The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols
The effect of vinyl esters on the enantioselectivity of the lipase-catalysed transesterification of alcohols
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DOI：
10.1016/s0957-4166(01)00083-0
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发表时间：
2001-03-19
影响因子：
--
通讯作者：
Kometani, T
中科院分区：
文献类型：
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作者：
Kawasaki, M;Goto, M;Kometani, T
以一系列3-芳基丙酸乙烯基为酰基供体，研究了洋葱假单胞菌脂肪酶在2-苯基-1-丙醇酯交换反应中的对映选择性。用3-（对碘苯基）或3-（对三氟甲基苯基）丙酸乙烯酯进行对映选择性最强的醇酯交换反应，对映体比E分别为116和138。3-苯基丙酸乙烯基对荧光杆菌和猪胰腺脂肪酶介导的1和pcl催化的几种2-苯基-1烷醇的酯交换反应也有效。1的对映体拆分实际上是通过PCL和3-（对碘苯基）丙酸乙烯酯进行第一次对映选择性酯交换得到(R)-1，然后对映选择性水解得到(S)-1。2001爱思唯尔科学有限公司版权所有。
The enantioselectivity of the lipase from Pseudomonas cepacia (PCL) in the transesterification of 2-phenyl-1-propanol I was studied using a series of vinyl 3-arylpropanoates as acyl donors. The most enantioselective transesterification reaction of the alcohol was attained by using vinyl 3-(p-iodophenyl)- or 3-(p-trifluoromethylphenyl)propanoates, with enantiomer ratios, E, of 116 and 138, respectively. Vinyl 3-phenylpropanoate was also effective for the resolution of 1 mediated by lipases from P. fluorescens and porcine pancreas and for the PCL-catalysed transesterification of several 2-phenyl-1-alkanols. The enantiomeric resolution of 1 was practically carried out by the first enantioselective transesterification using PCL and vinyl 3-(p-iodophenyl)propanoate to afford (R)-1 and then the enantioselective hydrolysis of the resultant ester to afford (S)-1. (C) 2001 Elsevier Science Ltd. All rights reserved.