1999 Fiscal Year Final Research Report Summary
Efficient Synthesis of New Chiral Synthons by Artificial Regulation of Biocatalysis and Development of Optically Active Drugs
| Project/Area Number |
09555288
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Okayama University |
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Principal Investigator |
SAKAI Takashi Okayama University, Faculty of Engineering, Professor, 工学部, 教授 (00170556)
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| Co-Investigator(Kenkyū-buntansha) |
MINAI Masayoshi Sumitomo Chemical Co., Institute of Organic Synthesis, Group Manager, 有機合成研究所, 主任研究員
EMA Tadashi Okayama University, The Graduate School of Natural Science and Technology, Research Associate, 大学院・自然科学研究科, 助手 (20263626)
UTAKA Masanori Okayama University, Faculty of Engineering, Professor, 工学部, 教授 (30033153)
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| Project Period (FY) |
1997 – 1999
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| Keywords | optically active / chiral / asymmetric synthesis / biocatalyst / lipase / subtilisin / reductase / bakers' yeast |
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| Research Abstract |
1. Synthesis of Optically Active Compounds
We designed and synthesized useful chiral synthetic intermediates having an azirine skeleton, a pentafluorophenyl group, a tetraphenylporphyrin moiety and so on. Optically active compounds of these molecules were prepared by lipase- and subtilisin-catalyzed kinetic resolutions or by asymmetric reductions using carbonyl reductases with high enantioselectivities. We found that the diastereofacial selectivity in the nucleophilic addition to azirine derivatives can be controlled by coordination and steric hindrance. We also synthesized new chiral 1, 2-diol and 1, 2 amino alcohol from 2-acyloxy-2-(pentafluorophenyl)acetonitrile.
2. Lipase-catalyzed reactions at very low temperature
(]SY.++.〔ィエD1) and △△SィイD1(〕SY.++.〔ィエD1) values were calculated according to a theoretical equation.
3. Enantioselective reduction using bakers' yeast and purified reductase
Asymmetric reductions using bakers' yeast and carbonyl reductases afforded various optically active alcohols. In general, the reductases purified from bakers' yeast showed higher enantioselectivity than the whole cell of bakers' yeast.
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