发明公开
EP1358173A1 VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEN, PROPARGYLISCHEN, TERMINALEN EPOXIDEN
审中-公开
用于生产光学活性的,丙炔,环氧化物终端
- 专利标题: VERFAHREN ZUR HERSTELLUNG VON OPTISCH AKTIVEN, PROPARGYLISCHEN, TERMINALEN EPOXIDEN
- 专利标题(英): Method for producing optically active, propargylic terminal epoxides
- 专利标题(中): 用于生产光学活性的,丙炔,环氧化物终端
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申请号: EP02706661.2申请日: 2002-02-02
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公开(公告)号: EP1358173A1公开(公告)日: 2003-11-05
- 发明人: SCHUBERT, Thomas, A. , HUMMEL, Werner , MÜLLER, Michael
- 申请人: FORSCHUNGSZENTRUM JÜLICH GMBH
- 申请人地址: Wilhelm-Johnen-Strasse 52425 Jülich DE
- 专利权人: FORSCHUNGSZENTRUM JÜLICH GMBH
- 当前专利权人: FORSCHUNGSZENTRUM JÜLICH GMBH
- 当前专利权人地址: Wilhelm-Johnen-Strasse 52425 Jülich DE
- 优先权: DE10105866 20010209
- 国际公布: WO02064579 20020822
- 主分类号: C07D301/24
- IPC分类号: C07D301/24 ; C07D303/02 ; C12P17/02
摘要:
The invention relates to a method for enantioselective representation of optically active, propargylic, terminal epoxides. According to the invention, in a first step of the inventive method, compounds of formula I are reacted with an alcoholdehydrogenase which preferably originates from horse liver or thermophilic microorganisms (e.g. thermoanaerobium brockii or thermoanaerobacter ethanolicus) or from Lactobacillus and is recombinantly overexpressed in Escherichia coli, in the presence of NAD (P) H. During said reaction, the oxogroup is enantioselectively reduced. Since (S) selective and (R) selective oxidoreductases can be used, the synthesis of both enantiomers is possible. Representation of both enantiomers using the same enzyme is achieved with alkoholdehydrogenase from Lactobacillus brevis, since said compounds react with R1 = H and compounds with R1 = H to form alcohols having an opposite configuration. In the second step of the method, the α-halogenated alcohol is transformed into an enantiomer pure epoxide by means of a base.
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