2002 Fiscal Year Final Research Report Summary
enantioselective biaryl coupling catalyzed by enzymes
| Project/Area Number |
12672057
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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 | University of Shizuoka |
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Principal Investigator |
TAKEMOTO Masumi University of Shizuoka, School of Pharmaceutical Sciences lecturer, 薬学部, 講師 (70117779)
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| Project Period (FY) |
2000 – 2002
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| Keywords | enzymes / plant cell culture / Camellia sinensis cell culture / atropisomer / biaryl coupling / 2-naphthol / peroxidase / oxidative coupling |
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| Research Abstract |
1,1'-Binaphthalene derivatives have been widely used in organic synthesis as chirality inducers for highly stereoselective reactions. Enantiomerically pure binaphthyl derivatives have been prepared by optical resolution of racemic compounds, an intermolecular Ullmann coupling, a nucleophilic aromatic substitution, an oxidative dimerization of 2-naphthols with copper amine complexes as oxidant or electrocatalytic oxidative coupling. Recently we have found that camellia sinensis cell culture is an efficient source of peroxidase (POD) enzymes. We have established C. sinensis cell culture systems with high POD activity and applied enantioselective oxidative coupling of 2-naphthol derivatives by C. sinensis cell culture. A novel enantioselective oxidative coupling of 2-naphthol derivatives by C. sinensis cell culture with high POD activity can be achieved in this work. It is noteworthy that moderate to good ee values were obtained for simple substrates such as 2-naphthol (CY 47%, OY 59%) that are difficult substrates for enantioselective oxidative coupling reaction.
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