1887

Abstract

Summary: A bacterium capable of growth on 4-hydroxyacetophenone was isolated from soil and identified as an sp. Intact cells rapidly oxidized (4-hydroxybenzoyl)methanol, 4-hydroxybenzoate and protocatechuate as well as the growth substrate, and also converted the substrate analogue (4-methoxybenzoyl)methanol to 4-methoxybenzoic acid. When provided with NADH, cell-free extracts oxidized 4-hydroxyacetophenone to 4-hydroxybenzoate and formate, the same products as were formed from (4-hydroxybenzoyl)methanol without NADH. The oxidation of 4-hydroxybenzoate by cell-free extracts required NADPH and the product from both this and protocatechuate oxidation was 3-oxoadipate. A pathway for the catabolism of 4-hydroxyacetophenone, by hydroxylation to (4-hydroxybenzoyl)methanol followed by oxidative cleavage to 4-hydroxybenzoate and formate and hydroxylation of the 4-hydroxybenzoate to protocatechuate, is proposed. Oxidation of protocatechuate was by the pathway. The key enzymes in the proposed pathway were induced by growth on 4-hydroxyacetophenone.

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1985-07-01
2024-04-26
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References

  1. Cripps R. E. 1975; The microbial metabolism of acetophenone and some chloroacetophenones by an Arthrobacter species. Biochemical Journal 152:233–241
    [Google Scholar]
  2. Cripps R. E., Trudgill P. W., Whateley J. G. 1978; The metabolism of 1-phenylethanol and acetophenone by Nocardia T5 and an Arthrobacter species. European Journal of Biochemistry 86:175–186
    [Google Scholar]
  3. Forney F. W., Markovetz A. J. 1969; An enzyme system for aliphatic methyl ketone oxidation. Biochemical and Biophysical Research Communications 37:31–38
    [Google Scholar]
  4. Glenn J. K., Morgan M. A., Mayfield M. B., Kuwahara M., Gold M. H. 1983; An extracellular H2O2-requiring enzyme preparation involved in lignin biodegradation by the white rot basidiomycete Phanerochaete chrysosporium . Biochemical and Biophysical Research Communications 114:1077–1083
    [Google Scholar]
  5. Gunter S. E. 1953; The enzymatic oxidation of p-hydroxymandelic acid to p-hydroxybenzoic acid. Journal of Bacteriology 66:341–346
    [Google Scholar]
  6. Holding A. J., Shewan J. M. 1974; The genus Alcaligenes . In Bergey’s Manual of Determinative Bacteriology 8th edn, pp 273–275 Edited by Buchanan R. E., Gibbons N. E. Baltimore: Williams & Wilkins;
    [Google Scholar]
  7. Hopper D. J., Elmorsi E. A. 1984; Cleavage of formate from ω,4-dihydroxyacetophenone. An unusual oxygen-requiring reaction in the bacterial catabolism of 4-hydroxycetophenone. Biochemical Journal 218:269–272
    [Google Scholar]
  8. Kennedy S. I. T., Fewson C. A. 1968; Enzymes of the mandelate pathway in bacterium NCIB 8250. Biochemical Journal 107:497–506
    [Google Scholar]
  9. Klamann E., Lingens F. 1980; Degradation of (−)-ephedrine by Pseudomonas putida. Detection of (−)-ephedrine: NAD+-oxidoreductase from Arthrobacter globiformis . Zeitschrift für Naturforschung 35c:80–87
    [Google Scholar]
  10. Kotera U., Koulima T., Minoda Y., Yamada K. 1972; Isolation and chemical structure of new oxidation product of 5-ketogluconic acid and a hypothetical pathway from glucose to tartaric acid through this new compound. Agricultural and Biological Chemistry 36:1315–1325
    [Google Scholar]
  11. Lorimer G. H. 1981; The carboxylation and oxygenation of ribulose 1,5-bisphosphate: the primary events in photosynthesis and photorespiration. Annual Review of Plant Physiology 32:349–383
    [Google Scholar]
  12. McIntire W., Hopper D. J., Craig J. C., Everhart E. T., Webster R. V., Causer M. J., Singer T. P. 1984; Stereochemistry of l-(4ʹ-hydroxyphenyl)ethanol produced by hydroxylation of 4-ethylphenol by p-cresol methylhydroxylase. Biochemical Journal 224:617–621
    [Google Scholar]
  13. Minamikawa T., Jayasankar N. P., Bohn B. A., Taylor I. E. P., Towers G. H. N. 1970; An inducible hydrolase from Aspergillus niger, acting on carbon-carbon bonds, for phlorrhizin and other C-acylated phenols. Biochemical Journal 116:889–897
    [Google Scholar]
  14. Norris D. B., Trudgill P. W. 1971; The metabolism of cyclohexanol by Nocardia globerula CLI. Biochemical Journal 121:363–370
    [Google Scholar]
  15. Ornston L. N., Stanier R. Y. 1966; The conversion of catechol and protocatechuate to β-ketoadipate by Pseudomonas putida . Journal of Biological Chemistry 131:42–48
    [Google Scholar]
  16. Rahim M. A., Sih C. J. 1966; Mechanisms of steroid oxidation by microorganisms. XI. Enzymatic cleavage of the pregnane side chain. Journal of Biological Chemistry 241:3615–3623
    [Google Scholar]
  17. Robertson A., Robinson R. 1928; Experiments on the synthesis of anthrocyanins. Journal of the Chemical Society1460–1472
    [Google Scholar]
  18. Ronkainen P. 1963; Die Dunnschichtchromato graphie der Ketosauren. Journal of Chromatography 11:228–237
    [Google Scholar]
  19. Rosenberger R. F., Elsden S. R. 1960; The yields of Streptococcus faecalis grown in continuous culture. Journal of General Microbiology 22:726–739
    [Google Scholar]
  20. Rothera A. C. H. 1908; Note on the sodium nitroprusside reaction for acetone. Journal of Physiology 37:491–494
    [Google Scholar]
  21. Whateley J. G. 1978 The microbial metabolism of 1 phenylethanol and acetophenone PhD thesis University College of Wales, Aberystwyth;
    [Google Scholar]
  22. Vogel A. I. 1956 Practical Organic Chemistry 3rd edn London: Longman, Green;
    [Google Scholar]
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