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研究了水/有机溶剂双相中来源于杏仁的(R)-醇腈酶催化苯甲醛与HCN不对称合成(R )-苯乙氰醇,系统探讨了有机溶剂、水相与有机溶剂相体积比、水相pH值和反应温度对反 应速度、转化率和产物光学纯度的影响. 结果表明,上述因素对醇腈酶促不对称合成(R) -苯乙氰醇反应均有显著影响. 异丙醚为该反应最好的有机溶剂,水相与有机溶剂相体积比 以1/2为宜,适宜的pH值为3.4,最佳反应温度为0~5 ℃. 在该优化反应条件下,反应转化率 和产物的光学纯度均高达99%以上.

The asymmetric synthesis of (R)-mandelonitrile from benzaldehyde and hydrog en cyanide using (R)-oxynitrilase from bitter almond in water/organic solve nt biphase systems was studied. The effects of organic solvents, volume ratio of water phase to organic phase, pH value of aqueous phase and reaction temperatur e on the initial reaction rate, the final conversion and enantiomeric purity of the product were explored. All above mentioned facts had important effects on th e reaction. Diisopropyl ether is found to be the best organic solvent for the re action. The optimum volume ratio of water phase to organic phase, pH and reactio n temperature are 1/2, 3.4 and 0~5 ℃ respectively for the reaction. Under the se conditions, both the conversion rate and enantiomeric excess are as high as 99%.

参考文献

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[6] Bauer M;Griengl H;Steiner W .Parameters influencing stability and activity of a S-hydroxynitrile lyase from Hevea brasiliensis in two-phase systems.[J].Enzyme and Microbial Technology,1999(8/9):514-522.
[7] Roos J;Effenberger F .[J].Tetrahedron:Asymmetry,1999,10(14):2817.
[8] HanS;Lin G;Li Z .[J].Tetrahedron:Asymmetry,1998,9(11):1835.
[9] Lin G;Han S;Li Z .[J].Tetrahedron,1999,55(12):3531.
[10] Laane C;Boeren S;Vos K et al.[J].Biotechnology and Bioengineering,1987,30(01):81.
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[18] Griengl H.;Pochlauer P.;Schmidt M.;Shi NY. Zabelinskaja-Mackova AA.;Klempier N. .Enzyme catalysed formation of (S)-cyanohydrins derived from aldehydes and ketones in a biphasic solvent system[J].Tetrahedron,1998(48):14477-14486.
[19] Laane C;Boeren S;Vos K .[J].Biotechnology and Bioengineering,1987,30(01):81.
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[21] Effenberger F;Angew Chem .[J].Int Ed Engl,1994,33(15):1555.
[22] Griengl H;Hickel A;Johnson D V.[J].Chemical Communications,1997(20):1933.
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