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Chemical Compound Review

Toluate     4-methylbenzoic acid

Synonyms: P-TOLUIC ACID, PubChem15433, CHEMBL21708, SureCN93638, NSC-2215, ...
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Disease relevance of p-Methylbenzoic acid

  • Transcription of the TOL plasmid toluate catabolic pathway operon of Pseudomonas putida is determined by a pair of co-ordinately and positively regulated overlapping promoters [1].
  • This hybrid encodes toluate oxygenase and all meta cleavage pathway enzymes, and it enables P. putida mt-2 and Escherichia coli K-12 cells to grow on m-toluate as sole carbon source [2].
  • The novel enzyme 4-methyl-2-enelactone methyl-isomerase was detected in, and purified to electrophoretic homogeneity from, p-toluate-grown cells of Rhodococcus rhodocrous N75, a nocardioform actinomycete [3].
  • Alcaligenes eutrophus wild-type strain 345 metabolizes m- and p-toluate via a catechol meta-cleavage pathway [4].
  • The cbdABC sequences show significant homology to benABC, which encode benzoate 1,2-dioxygenase from Acinetobacter calcoaceticus (52% identity at the deduced amino acid level), and to xylXYZ, which encode toluate 1,2-dioxygenase from Pseudomonas putida mt-2 (51% amino acid identity) [5].

High impact information on p-Methylbenzoic acid

  • In the xylT mutants, all the meta-cleavage enzymes were induced by p-toluate with the exception of catechol 2,3-dioxygenase whose activity was 1% of the p-toluate-induced activity in wild-type cells [6].
  • We further show that p-toluic acid and the bidentate transition state analogue, Kojic acid, displace chloride from the oxidized active site, whereas the monodentate substrate analogue, p-nitrophenol, forms a ternary complex with the enzyme and the chloride ion [7].
  • Using this approach, bilayer permeability coefficients of p-toluic acid and p-hydroxymethyl benzoic acid were determined to be 1.1 +/- 0.2 cm s-1 and (1.6 +/- 0.4) x 10(-3) cm s-1, respectively [8].
  • When a C23O gene (e.g., xylE) is introduced into this strain, the transformants cannot generally grow on p-toluate because 4-methylcatechol, a metabolite of p-toluate, is a substrate as well as a suicide inhibitor of C23O [9].
  • The ptsN gene of Pseudomonas putida encodes IIA(Ntr), a protein of the phosphoenol pyruvate:sugar phosphotransferase (PTS) system which is required for the C source inhibition of the sigma(54)-dependent promoter Pu of the TOL (toluate degradation) plasmid pWW0 [10].

Chemical compound and disease context of p-Methylbenzoic acid


Biological context of p-Methylbenzoic acid


Associations of p-Methylbenzoic acid with other chemical compounds


Gene context of p-Methylbenzoic acid

  • The electron transfer component of benzoate dioxygenase, encoded by benC, and the corresponding protein of the toluate 1,2-dioxygenase, encoded by xylZ, were each found to have an N-terminal region which resembled chloroplast-type ferredoxins and a C-terminal region which resembled several oxidoreductases [21].
  • No activities of the TOL plasmid encoded toluate dioxygenase and catechol 2,3-dioxygenase were detectable in strain CG220 [22].
  • DNA fragments containing the xylD and xylL genes of TOL plasmid pWW0 -161 of Pseudomonas putida, which code for the catabolic enzymes toluate 1,2-dioxygenase and dihydrodihydroxybenzoic acid dehydrogenase, respectively, and the nahG gene of the NAH plasmid NAH7 , which codes for salicylate hydroxylase, were cloned in pBR322 vector plasmid [23].
  • Southern hybridizations demonstrated that DNA encoding the benzoate dioxygenase structural genes showed homology to DNA encoding toluate dioxygenase from the TOL plasmid pWW0, but benR did not show homology to xylS [24].
  • Nonlinear regression analyses of flux-pH profiles using a model which accounts for unstirred layer effects yielded membrane permeability coefficients (PRX) that varied from 1.1 cm/s for p-toluic acid to 4.1 x 10(-5) cm/s for the alpha-carbamoyl-p-toluic acid [19].


