面包酵母催化不对称还原EOPB反应中的溶剂效应.pdf

第23卷第2期
化学研究与应用
Vol 23, No. 2
2011年2月
Chemical Research and Application
Fecb.,2011
文章编号:1004-1656(2011)02-0145-07
面包酵母催化不对称还原EOPB反应中的溶剂效应
石玉刚“,励建荣,唐琼
浙江工、商大学食品与生物工程学院浙江省食品安全重点实验室,浙江杭州310035)
摘要:研究了非水介质中面包酵母催化不对称还原2-氧代4-苯基丁酸乙酯(EOPB)合成手性2-羟基4-苯36
基丁酸乙酯(FHPB)的反应。乙醚体系中湿酵母(WB)催化6rmol?I:FOPB合成(R)-FHPB的e.e.值较之
于干酵母(DB)提高了近19%,但WB稳定性较差。DB催化该反应的立体选择性随溶剂logP(0.82-3.2)的
增加而降低,反应从相同logP值(3.2)的二甲苯转换至环己烷后产物构型由R转为S,经有机溶剂预处理后
酵母醇脱氢酶(YADH)的紫外及荧光光谱的特征变化表明溶剂分子极性与结构的协同作用下酵母催化行为
发生了改变。
关键词:面包酵母;不对称还原;手性;2-羟基4-苯基丁酸乙酯
中图分类号:0621.34文献标识码:A
Effect of organic solvents on asymmetric reduction of
ethyl-2-0x0-4-phenylbutyrate mediated by saccharomyces cerevisiae
SHI Yu-gang, LI Jian-rong, TANG Qiong
(School of Food Science and Biotechnolog hejiang Gon shang University, Food Safety Key Tab of Zhejiang Province
Hangzhou 310035, China
Abstract The asymmetric reduction of t hyl-2-x0-4-penl u rate(EOPB catalyzed by saccharomyces cerevisiae in organic
hase o synthesize chiral ethl-2-hydrox -4-phen butyrate(EHPB was investigated. In diethyl ether with the initial EOPB
concentration of 6 mmol I,, the e. e(R)-EHPB was increased 19% by using wet bakers yeast(WB) as biocatalyst compared
to that by dry bakers yeast (DB). However, the catalytic activity and stability of WB was lower than that of D. The
enantseeci of e e o e( HP was uce with the inerease of the og P value(0.82-3.2) of employed
organic solvents. Although dimethylbenzene and cyclohexane had the same log p value(3.2), the enantioselectivity of the
reduction was reversed from R to S when dimethylbenzene was in place of cyclo exane as reaction media Significant chan
observed in the UV absorption and fluorescence spectrum of the YADH from the yeast pretreated by the solvents. These facts
indicated that the synergistic effect of solvent polarity and its spatial structure ed to the change of the catalytic behavior of baker
: ast
Key words: bakers yeast; asymmetric reduction; chirality; ethyl 2-hydroxy-4-phenylbutyrate
收稿日期:2010-05-17;修回日期:2010-1107
基金项目:浙江省自然科学基金(Y4100762)资助项目;渐江省教育厅科研项目(Y201016439)资助项目;浙江工商大学人オ引进科研基金
09-57)资助项目;200年浙江省大学生科技创新活动计资助
联系人简介:石玉刚(1980-),男,讲师,主要研究方向:绿色化学及功能食品添加剂。Email:yugangshi@126.com