A vanillate (4-hydroxy-3-methoxybenzoate)-utilizing bacterium that is unable to utilize p-cresol (4-methylphenol) or 2,4-xylenol (2,4-dimethylphenol) as sole source of carbon and energy was isolated and identified as Pseudomonas fluorescens. The organism employs an inducible hydroxylase (decarboxylating), a fungal mode of attack, rather than a demethylase or methylhydroxylase as the initial step in vanillate metabolism. The product of the initial hydroxylation reaction, methoxyhydroquinone, a derivative that could only be generated with the appropriate groups, hydroxyl and carboxyl, parato each other on the benzene ring, was identified using HPLC analysis. This organism may prove useful in the commercial production of methoxyquinone and methoxyhydroquinone derivatives from renewable resources.
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P. André A. Hatakka K.-E. Eriksson (1980) ArticleTitleVanillic acid metabolism by the white-rot fungus Sporotrichum pulverulentum Archives of Microbiology 125 189–202
R. Benner M.A. Moran R.E. Hodson (1986) ArticleTitleBiogeochemical cycling of lignocellulosic carbon in marine and freshwater ecosystems relative contributions of procaryotes and eucaryotes Limnology and Oceanography 31 89–100
F.-H. Bernhardt H. Pachowsky H. Staudinger (1975) ArticleTitleA 4-methoxybenzoate O-demethylase from Pseudomonas putida– a new type of monooxygenase system European Journal of Biochemistry 57 241–256
J.A. Buswell P. Ander B. Petterson K.-E. Eriksson (1979) ArticleTitleOxidative decarboxylation of vanillic acid by Sporotrichum pulverulentum FEBS Microbiology Letters 103 98–101
J.A. Buswell K.-E. Eriksson P. Ander B. Petterson (1981) ArticleTitlePurification and partial characterisation of vanillate hydroxylase (decarboxylating) from Sporotrichum pulverulentum Journal of Chromatography 215 99–108
N.J. Cartwright J.A. Buswell (1967) ArticleTitleThe separation of vanillate O-demethylase from protocatechuate 3,4-oxygenase by ultracentrifugation Biochemical Journal 105 767–770
N.J. Cartwright A.R.W. Smith (1967) ArticleTitleBacterial attack on phenolic ethers. An enzyme system demethylating vanillic acid Biochemical Journal 102 826–841
J.-P. Claverys B. Martin (2003) ArticleTitle2003 Bacterial ‘competence’ genes: signatures of active transformation or only remnants? Trends in Microbiology 11 161–165
M.I. Donnelly S. Dagley (1980) ArticleTitleProduction of methanol from aromatic acids by Pseudomonas putida Journal of Bacteriology 142 916–924
M. Droge A. Puhler W. Selbitschka (1998) ArticleTitleHorizontal gene transfer as a biosafety issue: A natural Phenomenon and public concern Journal of Biotechnology 64 75–90
J.M. Gonzalez F. Mayer M.A. Moran R.E. Hodson W.B. Whitman (1997) ArticleTitleMicrobulbifer hydrolyticus gen. nov.and Marinobacterium georgiensegen. nov., two marine bacteria from a lignin-rich pulp mill waste enrichment community International Journal of Systematic Bacteriology 47 369–376
El-Mansi, E.M.T. 1982 Methylhydroxylases in the bacterial metabolism of aromatic compounds. PhD thesis, University College of Wales (UCW), Aberystwyth, Wales, UK.
E.M.T. El-Mansi (1986) ArticleTitleSurvey of p-cresol assimilating bacteria: characterisation and identification of a p-cresol utilizing bacterium Journal of Applied Bacteriology 60 545–555
E.M.T. El-Mansi D.J. Hopper (1990) ArticleTitleResolution of the 4-hydroxy 3-methylbenzoate hydroxylase of Pseudomonas putida into two protein components FEMS Microbiology Letters 66 147–152
E.M.T El-Mansi H.G. Nimmo W.H. Holms (1985) ArticleTitleThe role of isocitrate in control of isocitrate dehydrogenase in E.coli. ML308 FEBS Letters 183 251–255
R.W. Horne (1965) ArticleTitleThe application of negative staining methods to quantitative electron microscopy Laboratory Investigation 14 1054–1068
D.J. Hopper (1976) ArticleTitleThe hydroxylation of p-cresol and its conversion to p-hydroxybenzaldehyde in Pseudomonas putida Biochemical and Biophysical Research Communications 69 462–468
Hopper, D.J. 1988 In Microbial Metabolism and the Carbon Cycle eds. Hagedorn, S.R., Hanson, R.S. & Kunz, D.A. pp. 247–258. Harwood Academic publishers. ISBN 3-71860472–8.
