Development of Synthetic Host Molecule Aiming to Artificial Enzymes for Sugar Synthesis

针对糖合成人工酶的合成宿主分子的开发

• 批准号: 23655124
• 负责人: ABE Hajime
• 金额: $ 2.33万
• 依托单位: University of Toyama
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Challenging Exploratory Research
• 财政年份: 2011
• 资助国家: 日本
• 起止时间: 2011 至 2013
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-23655124/
• 关键词: エチニルピリジン; 大環状化合物; ピリジン; フェノール; 糖; ホスト・ゲスト化学; 薗頭反応; カプセル型分子; ホルモース反応; グリコシル化反応; 大環状分子; 人工酵素

Pyridine-phenol alternating macrocyclic oligomers, which were designed for strong saccharide recognition ability, have been developed in this research. The qualitative study on 1H NMR and DFT calculation studies suggested that the saccharide recognition ability is much stronger than we expected before the project. However, the self-aggregation of the host was a serious problem for saccharide recognition. So the effect of steric hindrance was examined by introducing tert-butyl and 2,4,6-triisopropylphenyl groups on the host macrocycle. Finally, it was found that the association constant between the host and octyl glucoside achieved up to 900,000 /M.

吡啶-苯酚交联大环低聚物具有较强的糖类识别能力。定性研究1H NMR和DFT计算研究表明，糖的识别能力比项目前预期的要强得多。然而，宿主的自聚集对糖的识别是一个严重的问题。因此，通过在宿主大环上引入叔丁基和2,4,6-三异丙基来考察空间位阻的影响。最后发现，宿主与辛基葡萄糖苷的结合常数可达900,000 /M。

项目成果

Selective Binding of D2h-Symmetrical, Acetylene-Linked Pyridine/Pyridone Macrocycles to Maltoside

• DOI: 10.1021/jo2003055
• 发表时间: 2011-05-06
• 期刊: JOURNAL OF ORGANIC CHEMISTRY
• 影响因子: 3.6
• 作者: Abe, Hajime;Chida, Yusuke;Inouye, Masahiko
• 通讯作者: Inouye, Masahiko

Chemistry of Renieramycins. Part 10. Structure of Renieramycin V, A Novel Renieramycin Marine Natural Product Having a Sterol Ether at C-14 position

雷尼尔霉素的化学。

• DOI: 10.3987/com-11-s
• 发表时间: 2012
• 期刊: Heterocycles
• 影响因子: 0.6
• 作者: Naoki Saito;Miho Yoshino;Kornvika Charupant;Khanit Suwanborirux
• 通讯作者: Khanit Suwanborirux

多点水素結合能を有するピリジン-フェノール交互型オリゴマーの合成と性質

具有多点氢键能力的吡啶-苯酚交替低聚物的合成与性能

• 发表时间: 2013
• 作者: 三星 智; 杉山 武晴;原田 明;大石雄基・阿部肇・井上将彦
• 通讯作者: 大石雄基・阿部肇・井上将彦

Synthesis of p-Chloroazacalix[5]arene Pentamethyl Ether: Ring Size-Dependent Desorption of N-Benzyl Groups

对氯氮杂萼[5]芳烃五甲醚的合成：N-苄基的环尺寸依赖性解吸

• DOI: 10.3987/com-12-s
• 发表时间: 2012
• 期刊: Heterocycles
• 影响因子: 0.6
• 作者: T. Kushida;C. Camacho;A. Shuto;S. Irle;M. Muramatsu;T. Katayama;S. Ito;Y. Nagasawa;H. Miyasaka;E. Sakuda;N. Kitamura;Z. Zhou;A. Wakamiya;S. Yamaguchi;Hirohito Tsue
• 通讯作者: Hirohito Tsue

Stabilization of Chiral Helices for Saccharide-Linked Ethynylpyridine Oligomers Possessing a Conformationally Well-Defined Linkage

• DOI: 10.1002/ejoc.201201376
• 发表时间: 2013-03
• 期刊: European Journal of Organic Chemistry
• 影响因子: 2.8
• 作者: Fumihiro Kayamori;H. Abe;M. Inouye