以苯乙酮为模型底物,研究了水相体系中酵母细胞催化前手性芳香酮不对称还原生成相应手性醇的反应特性. 实验发现,酵母细胞催化苯乙酮不对称还原的产物以(S)-α-苯乙醇为主,反应的立体选择性很高,(S)-α-苯乙醇的对映体过量值可达99%左右. 在pH为7~8, 酵母细胞用量为0.2 g/ml的条件下能获得较高的产物收率(可达35%左右). 酵母细胞能选择性地氧化(S)-α-苯乙醇,而留下(R)-α-苯乙醇. 在反应体系中加入合适的吸附树脂,可以降低底物和产物对细胞的毒害作用,显著提高反应底物的初始浓度,从而提高产物收率.
参考文献
[1] | Srebnik M;Ramachandran P V;Brown H C .[J].Journal of Organic Chemistry,1988,53(13):2916. |
[2] | 张毅立;廖建;陈代谟;孙洪涛 .[J].化学研究与应用,1999,11(05):480. |
[3] | Shimizu S.;Kita K.;Kataoka M. .Chiral alcohol synthesis with yeast carbonyl reductases[J].Journal of molecular catalysis, B. Enzymatic,1998(1/4):321-325. |
[4] | Rosen T;Heathcock C H .[J].Journal of the American Chemical Society,1985,107(12):3731. |
[5] | Touchard F;Bernard M;Fache F;Lemaire M .[J].Journal of Molecular Catalysis A:Chemical,1999,140(01):1. |
[6] | Flores-López C Z;Flores-López L Z;Aguirre G;Hellberg L H,Parra-Hake M,Somanathan R .[J].Journal of Molecular Catalysis A:Chemical,2004,215(1-2):73. |
[7] | Hage A.;Field JA.;Schipper D.;Wijnberg JBPA.;Kamer PCJ. Reek JNH.;van Leeuwen PWNM.;Wever R.;Schoemaker HE.;Petra DGI. .Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: complementary approaches[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,2001(7):1025-1034. |
[8] | Kroutil W;Mang H;Edegger K;Faber K .[J].Current Opinion in Chemical Biology,2004,8(02):120. |
[9] | 杨忠华,姚善泾.水相中酵母细胞催化4-氯乙酰乙酸乙酯不对称还原反应[J].催化学报,2004(06):434-438. |
[10] | Yadav JS.;Nanda S.;Reddy PT.;Rao AB. .Efficient enantioselective reduction of ketones with Daucus carota root[J].The Journal of Organic Chemistry,2002(11):3900-3903. |
[11] | Yang Zh-H;Yao Sh-J;Lin D-Q .[J].Industrial and Engineering Chemistry Research,2004,43(16):4871. |
[12] | 杨忠华,姚善泾.有效控制活性酵母细胞催化β-羰基酯不对称还原反应立体选择性的研究[J].催化学报,2004(10):805-808. |
[13] | Roffler S R;Blanch H W;Wilke C R .[J].Trends in Biotechnology,1984,2(05):129. |
[14] | Roddick FA;Britz ML;ROYAL MELBOURNE INST TECHNOL DEPT CHEM & MET ENGN MELBOURNE VIC 3001 AUSTRALIA. .Production of hexanoic acid by free and immobilised cells of Megasphaera elsdenii: Influence of in-situ product removal using ion exchange resin[J].Journal of Chemical Technology & Biotechnology,1997(3):383-391. |
[15] | Prelog V .[J].Helvetica Chimica Acta,1953,36(39):308. |
[16] | Griffin DR;Gainer JL;Carta G .Asymmetric ketone reduction with immobilized yeast in hexane: Biocatalystdeactivation and regeneration[J].Biotechnology Progress,2001(2):304-310. |
[17] | 杨忠华 .[D].杭州:浙江大学,2005. |
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