Enantioselective hydrolysis of glycidyl methylphenyl ethers by Botryosphaeria dothidea ZJUZQ007: effect of substitution pattern on enantioselectivity.
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.
Institute of Bioengineering, College of Biological and Environmental Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou, Zhejiang 310014, China.
Yanmin
Y
Sheng
Chun
C
Wei
Zhengfang
Z
Zhang
Shan
S
Wang
Qing
Q
Zhu
D000840:Anisoles / Q000737:chemistry* / Q000378:metabolism*; D001203:Ascomycota / Q000201:enzymology / Q000302:isolation & purification / Q000378:metabolism*; D001711:Biotransformation; D002021:Buffers; D020134:Catalytic Domain; D004851:Epoxide Hydrolases / Q000378:metabolism; D004852:Epoxy Compounds / Q000737:chemistry* / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D008968:Molecular Conformation; D025282:Mycelium / Q000378:metabolism; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature; D013997:Time Factors
D000840:Anisoles; D002021:Buffers; D004852:Epoxy Compounds; C020344:glycidyl ethers; D004851:Epoxide Hydrolases