深圳大学学报（理工版）2011，Vol.28Issue(1)：54-59,6.
桃仁醇腈酶促不对称合成含硅(R)-酮氰醇
Asymmetric synthesis of silicon containing(R)-ketone cyanhydrin catalyzed by(R)-hydroxynitrile lyase from peach seed meal
摘要
Abstract
Due to the specific characteristics of silicon atom, organosilicon compounds have attracted growing interest for some years.In the present study, the asymmetric synthesis of optically active (R) -2-trimethylsilyl-2-hydroxyl-ethylcyanide via enantioselective transcyanation of acetyltrimethylsilane with acetone cyanohydrin ( donor of HCN) catalyzed by (R)- hydroxynitrile lyase from defatted peach seed meal in an aqueous/organic biphasic system was successfully carried out.The conversion of acetyltrimethylsilane and enantiomeric excess of (R) -2-trimethylsilyl-2-hydroxyl-ethylcyanide were determined by gas chromatography on a β-cyclodextrin chiral column.The influences of enzyme amount, substrate concentration, organic solvent, the volume ratio of aqueous to organic phase, buffer pH, reaction temperature and substrate structure on the reaction were investigated systematically.Under the optimum conditions including an enzyme amount of 0.6 g, a concentration of acetyltrimethylsilane of 14 mmol/L, an organic solvent of diisopropyl rther, a volume ratio of aqueous to organic phase of 1.5∶10, a buffer pH of 5.0 and a reaction temperature of 30 ℃, both acetyltrimethylsilane conversion and enantiomeric excess of the product were above 99％.Comparative study demonstrates that silicon atom in acetyltrimethylsilane has a great effect on the reaction and both the substrate conversion and the product enantiomeric excess of the transcyanation of acetyltrimethylsilane are much higher than those of its carbon counterpart 3, 3-dimethyl-2-butanone.关键词
醛缩酶/生物催化/不对称合成/桃仁醇腈酶/(R)-酮氰醇/有机硅分类
生物科学引用本文复制引用
刘森林..桃仁醇腈酶促不对称合成含硅(R)-酮氰醇[J].深圳大学学报（理工版）,2011,28(1):54-59,6.基金项目
国家自然科学基金资助项目(20376026) （20376026）
广东省自然科学基金资助项目(000444) （000444）
