1998 Fiscal Year Final Research Report Summary
Exploitation of Diastereo-Facial Selective Carbon-Carbon Bond Formation Reaction by the Use of Enzyme
Project/Area Number |
09672182
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Research Category |
Grant-in-Aid for Scientific Research (C)
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Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical pharmacy
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Research Institution | The Institute of physical and Chemical Research (RIKEN) |
Principal Investigator |
SHIMAGAKI Masayuki RIKEN,Synthetic Organic Chemistry Laboratory, Scientist, 有機合成化学研究室, 先任研究員 (10087611)
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Project Period (FY) |
1997 – 1998
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Keywords | stereoselective reaction / carbon-carbon bond formation / immobilized polymer / dendrimer model / functionalized polymer / tetraol / immobilized polymer / tetraol |
Research Abstract |
For a long and long ago, it is a big dream for organic chemists that we intend to obtain optically pure compounds from optically inactive substances or materials with no asymmetric center by making carbon-carbon bond and it is also a big challenge for organic chemistry. But there are few investigations in which these important reactions of biosyntheses are extended to organic synthesis. Especially, there are very few studies on carbon-carbon bond formation reactions. We have investigated for more than ten years on these studies. Of all, we found that dihydroxy acetone phosphate (DHAP) and aldehydes with electron withdrawing group at 2-position in the presence of fructose-l, 6-diphosphate (FDP) aldolase gave corresponding aldols not only controlling the center of two carbon units at the connecting carbon-carbon bond but also controlling the carbon at the withdrawing group of aldehydes, totally controlling the center of three carbon units. The reaction conditions by using aldehyde with chlorine group at 2-position and DHAP in the presence of FDP aldolase was examined to find that the corresponding aldol was obtained in 70% yield. But there is no reproducibility in the reaction. So, the enzyme was intended to immobilize with dendrimers which have been strong attention to their physical properties for physicists. The method of formation of novel functionalized polymers by introducing appropriate enzymes was investigated, funcitonalized groups to the outer shell of dendrimer cores as the models. At first, the examination of introduction of tetraol, one of dendrimer cores, was performed from nitromethane via tetracarboxylic acid and was succeeded to synthesize it in 67% yield by four steps. It was tried to couple with Boc alanine, a protected amino acid at N-terminal with Boc to be found a coupling product, an objective functionalized dendrimer model in 48% yield.
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Research Products
(6 results)