脂肪醇族酰基受体对酶法拆分扁桃酸对映体的影响  

Effect of fatty alcohol acyl receptor on enantiomeric resolution of mandelic acid enantiomers by enzymatic method

作　　者：赵泽普 李志刚[1] 杨博[1] ZHAO Zepu;LI Zhigang;YANG Bo(School of Biology and Biological Engineering,South China University of Technology,Guangzhou 510006,China)

机构地区：[1]华南理工大学生物科学与工程学院,广东广州510006

出　　处：《化学反应工程与工艺》2019年第5期416-421,428,共7页Chemical Reaction Engineering and Technology

基　　金：国家自然科学基金面上项目(21776103);广州市科技计划项目(201707010391);广东省普通高校特色创新类项目(2019KTSCX004)。

摘　　要：利用脂肪酶拆分手性酸是目前研究的热点及难点,脂肪醇作为手性拆分中的酰基受体,对选择性具有较大的影响。探究了不同碳链长度的脂肪醇作为酰基受体对扁桃酸对映体的拆分的影响,选取了不同的脂肪醇与扁桃酸在异丙醚中进行酯化反应。结果表明,随着脂肪醇链长增加,选择性呈降低趋势,转化率呈升高趋势。其中中链脂肪醇(碳原子数5~8个的脂肪醇)相比短链脂肪醇(碳原子数小于等于4个的脂肪醇)选择性差别并不大,而转化率明显提升;长链脂肪醇(碳原子数大于等于9个的脂肪醇)选择性较差。在对中链脂肪醇进一步探究中发现,正戊醇作为酰基受体优于其他中链脂肪醇,继而考察了各条件对反应的影响,得到在反应温度30℃,摇床转速200 r/min,加酶量200 mg,底物物质的量之比1:4和反应时间5 h的条件下,扁桃酸戊酯过量值(eep)可以达到70.09%,外消旋转化率达到23.40%。Resolution of chiral acids by lipase is a hot and difficult topic.As acyl receptors in chiral resolution,aliphatic alcohols have great influence on their selectivity.The aim of this study is to investigate the effect of aliphatic alcohols with different carbon chain lengths as acyl receptors on the resolution of mandelic acid enantiomers.Different aliphatic alcohols were selected and esterified with mandelic acid in isopropyl ether.The results showed that with the increase of chain length of aliphatic alcohols,the selectivity decreased and the conversion increased.The selectivity of medium-chain aliphatic alcohols with 5-8 carbon atoms was not significantly different from that of short-chain aliphatic alcohols with 1-4 carbon atoms,but the conversion increased greatly,while the selectivity of long-chain aliphatic alcohols with more than 8 carbon atoms was poor.Among the middle-chain aliphatic alcohols,n-amyl alcohol was superior to the others.The effects of various conditions on the reaction of mandelic acid and n-amyl alcohol were investigated,and the optimal condition was obtained as follows:reaction time 5 h,temperature 30℃,shaking speed 200 r/min,enzyme dosage 200 mg,and the molar ratio of mandelic acid to amyl alcohol 1:4.In this condition,enantiomeric excess of amyl mandelate was 70.09%and conversion was 23.40%.

关 键 词：扁桃酸 脂肪醇 扁桃酸戊酯 脂肪酶 光学拆分 

分 类 号：Q814.9[生物学—生物工程]