  1. Transcription of the TOL plasmid toluate catabolic pathway operon of Pseudomonas putida is determined by a pair of co-ordinately and positively regulated overlapping promoters. Mermod, N., Lehrbach, P.R., Reineke, W., Timmis, K.N. EMBO J. (1984) [Pubmed]
  2. Molecular and functional analysis of the TOL plasmid pWWO from Pseudomonas putida and cloning of genes for the entire regulated aromatic ring meta cleavage pathway. Franklin, F.C., Bagdasarian, M., Bagdasarian, M.M., Timmis, K.N. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  3. Purification and characterization of 4-methylmuconolactone methyl-isomerase, a novel enzyme of the modified 3-oxoadipate pathway in nocardioform actinomycetes. Bruce, N.C., Cain, R.B., Pieper, D.H., Engesser, K.H. Biochem. J. (1989) [Pubmed]
  4. Characterization of a TOL-like plasmid from Alcaligenes eutrophus that controls expression of a chromosomally encoded p-cresol pathway. Hughes, E.J., Bayly, R.C., Skurray, R.A. J. Bacteriol. (1984) [Pubmed]
  5. Cloning, nucleotide sequence, and expression of the plasmid-encoded genes for the two-component 2-halobenzoate 1,2-dioxygenase from Pseudomonas cepacia 2CBS. Haak, B., Fetzner, S., Lingens, F. J. Bacteriol. (1995) [Pubmed]
  6. In vivo reactivation of catechol 2,3-dioxygenase mediated by a chloroplast-type ferredoxin: a bacterial strategy to expand the substrate specificity of aromatic degradative pathways. Polissi, A., Harayama, S. EMBO J. (1993) [Pubmed]
  7. Structural basis and mechanism of the inhibition of the type-3 copper protein tyrosinase from Streptomyces antibioticus by halide ions. Tepper, A.W., Bubacco, L., Canters, G.W. J. Biol. Chem. (2002) [Pubmed]
  8. Transport methods for probing the barrier domain of lipid bilayer membranes. Xiang, T.X., Chen, X., Anderson, B.D. Biophys. J. (1992) [Pubmed]
  9. Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol. Okuta, A., Ohnishi, K., Harayama, S. Appl. Environ. Microbiol. (2004) [Pubmed]
  10. Evidence of multiple regulatory functions for the PtsN (IIA(Ntr)) protein of Pseudomonas putida. Cases, I., Lopez, J.A., Albar, J.P., De Lorenzo, V. J. Bacteriol. (2001) [Pubmed]
  11. Comparative biochemical and genetic analysis of naphthalene degradation among Pseudomonas stutzeri strains. Rosselló-Mora, R.A., Lalucat, J., García-Valdés, E. Appl. Environ. Microbiol. (1994) [Pubmed]
  12. Genetic analysis of a relaxed substrate specificity aromatic ring dioxygenase, toluate 1,2-dioxygenase, encoded by TOL plasmid pWW0 of Pseudomonas putida. Harayama, S., Rekik, M., Timmis, K.N. Mol. Gen. Genet. (1986) [Pubmed]
  13. Chemical structure and biodegradability of halogenate aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Reineke, W., Knackmuss, H.J. Biochim. Biophys. Acta (1978) [Pubmed]
  14. Physical and functional mapping of RP4-TOL plasmid recombinants: analysis of insertion and deletion mutants. Nakazawa, T., Inouye, S., Nakazawa, A. J. Bacteriol. (1980) [Pubmed]
  15. The organization of the Pm promoter of the TOL plasmid reflects the structure of its cognate activator protein XylS. Kessler, B., Timmis, K.N., de Lorenzo, V. Mol. Gen. Genet. (1994) [Pubmed]
  16. Biotransformation of p-toluic acid in anoxic estuarine sediments under a CO2 or N2/H2 atmosphere. Kuo, C.E., Chi, W.C., Liu, S.M. Chemosphere (2001) [Pubmed]
  17. Molecular cloning of gene xylS of the TOL plasmid: evidence for positive regulation of the xylDEGF operon by xylS. Inouye, S., Nakazawa, A., Nakazawa, T. J. Bacteriol. (1981) [Pubmed]
  18. Adenosylcobalamin-mediated methyl transfer by toluate cis-dihydrodiol dehydrogenase of the TOL plasmid pWW0. Lee, J.Y., Park, H.S., Kim, H.S. J. Bacteriol. (1999) [Pubmed]
  19. Substituent contributions to the transport of substituted p-toluic acids across lipid bilayer membranes. Xiang, T.X., Anderson, B.D. Journal of pharmaceutical sciences. (1994) [Pubmed]
  20. Pure bacterial isolates that convert p-xylene to terephthalic acid. Bramucci, M.G., McCutchen, C.M., Singh, M., Thomas, S.M., Larsen, B.S., Buckholz, J., Nagarajan, V. Appl. Microbiol. Biotechnol. (2002) [Pubmed]
  21. Nucleotide sequences of the Acinetobacter calcoaceticus benABC genes for benzoate 1,2-dioxygenase reveal evolutionary relationships among multicomponent oxygenases. Neidle, E.L., Hartnett, C., Ornston, L.N., Bairoch, A., Rekik, M., Harayama, S. J. Bacteriol. (1991) [Pubmed]
  22. Loss of the TOL meta-cleavage pathway functions of Pseudomonas putida strain PaW1 (pWW0) during growth on toluene. Brinkmann, U., Ramos, J.L., Reineke, W. J. Basic Microbiol. (1994) [Pubmed]
  23. Enzyme recruitment in vitro: use of cloned genes to extend the range of haloaromatics degraded by Pseudomonas sp. strain B13. Lehrbach, P.R., Zeyer, J., Reineke, W., Knackmuss, H.J., Timmis, K.N. J. Bacteriol. (1984) [Pubmed]
  24. Characterization of Pseudomonas putida mutants unable to catabolize benzoate: cloning and characterization of Pseudomonas genes involved in benzoate catabolism and isolation of a chromosomal DNA fragment able to substitute for xylS in activation of the TOL lower-pathway promoter. Jeffrey, W.H., Cuskey, S.M., Chapman, P.J., Resnick, S., Olsen, R.H. J. Bacteriol. (1992) [Pubmed]
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