Synthesis of naturally occurring β-D-glycopyranosicle based on a combination of immobilized β-glucosidase and metal catalyst
| Project/Area Number |
18590019
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Toho University |
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Principal Investigator |
AKITA Hiroyuki Toho University, Faculty of Phannaceutical Sciences, Professor (60087525)
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| Co-Investigator(Kenkyū-buntansha) |
KATO Keisuke Toho University, Faculty of Pharmaceutical Sciences, Lecturer (80276609)
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| Project Period (FY) |
2006 – 2007
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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥4,020,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥420,000)
Fiscal Year 2007: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2006: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | β-glucosidase / chemoenzvmatic elucosidation / naturally occurring glucoside / biocatalyst / total synthesis / immobilized enzyme / 酵素化学的配糖化 |
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| Research Abstract |
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.
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Report
(3 results)
Research Products
(13 results)
