有机溶剂中(R)-醇腈酶催化不对称合成(R)-苯乙醇腈  

Asymmetric Synthesis of (R)-Mandelonitrile Catalysed by (R)-Oxynitrilase from Almond in Organic Solvent

作　　者：刘森林[1] 宗敏华[2] 余少文[1] 张小云[1] 邢苗[1] 

机构地区：[1]深圳大学生物工程系,广东深圳518060 [2]华南理工大学生物工程系,广东广州510640

出　　处：《催化学报》2003年第1期7-10,共4页

基　　金：广东省自然科学基金 (980 5 43)资助项目

摘　　要：研究了来源于杏仁的 (R) 醇腈酶在有机溶剂异丙醚中催化苯甲醛与HCN不对称合成 (R) 苯乙醇腈 ,初步探讨了来源于不同杏仁的 (R) 醇腈酶的筛选、最适酶量的确定以及底物HCN与苯甲醛的配比、底物浓度、酶的微环境 pH和反应温度对不对称合成反应的影响 .结果发现 ,来源于苦杏仁的 (R) 醇腈酶优于来源于甜杏仁的 (R) 醇腈酶 .优化的反应条件为 :最适酶量 15 0 g/L,HCN与苯甲醛的配比 2 5 ,苯甲醛浓度 3 0 0mmol/L ,酶的微环境 pH 5 4,反应温度 0～ 5℃ .在该优化反应条件下 ,反应平衡转化率和产物的光学纯度均高达The synthesis of chiral cyanohydrins has attracted growing industrial interest over the last several years. This paper reports the asymmetric synthesis of (R)-mandelonitrile from benzaldehyde and hydrogen cyanide catalysed by (R)-oxynitrilase from almond in organic solvent like isopropyl ether. The conversion of benzaldehyde and enantiomeric excess of (R)-mandelonitrile were determined by gas chromatography on a β-cyclodextrin chiral column. The effects of the enzymes from different sources, optimum enzyme concentration, ratio of HCN to benzaldehyde, substrate concentration, pH of the enzyme microenvironment and reaction temperature on the synthesis of (R)-mandelonitrile were explored. It was found that (R)-oxynitrilase from bitter almond was better than the one from sweet almond. Under the optimum conditions, such as enzyme concentration of 150 g/L, HCN to benzaldehyde molar ratio of 2.5, substrate concentration of 300 mmol/L, enzyme microenvironmental pH of 5.4, and reaction temperature of 0～5 ℃, both the benzaldehyde conversion and enantiomeric excess of the products were as high as 99%.

关 键 词：有机溶剂 催化不对称合成 苯甲醛 氰化氢 (R)-醇腈酶 (R)-苯乙醇腈 

分 类 号：O643.3[理学—物理化学]