Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone

Journal of Bacteriology
Ying TaoThomas K Wood

Abstract

Wild-type toluene 4-monooxygenase (T4MO) of Pseudomonas mendocina KR1 oxidizes toluene to p-cresol (96%) and oxidizes benzene sequentially to phenol, to catechol, and to 1,2,3-trihydroxybenzene. In this study T4MO was found to oxidize o-cresol to 3-methylcatechol (91%) and methylhydroquinone (9%), to oxidize m-cresol and p-cresol to 4-methylcatechol (100%), and to oxidize o-methoxyphenol to 4-methoxyresorcinol (87%), 3-methoxycatechol (11%), and methoxyhydroquinone (2%). Apparent Vmax values of 6.6 +/- 0.9 to 10.7 +/- 0.1 nmol/min/ mg of protein were obtained for o-, m-, and p-cresol oxidation by wild-type T4MO, which are comparable to the toluene oxidation rate (15.1 +/- 0.8 nmol/min/mg of protein). After these new reactions were discovered, saturation mutagenesis was performed near the diiron catalytic center at positions I100, G103, and A107 of the alpha subunit of the hydroxylase (TmoA) based on directed evolution of the related toluene o-monooxygenase of Burkholderia cepacia G4 (K. A. Canada, S. Iwashita, H. Shim, and T. K. Wood, J. Bacteriol. 184:344-349, 2002) and a previously reported T4MO G103L regiospecific mutant (K. H. Mitchell, J. M. Studts, and B. G. Fox, Biochemistry 41:3176-3188, 2002). By using o-cresol and o-m...Continue Reading

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Citations

Mar 3, 2005·Applied Microbiology and Biotechnology·Ying TaoThomas K Wood
Nov 9, 2010·Applied Microbiology and Biotechnology·Lydie CoulombelKevin E O'Connor
Oct 1, 2010·Indian Journal of Microbiology·Mingxi HuYongjun Feng
May 8, 2007·Applied and Environmental Microbiology·Jintae LeeThomas K Wood
Aug 21, 2007·Applied and Environmental Microbiology·Elena BorodinaJ Colin Murrell
Aug 17, 2010·Applied and Environmental Microbiology·Moran BroukAyelet Fishman
Jan 15, 2008·Applied and Environmental Microbiology·Roi FeingerschAyelet Fishman
Dec 17, 2008·Applied and Environmental Microbiology·Eugenio NotomistaAlberto Di Donato
May 26, 2009·Applied and Environmental Microbiology·Janna ShainskyAyelet Fishman
Apr 7, 2006·Applied and Environmental Microbiology·Joanna DomkaThomas K Wood
Jun 9, 2006·Microbiology and Molecular Biology Reviews : MMBR·Jorge LalucatNorberto J Palleroni
Jan 16, 2007·Environmental Microbiology·Joanna DomkaThomas K Wood
Jun 18, 2005·Current Opinion in Biotechnology·Rebecca E Parales, Jayna L Ditty
Aug 19, 2014·The Science of the Total Environment·Seungjin KimJinwook Chung
Jan 15, 2010·FEMS Microbiology Reviews·Jin-Hyung Lee, Jintae Lee
Oct 30, 2016·Metabolic Engineering·Shuchi H DesaiShota Atsumi
May 20, 2008·Advances in Applied Microbiology·R E ParalesJ L Ditty
Sep 17, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Ambica KejriwalAchintesh N Biswas
Dec 22, 2006·Biotechnology Journal·Javier F Chaparro-RiggersAndreas S Bommarius
Jun 6, 2008·The ISME Journal·Jintae LeeThomas K Wood
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Jan 1, 2013·Biomolecules·Francesca Valetti, Gianfranco Gilardi
May 7, 2014·The Journal of Physical Chemistry. B·Ali HosseiniVictor Guallar

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