Multistep conversion of para-substituted phenols by phenol hydroxylase and 2,3-dihydroxybiphenyl 1,2-dioxygenase.
A multistep conversion system of para-substituted phenols by recombinant phenol hydroxylase (PH(IND)) and 2,3-dihydroxybiphenyl 1,2-dioxygenase (BphC(LA-4)) was constructed in this study. Docking studies with different para-substituted phenols and corresponding catechols inside of the active site of PH(IND) and BphC(LA-4) predicted that all the substrates should be transformed. High-performance liquid chromatography-mass spectrometry analysis showed that the products of multistep conversion were the corresponding para-substituted catechols and semialdehydes. For the first-step conversion, the formation rate of 4-fluorocatechol (0.39 μM/min/mg dry weight) by strain PH(IND) hydroxylation was 1.15, 6.50, 3.00, and 1.18-fold higher than the formation of 4-chlorocatechol, 4-bromocatechol, 4-nitrocatechol, and 4-methylcatechol, respectively. For the second-step conversion, the formation rates of semialdehydes by strain BphC(LA-4) were as follows: 5-fluoro-HODA>5-chloro-HODA>2-hydroxy-5-nitro-ODA>5-bromo-HODA>2-hydroxy-5-methyl-ODA. The present study suggested that the multistep conversion by both ring hydroxylase and cleavage dioxygenase should be potential in the synthesis of industrial precursors and provide a novel avenue in the wastewater recycling treatment.
Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education, China), School of Environmental Science and Technology, Dalian University of Technology, Dalian 116024, China. qyy@dlut.edu.cn
Yuanyuan
Y
Qu
Shengnan
S
Shi
Qiao
Q
Ma
Chunlei
C
Kong
Hao
H
Zhou
Xuwang
X
Zhang
Jiti
J
Zhou
D002396:Catechols / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D049308:Dioxygenases / Q000378:metabolism*; D006899:Mixed Function Oxygenases / Q000378:metabolism*; D008956:Models, Chemical; D010636:Phenols / Q000378:metabolism*
D002396:Catechols; D010636:Phenols; C018599:4-methylcatechol; C040660:4-bromocatechol; C072305:4-fluorocatechol; D006899:Mixed Function Oxygenases; D049308:Dioxygenases; C074272:2,3-dihydroxybiphenyl oxygenase; C022336:phenol 2-monooxygenase; C038861:4-chlorocatechol