analogs have been synthesized and it was concluded that the reported structure should be revised. A 6,6'-disaccharide formed from two molecules of mannose might be proposed.2) In the connection of the conversion technique for D-sugar to the corresponding L-sugar with the ring opening and the recyclization, this methodology could be applied to the effective formation of L-aza-sugars and L-thia-sugars.3) Glycosylation using 1-methylenesugar afforded the corresponding α-D-glycoside stereo-selectively. This method could be also applied to synthesize the various types of α-glycosides such as α-oligosaccharides exhibiting a potent biological activity. The penta-saccharide analogue for PI-88 that will be expected as a heparanase inhibitor could be synthesized in a fully protected form.

本课题主要取得了以下研究成果：1）成功合成了一种天然双糖Coyolosa，它具有独特的6，6 ′-醚键结构。结合其抗糖尿病活性，合成了10种类似物，并对文献报道的结构进行了修正。2）将D-糖开环转化为相应的L-糖的方法与1-亚甲基糖的糖基化反应相结合，可有效地合成L-氮杂糖和L-硫杂糖; 3）立体选择性地合成相应的α-D-糖苷。该方法也可用于合成各种具有生物活性的α-糖苷类化合物，如α-寡糖。预期作为乙酰肝素酶抑制剂的PI-88的五糖类似物可以以完全保护的形式合成。

项目成果

Assembled catalyst of palladium and non-cross-linked amphiphilic polymer ligand for the efficient heterogeneous Heck reaction

钯和非交联两亲聚合物配体组装催化剂用于高效非均相 Heck 反应

• 发表时间: 2004
• 期刊: Tetrahedron 60
• 作者: Y.M.A.Yamada;K.Takeda;H.Takahashi;S.Ikegami
• 通讯作者: S.Ikegami

Synthesis of Cyclophellitol utilizing Palladium Chloride Mediated-Ferrier-II Rearrangement

利用氯化钯介导的 Ferrier-II 重排合成环己醇

• 发表时间: 2005
• 期刊: Molecules 10
• 作者: S.Takahashi;N.Ogawa;N.Sakairi;T.Nakata;Hideyo Takahashi;Hideyo Takahashi
• 通讯作者: Hideyo Takahashi

Determination of the Optical Purity of N-Nitrosofenfluramine found in the Chinese Slimming Diet

减肥药中N-亚硝基芬氟拉明光学纯度的测定

• 发表时间: 2003
• 期刊: Yakugaku Zasshi (Japanese) 123(9)
• 作者: A.Nakadai;H.Inagaki;M.Minami;H.Takahashi;R.Namme;M.Ohsawa;S.Ikegami^*
• 通讯作者: S.Ikegami^*

Synthesis of N-Protected Azaoligosaccharides and Their Cyclic Derivatives

N-保护的偶氮低聚糖及其环状衍生物的合成

• 发表时间: 2005
• 期刊: Tetrahedron Letters 46(No.14)
• 作者: S.Takahashi;N.Ogawa;N.Sakairi;T.Nakata;Hideyo Takahashi;Hideyo Takahashi;Daisuke Sawada
• 通讯作者: Daisuke Sawada

Short-Step Synthesis of 5-Thio-L-hexopyranoses from D-Gluconothio-O-lactone

由 D-硫代葡萄糖-O-内酯短步合成 5-硫代-L-吡喃己糖

• 发表时间: 2005
• 期刊: Heterocycles 66
• 作者: S.Takahashi;N.Ogawa;N.Sakairi;T.Nakata;Hideyo Takahashi;Hideyo Takahashi;Daisuke Sawada;Rie Namme;Hiromi Hamamoto;Daisuke Sawada
• 通讯作者: Daisuke Sawada