Resolution of racemic glycidyl (o, m, p)-methylphenyl ethers by using a newly isolated Botryosphaeria dothidea ZJUZQ007 with epoxide hydrolase activity affords enantiopure epoxides with enantiomeric excesses (e.e.(s)) of 91-99% and enantiomeric ratios (E) of 18.1 to 48.6. The (R)-enantiomer was obtained from rac-glycidyl (o or m)-methylphenyl ethers whereas the (S)-epoxides was obtained from glycidyl p-methylphenyl ether. Substitution pattern of the methyl group exerted effects both on configurations of the remaining epoxides and enantioselectivities of epoxide hydrolase. The observations were explained by enzyme-substrate docking studies. It is the first example showing that for kinetic resolution of glycidyl methylphenyl ethers, fungal species of B. dothidea was applied.

译文

:通过使用新分离的具有环氧化物水解酶活性的多孢杆菌(Botryosphaeria dothidea)ZJUZQ007拆分外消旋的缩水甘油基(o,m,p)-甲基苯基醚,得到对映体纯的环氧化物,对映体过量(ee)为91-99%,对映体比率(E)为18.1至48.6。 (R)-对映异构体是从外消旋缩水甘油基(o或m)-甲基苯基醚获得的,而(S)-环氧化物是从缩水甘油基对甲基苯基醚获得的。甲基的取代模式对剩余的环氧化物的构型和环氧化物水解酶的对映选择性都起作用。酶底物对接研究解释了这些观察结果。这是第一个实例,表明对于缩水甘油基甲基苯基醚的动力学拆分,应用了双歧双歧杆菌的真菌物种。

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