J. Kim J.H. Fuller G. Cecchini W.S. McIntire (1995) ArticleTitleCloning, sequencing and expression of the structural genes for the cytochrome and flavoprotein subunits of p-cresol methylhydroxylase from two strains of Pseudomonas putida Journal of Bacteriology 176 6349–6361
T.K. Kirk L.F. Lorenz (1973) ArticleTitleMethoxyhydroquinone, an intermediate of vanillate catabolism by Polyporus dichrous Applied Microbiology 26 173–175
T.K. Kirk E. Schultz W.J. Conners L.F. Lorenz J.G. Zeikus (1978) ArticleTitleInfluence of culture parameters on lignin metabolism by Phanerochaete chrysosporium Archives of Microbiology 117 277–285
P.R. Lehrbach I. McGregor J.M. Ward P. Broda (1983) ArticleTitleMolecular relationships between Pseudomonas INC P-9 degradative plasmids TOL, NAH and SAL Plasmid 10 164–174
A. Leonowicz J.-M. Bollag (1984) ArticleTitleFormation of 2-methoxy 1,4-benzoquinone from vanillic acid by fungal laccases at various pH values Experientia 40 544–545
S.V. Liu (1997) ArticleTitleAn improved colorimetric assay for vicinal diol determination by Ti (III) and its utilization for reporting microbial o-demethylation Journal of Microbiological Methods 29 85–95
M.G. Lorenz W. Wackernagel (1994) ArticleTitleBacterial gene transfer by natural genetic transformation in the environment Microbiology Reviews 58 563–602
I. Matic F. Taddie M. Radman (1996) ArticleTitleGenetic barriers among bacteria Trends in Microbiology 4 69–73
B. Morawski A. Segura L.N. Ornston (2000) ArticleTitleRepression of Acinetobacter vanillate demethylase synthesis by VanR, a member of the GntR family of transcriptional regulators FEMS Microbiology Letters 187 65–68
D. Naidu S.W. Ragsdale (2001) ArticleTitleCharacterization of a three-component vanillate O-demethylase fromMoorella thermoacetica Journal of Bacteriology 183 3276–3281
Y.A. Nikolaev N.S. Panikov S.M. Lukin G.A. Osipov (2001) ArticleTitleSaturated C21-CC33Hydrocarbons are involved in the self-regulation of Pseudomonas Fluorescens adhesion to a glass surface Microbiology 70 138–144
Picot, L., Abdelmoula, S.M., Merieau, A., Leroux, P., Cazin, L., Orange, N. & Feui, M.G.J. 2001 Microbes and Infection 3, 985–995.
D.W. Ribbons (1970) ArticleTitleStoichiometry of O-demethylase activity in Pseudomonas aeruginosa FEMS Microbiology Letters 8 101–104
L.F. Ross D.C. Chapital (1987) ArticleTitleSimultaneous determination of carbohydrates and products of carbohydrate metabolism in fermentation mixtures by HPLC Journal of Chromatography 25 112–117
C. Schäffer M. Graninger P. Messner (2001) ArticleTitleProkaryotic glycosylation Proteomics 1 248–261
C.M. Szymanski R. Yao C.P. Ewing T.J. Trust P. Guerry (1999) ArticleTitleEvidence for a system of general protein glycosylation in Campylobacter jejuni Molecular Microbiology 32 1022–1030
E.M. Top D. Springael N. Boon (2002) ArticleTitleCatabolic mobile genetic elements and their potential use in bioaugmentation of polluted soils and waters FEMS Microbiology Ecology 42 199–208
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El-mansi, E., Anderson, S. The hydroxylation of vanillate and its conversion to methoxyhydroquinone by a strain of Pseudomonas fluorescens devoid of demethylase and methylhydroxylase activities. World J Microbiol Biotechnol 20, 827–832 (2004). https://doi.org/10.1007/s11274-004-0871-y
- Hydroxylation, methylhydroxylase, oxidative decarboxylation, Pseudomonas fluorescens, vanillate metabolism