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The formation of phenol in the degradation ofp-hydroxybenzoic acid byKlebsiella aerogenes (Aerobacter aerogenes)

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Abstract

After growth ofK. aerogenes in chemically defined media consisting of mineral salts andp-hydroxybenzoate with or without glucose, phenol was found in the culture fluid at concentrations inhibiting further growth. Bacteria adapted to mineral salts medium containingp-hydroxybenzoate as sole source of carbon and energy produced small but isolable quantities of 3,4-dihydroxybenzoic acid and catechol and oxidized these substances as rapidly asp-hydroxybenzoate. Bacteria adapted to mineral salts medium containing glucose as sole carbon and energy source did not oxidizep-hydroxybenzoate, 3,4-dihydroxybenzoate or catechol. Bacteria adapted to glucose medium or top-hydroxybenzoate medium did not oxidize or utilize phenol as sole carbon and energy source. A metabolic pathway forp-hydroxybenzoate degradation is proposed and the formation of phenol is attributed to a side reaction.

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References

  • Beveridge, E. G. andHugo, W. B. 1964. The metabolism of gallic acid byPseudomonas convexa X. I. - J. Appl. Bacteriol.27: 448–460.

    Google Scholar 

  • Dagley, S. 1967. The microbial metabolism of phenolics, p. 287–313.In A. D. McLaren and G. H. Peterson, [eds.], Soil biochemistry. - Edward Arnold, London.

    Google Scholar 

  • Evans, W. C. 1947. Oxidation of phenol and benzoic acid by some soil bacteria. - Biochem. J.41: 373–382.

    Google Scholar 

  • Gibson, D. T., Wood, J. M., Chapman, P. J. andDagley, S. 1967. Bacterial degradation of aromatic compounds. - Biotech. Bioengin.9: 33–44.

    Google Scholar 

  • Grant, D. J. W. 1967. Kinetic aspects of the growth ofKlebsiella aerogenes with some benzenoid carbon sources. - J. Gen. Microbiol.46: 213–224.

    Google Scholar 

  • Hinshelwood, C. N. 1946. The chemical kinetics of the bacterial cell. - Clarendon Press, Oxford.

    Google Scholar 

  • Kakihara, Y. andIchihara, K. 1953. Studies of phenol formation. I. Method of the determination of phenol and its microbial formation from tyrosine and tyrosine derivatives. - Med. J. Osaka Univ.3: 497–507.

    Google Scholar 

  • Openshaw, H. T. 1955. Laboratory manual of qualitative organic analysis, 3rd ed. - University Press, Cambridge.

    Google Scholar 

  • Pastuska, G. 1961. p. 177in K. Randerath. 1963. Thin layer chromatography. - Academic Press, New York and London. - Z. Analyt. Chem.179: 355.

    Google Scholar 

  • Pastuska, G. andPetrowitz, H. J. 1962. p. 177in K. Randerath. 1963. Thin layer chromatography. -Academic Press, New York and London. - Chemiker Ztg.86: 311.

    Google Scholar 

  • Pittard, A. J., Gibson, F. andDoy, C. H. 1961. Phenolic compounds accumulated by washed cell suspensions of a tryptophan auxotroph ofAerobacter aerogenes. - Biochim. Biophys. Acta49: 485–494.

    Google Scholar 

  • Pittard, A. J., Gibson, F. andDoy, C. H. 1962. A possible relationship between the formation ofo-dihydric phenols and tryptophan biosynthesis byAerobacter aerogenes. - Biochim. Biophys. Acta57: 290–298.

    Google Scholar 

  • Poole, E. A. andHinshelwood, C. N. 1940. Physico-chemical aspects of bacterial growth. VI. The influence of toxic substances on growth rate, stationary population, and fermentation reactions ofBact. lactis aerogenes. VII. Influence of phenol on the death rate ofBact. lactis aerogenes. - J. Chem. Soc.1940: 1565–1574.

    Google Scholar 

  • Proctor, M. H. andScher, S. 1960. Decomposition of benzoate by a photosynthetic bacterium. - Biochem. J.76: 33 P.

    Google Scholar 

  • Randerath, K. 1963. Thin-layer chromatography.- Academic Press, New York and London.

    Google Scholar 

  • Ratledge, C. 1967. The production of anN-acylanthranilic acid from shikimic acid and the effect of iron deficiency on the biosynthesis of other aromatic compounds byAerobacter aerogenes. - Biochim. Biophys. Acta141: 55–63.

    Google Scholar 

  • Rhein, M. 1918. Über den Abbau des Tyrosins durchBact. coli phenologenes nebst einer Notiz über die Zusammensetzung der Harnphenole des Menschen. - Biochem. Z.87: 123–128.

    Google Scholar 

  • Ribbons, D. W. 1965. The microbiological degradation of aromatic compounds. - Ann. Rep. Progr. Chem.62: 445–468.

    Google Scholar 

  • Stahl, E. 1962. Thin-layer chromatography, a laboratory handbook. - Springer Verlag, Berlin.

    Google Scholar 

  • Stanier, R. Y. 1947. Simultaneous adaptation: a new technique for the study of metabolic pathways. - J. Bacteriol.54: 339–348.

    Google Scholar 

  • Stanier, R. Y. 1950. Problems of bacterial oxidative metabolism. - Bacteriol. Rev.14: 179–191.

    Google Scholar 

  • Stanier, R. Y., Sleeper, B. P., Tsuchida, M. andMacdonald, D. L. 1950. The bacterial oxidation of aromatic compounds. III. The enzymatic oxidation of catechol and protocatechuic acid toβ-ketoadipic acid. - J. Bacteriol.59: 137–151.

    Google Scholar 

  • Uchida, M., Taketomo, Y., Kakihara, Y. andIchihara, K. 1953. Studies of phenol formation. II.β-Tyrosinase and the role of pyridoxal in phenol formation. - Med. J. Osaka Univ.3: 509–519.

    Google Scholar 

  • Umbreit, W. W., Burris, R. M. andStauffer, J. F. 1964. Manometric techniques, 4th ed. - Burgess Publishing Co., Minneapolis, Minnesota.

    Google Scholar 

  • Updegraff, D. M. 1949. The production of phenol and para-cresol by marine bacteria. - J. Bacteriol.57: 555–564.

    Google Scholar 

  • Williams, O. B. andEnglish, J. D. 1950. Phenol production by coliform bacteria. - J. Bacteriol.60: 101–102.

    Google Scholar 

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Patel, J.C., Grant, D.J.W. The formation of phenol in the degradation ofp-hydroxybenzoic acid byKlebsiella aerogenes (Aerobacter aerogenes) . Antonie van Leeuwenhoek 35, 53–64 (1969). https://doi.org/10.1007/BF02219116

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