Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation
Enzymatic kinetic resolution of hydroxystearic acids: A combined experimental and molecular modelling investigation
复制标题
DOI：
10.1016/j.molcatb.2012.06.017
复制
发表时间：
2012-11-01
影响因子：
--
通讯作者：
Masotti, Lanfranco
中科院分区：
文献类型：
--
作者：
Ebert, Cynthia;Felluga, Fulvia;Masotti, Lanfranco
在醋酸乙烯酯存在下，用脂肪酶CALB和PS对7-、8-、9-和10-羟基硬脂酸（HSA）的外消旋体进行动力学拆分，首次获得了对映体富集的HSA。其中，7-HSA和9-HSA的结果最好，其对映体过量约为55%。对羟基酯进行的相同拆分完全失败。对于酸性底物，Kazlauskas规则和3D-QSAR模型都不能应用，因为这两种模型都侧重于CALB醇袋评估，而不是酰基袋评估。因此，半定量的方法，其结果是根据我们的研究结果，就绝对构型的产品而言。(C)2012爱思唯尔有限公司版权所有。
Enantioenriched 7-, 8-, 9-, and 10-hydroxystearic acids (HSA) were obtained, for the first time, by kinetic resolution of their racemates with lipases CALB and PS, in the presence of vinyl acetate. Among them, the best results were obtained for 7-HSA and 9-HSA, whose enantiomeric excess was around 55%. The same resolutions carried out on the hydroxy esters completely failed. For the acid substrates neither the Kazlauskas' rule nor the 3D-QSAR model could be applied, since both models are focused on the CALB alcohol-pocket evaluation and not on the acyl-pocket one. Therefore, a semiquantitative approach was used, whose results were in accordance with our findings, as far as the absolute configuration of the product is concerned. (C) 2012 Elsevier B.V. All rights reserved.