表面活性剂介入酵母细胞催化芳香酮的对映选择性还原  

Enantioselective Reduction of Aromatic Ketones Catalyzed by Yeast Cells in the Presence of Surfactants

作　　者：杨芬 刘湘 

机构地区：[1]江南大学化学与材料工程学院,江苏无锡214122

出　　处：《精细化工》2014年第5期565-569,658,共6页Fine Chemicals

摘　　要：以酵母细胞催化4'-氯苯乙酮合成(S)-1-4'-氯苯基乙醇为模型反应,研究了十六烷基三甲基溴化铵、十二烷基硫酸钠和壬基酚聚氧乙烯醚系列表面活性剂对酵母细胞催化4'-氯苯乙酮对映选择性还原反应的影响。结果表明,向反应体系中加入表面活性剂可明显提高4'-氯苯乙酮的转化率,而对产物(S)-1-4'-氯苯基乙醇对映体过量值的影响极小,壬基酚聚四氧乙烯醚(NP-4)是最合适的添加剂。此外,还考察了NP-4对酵母细胞催化系列芳香酮对映选择性还原反应的影响,结果表明,NP-4对产物(S)-1-芳基乙醇的对映体过量值几乎没影响,但对底物芳香酮转化率均有明显的提高,同时还发现底物转化率的提高幅度与芳香环上取代基的电子效应有关,取代基供电子能力越强越有利于底物转化率的增加。In aqueous buffer system containing surfactants （cetyhrimethyl ammonium bromide or sodium dodecyl sulfate or nonylphenol polyoxyethylene ether ）, the enantioselective reduction of 4＇- chloroacetophenone to its corresponding chiral alcohol （S）-1-4＇-chlorophenyl ethanol catalyzed by yeast cells was investigated. The results indicate that the conversion of 4＇-chloroacetophenone was distinctly improved and the enantiomeric excess of the product （S）-1-4＇-chlorophenyl ethanol was barely changed when the surfactants were added to the system. Nonylphenol polytetraoxyethylene ether （NP -4） was the most appropriate additive among the surfactants added. In addition, the influence of nonionic surfactant NP -4 on the enantioselective reduction of aromatic ketones was studied. The results show that the enantiomeric excesses of the product （S）-1-aryl ethanol had little change and the conversion of all aromatic ketones was significantly enhanced in the presence of NP -4. It was also found that the increase of the substrate conversion was relevant to the electronic effect of the substituents on the aromatic ring. The stronger electron-donating capacity of the substituents was more conducive to the increase of the substrate conversion.

关 键 词：芳香酮 对映选择性还原 酵母细胞 取代基效应 表面活性剂 

分 类 号：TQ423.93[化学工程]