Synthesis of naturally occurring β-D-glycopyranosicle based on a combination of immobilized β-glucosidase and metal catalyst

基于固定化β-葡萄糖苷酶和金属催化剂的组合合成天然存在的β-D-吡喃葡萄糖苷

• 批准号: 18590019
• 负责人: AKITA Hiroyuki
• 金额: $ 2.57万
• 依托单位: Toho University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2006
• 资助国家: 日本
• 起止时间: 2006 至 2007
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-18590019/
• 关键词: β-glucosidase; chemoenzvmatic elucosidation; naturally occurring glucoside; biocatalyst; total synthesis; immobilized enzyme; 酵素化学的配糖化

For the purpose of synthesis of naturally occurring β-D-glucopyranoside, direct β-glucosidation for the many kinds of functionalized primary alcohol in the presence of D-glucose using native or immobilized β-glucosidase (EC 3.2.1.21) from almonds under kinetically or equilibrium controlled condition was carried out. The utilization of high concentration of the alcohol acceptors using the immobilized enzyme gave the corresponding [β-D-glucopyranosides, which were converted to naturally occurring β-D-glucopyranosides. Moreover, allyl (β-D-glucopyranoside obtained based on direct β-glucosidation between allyl alcohol and D-glucose using the immobilized β-glucosidase was converted to the corresponding tetraacetate, which was subjected to the Pd(II)-catalyzed Mizoroki-Heck type reaction with the substituted arylboronic acid congeners to afford the naturally occurring phenylpropenoid β-D-glucopyranosides. In the same way, the Pd(II)-catalyzed Mizoroki-Heck type reaction of allyl 6-O-glycosyl-β-D-glucopyranosides with the substituted arylboronic acid congeners gave the naturally occurring phenylpropenoid 6-O-glycosyl-β-D- glucopyranosides.

为了合成天然存在的β- d -葡萄糖苷，在d -葡萄糖存在下，利用天然或固定化的杏仁β-葡萄糖苷酶（EC 3.2.1.21）在动力学或平衡控制条件下，对多种功能化伯醇进行了直接β-葡萄糖苷化。固定化酶利用高浓度的醇受体得到相应的β- d -葡萄糖苷，并将其转化为天然存在的β- d -葡萄糖苷。此外，利用固定化β-葡萄糖苷酶将烯丙醇与d -葡萄糖直接β-葡萄糖苷化得到烯丙基β- d -葡萄糖苷转化为相应的四乙酸酯，并与取代的芳基硼酸同源物发生Pd（II）催化Mizoroki-Heck型反应，生成天然存在的苯丙烯类β- d -葡萄糖苷。同样，Pd（II）催化的烯丙基6- o -糖基-β- d -葡萄糖苷与取代的芳基硼酸同族物的Mizoroki-Heck型反应得到天然存在的苯丙烯基6- o -糖基-β- d -葡萄糖苷。

项目成果

Synthesis of naturally occurring β-D-glucopyranoside based on enzymatic β-glycosidation

• DOI: 10.1016/j.molcatb.2006.01.031
• 发表时间: 2006-05-19
• 期刊: JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC
• 作者: Akita, H;Kawahara, E;Kato, K
• 通讯作者: Kato, K

Synthesis of naturally occurring β-D-glucopyranoside based on -

基于 - 的天然存在的 β-D-吡喃葡萄糖苷的合成

• 发表时间: 2006
• 期刊: J. Hol. Cat. B : Enzymatic 40
• 作者: 秋田 弘幸;他3名;秋田弘幸 他3名
• 通讯作者: 秋田弘幸 他3名

Future directions in biocatalysis

生物催化的未来方向

• 发表时间: 2007
• 作者: Takanori Murakami;Kazufusa Yamazaki;Atsushi Wakamiya;Shigehiro Yamaguchi;K.Takahashi;T. Kubo;Tomoko Matsuda (Editor)
• 通讯作者: Tomoko Matsuda (Editor)