Development of a novel sugar linkage and sugar-related bioactive compounds

新型糖键和糖相关生物活性化合物的开发

• 批准号: 15590023
• 负责人: TAKAHASHI Hideyo
• 金额: $ 2.24万
• 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: 2003
• 资助国家: 日本
• 起止时间: 2003 至 2004
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-15590023/
• 关键词: Coyolosa; ether-linked sugar; ether bonding; reductive etherification; hypogelycemic activit; coyolosa

Coyolosa, a new natural product isolated from the Acrocomia mexicana root, has shown a significant effect on fasting blood glucose levels. While there can be no doubt that Coyolosa has a structure with two pyranoses linked at each of their 6-positions, it is less obvious that the stereochemistry of its pyranose moiety corresponds to the proposed structure. In this communication, we report a novel synthesis of 6, 6'-ether-connected pyranoses. Also, we reconsidered the stereochemistry of the proposed structure of Coyolosa based on the structure-activity relationships (SAR) studies. This is the first synthesis of ether-connected sugar based on an acetalization-reduction procedure.

土豆根是一种从墨西哥石竹根中分离出来的新天然产物，它对空腹血糖水平有显著的影响。虽然毫无疑问，Coyolosa有一个结构，在它们的6个位置上每个位置都连接了两个吡喃糖，但不太明显的是，它的吡喃糖部分的立体化学与所提出的结构相对应。在这篇通讯中，我们报道了一种新的6，6‘-乙醚连接的吡喃糖的合成。同时，基于构效关系(SAR)研究，我们重新考虑了拟合成的Coyolosa结构的立体化学。这是第一次基于缩醛-还原过程合成乙醚连接糖。

项目成果

Development of a novel sugar linkage:: 6,6′-ether-connected sugars

• DOI: 10.1002/anie.200352388
• 发表时间: 2003-01-01
• 期刊: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
• 影响因子: 16.6
• 作者: Takahashi, H;Fukuda, T;Ikegani, S
• 通讯作者: Ikegani, S

Synthesis of L-pyranosides from 5-enopyranosides by Diastereoselective hydroboration/oxidation

非对映选择性硼氢化/氧化从 5-烯吡喃糖苷合成 L-吡喃糖苷

• 发表时间: 2004
• 期刊: Synthesis (18)
• 作者: O.Hara;K.Sugimoto;K.Makino;Y.Hamada;Takahashi Hideyo;Hideyo Takahashi
• 通讯作者: Hideyo Takahashi

Synthesis of L-pyranosides from 5-enopyranosides

由5-烯吡喃糖苷合成L-吡喃糖苷

• 发表时间: 2004
• 期刊: Synthesis
• 作者: O.Hara;K.Sugimoto;K.Makino;Y.Hamada;Takahashi Hideyo
• 通讯作者: Takahashi Hideyo

Development of a novel suger linkage:6,6'-ether-connected sugars.

新型糖键的开发：6,6-醚连接糖。

• 发表时间: 2003
• 期刊: Angewandte Chemie, International Edition 42巻
• 作者: Takahashi;Hideyo
• 通讯作者: Hideyo

Takahashi, Hideyo: "Development of a novel sugar linkage : 6,6'-ether-connected sugars."Angewandte Chemie, International Edition. 42巻・41号. 5069-5071 (2003)

Takahashi, Hideyo：“新型糖键的开发：6,6-醚连接糖。”Angewandte Chemie，国际版，第 42 卷，第 41 期。5069-5071 (2003)