Multistep conversion of cresols by phenol hydroxylase and 2,3-dihydroxy-biphenyl 1,2-dioxygenase

doi:10.1007/s11783-013-0616-y

Front.Environ.Sci.Eng.

2014, Vol. 8

Issue (4) : 539-546 https://doi.org/10.1007/s11783-013-0616-y

RESEARCH ARTICLE

Multistep conversion of cresols by phenol hydroxylase and 2,3-dihydroxy-biphenyl 1,2-dioxygenase

Shengnan SHI¹,Fang MA^1,^*(

),Tieheng SUN¹,Ang LI¹,Jiti ZHOU²,Yuanyuan QU^2,^*(

)

1. State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China
2. Key Laboratory of Industrial Ecology and Environmental Engineering (Ministry of Education), School of Environmental Science and Technology, Dalian University of Technology, Dalian 116024, China

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Abstract

A multistep conversion system composed of phenol hydroxylase (PH_IND) and 2,3-dihydroxy-biphenyl 1,2-dioxygenase (BphC_LA-4) was used to synthesize methylcatechols and semialdehydes from o- and m-cresol for the first time. Docking studies displayed by PyMOL predicted that cresols and methylcatechols could be theoretically transformed by this multistep conversion system. High performance liquid chromatography mass spectrometry (HPLC-MS) analysis also indicated that the products formed from multistep conversion were the corresponding 3-methylcatechol, 4-methylcatechol, 2-hydroxy-3-methyl-6-oxohexa-2,4-dienoic acid (2-hydroxy-3-methyl-ODA) and 2-hydroxy-5-methyl-6-oxohexa-2,4-dienoic acid (2-hydroxy-5-methyl-ODA). The optimal cell concentrations of the recombinant E. coli strain BL21 (DE3) expressing phenol hydroxylase (PH_IND) and 2,3-dihydroxy-biphenyl 1,2-dioxygenase (BphC_LA-4) and pH for the multistep conversion of o- and m-cresol were 4.0 (g·L^-1 cell dry weight) and pH 8.0, respectively. For the first step conversion, the formation rate of 3-methylcatechol (0.29 μmol·L^-1·min^-1·mg^-1 cell dry weight) from o-cresol was similarly with that of methylcatechols (0.28 μmol·L^-1·min^-1·mg^-1 cell dry weight) from m-cresol by strain PH_IND. For the second step conversion, strain BphC_LA-4 showed higher formation rate (0.83 μmol·L^-1·min^-1·mg^-1 cell dry weight) for 2-hydroxy-3-methyl-ODA and 2-hydroxy-5-methyl-ODA from m-cresol, which was 1.1-fold higher than that for 2-hydroxy-3-methyl-ODA (0.77 μmol·L^-1·min^-1·mg^-1cell dry weight) from o-cresol. The present study suggested the potential application of the multistep conversion system for the production of chemical synthons and high-value products.

Keywords multistep conversion cresols phenol hydroxylase 2 3-dihydroxybiphenyl 1 2-dioxygenase methylcatechols

Corresponding Author(s): Fang MA

Issue Date: 11 June 2014

Cite this article:

Shengnan SHI,Fang MA,Tieheng SUN, et al. Multistep conversion of cresols by phenol hydroxylase and 2,3-dihydroxy-biphenyl 1,2-dioxygenase[J]. Front.Environ.Sci.Eng., 2014, 8(4): 539-546.

URL:

https://academic.hep.com.cn/fese/EN/10.1007/s11783-013-0616-y
https://academic.hep.com.cn/fese/EN/Y2014/V8/I4/539

Fig.1 Interactions between PH_IND and BphC_LA-4 component with o- and m-cresol, and methylcatechols, respectively. Red spheres represent for diiron. (a) o-cresol; (b) m-cresol; (c) 3-methylcatechol; (d) 4-methylcatechol

Fig.2 Mass spectra of products formed from multistep conversion by strains PH_IND and BphC_LA-4. (a) products of o-cresol multistep conversion; (b) products of m-cresol multistep conversion

Fig.3 Effect of strain concentration on multistep conversion. The first step conversion (a): 3-methylcatechol (?) formed from o-cresol, 3-methylcatechol (◆) formed from m-cresol and 4-methylcatechol (?) formed from m-cresol; The second step conversion (b): 2-hydroxy-3-methyl-ODA (n) formed from 3-methylcatechol, 2-hydroxy-3-methyl-ODA (?) formed from 3-methylcatechol and 2-hydroxy-5-methyl-ODA (●) formed from 4-methylcatechol

Fig.4 Time course of o- and m-cresol multistep conversion. The first step conversion was on the left side, the second step conversion was on the right. (a) concentration of o-cresol (n), 3-methylcatechol (l), 2-hydroxy-3-methyl-ODA (π); (b) concentration of m-cresol (?), 3-methylcatechol (l), 4-methylcatechol (u), 2-hydroxy-3-methyl-ODA (π) 2-hydroxy-5-methyl-ODA (?)

Fig.5 Effect of pH on multistep conversion. (a) 3-methylcatechol (n) formed from o-cresol, 3-methylcatechol (?) formed from m-cresol and 4-methylcatechol (●) formed from m-cresol; (b) 2-hydroxy-3-methyl-ODA (?) formed from 3-methylcatechol, 2-hydroxy-3-methyl-ODA (◆) formed from 3-methylcatechol and 2-hydroxy-5-methyl-ODA (?) formed from 4-methylcatechol

Fig.6 Effect of glucose concentrations on the first step conversion: 3-methylcatechol (n) formed from o-cresol, 3-methylcatechol (?) formed from m-cresol and 4-methylcatechol (●) formed from m-cresol

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