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. 1971 Mar;122(1):19–28. doi: 10.1042/bj1220019

Gentisic acid and its 3- and 4-methyl-substituted homologues as intermediates in the bacterial degradation of m-cresol, 3,5-xylenol and 2,5-xylenol

D J Hopper 1,*, P J Chapman 1
PMCID: PMC1176683  PMID: 4330964

Abstract

1. Intact cells of a non-fluorescent Pseudomonas grown with m-cresol, 2,5-xylenol, 3,5-xylenol, 3-ethyl-5-methylphenol or 2,3,5-trimethylphenol rapidly oxidized all these phenols to completion. 3-Hydroxybenzoate and 2,5-dihydroxybenzoate (gentisate) were also readily oxidized. 2. 3-Hydroxybenzoic acid and 2,5-dihydroxybenzoic acid were isolated as products of m-cresol oxidation by cells inhibited by αα′-bipyridyl. Alkyl-substituted 3-hydroxybenzoic acids and alkyl-substituted gentisic acids were formed similarly from 2,5-xylenol, 3,5-xylenol, 3-ethyl-5-methylphenol and 2,3,5-trimethylphenol. 3. When supplemented with NADH, not NADPH, extracts of cells grown with 2,5-xylenol catalysed the oxidation of all five phenols and accumulated the corresponding gentisic acids in the presence of αα′-bipyridyl. 4. Cells of a fluorescent Pseudomonas grown with m-cresol oxidized m-cresol, 3,5-xylenol and 3-ethyl-5-methylphenol to completion and oxidized 2,5-xylenol and 2,3,5-trimethylphenol partially. The oxidation product of 2,5-xylenol was identified as 3-hydroxy-4-methylbenzoic acid. In the presence of αα′-bipyridyl, 3-hydroxy-5-methylbenzoic acid and 3-methylgentisic acid were formed from 3,5-xylenol.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Bayly R. C., Dagley S., Gibson D. T. The metabolism of cresols by species of Pseudomonas. Biochem J. 1966 Nov;101(2):293–301. doi: 10.1042/bj1010293. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Chapman P. J., Hopper D. J. The bacterial metabolism of 2,4-xylenol. Biochem J. 1968 Dec;110(3):491–498. doi: 10.1042/bj1100491. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. DAGLEY S., PATEL M. D. Oxidation of p-cresol and related compounds by a Pseudomonas. Biochem J. 1957 Jun;66(2):227–233. doi: 10.1042/bj0660227. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Dagley S., Geary P. J., Wood J. M. The metabolism of protocatechuate by Pseudomonas testosteroni. Biochem J. 1968 Oct;109(4):559–568. doi: 10.1042/bj1090559. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Hopper D. J., Chapman P. J., Dagley S. The enzymic degradation of alkyl-substituted gentisates, maleates and malates. Biochem J. 1971 Mar;122(1):29–40. doi: 10.1042/bj1220029. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. INOUYE H. Uber die Bestandteile von Pirola japonica Sieb. V. Die Konstitution des Pirolatins. (3). Pharm Bull. 1954 Dec;2(4):359–367. doi: 10.1248/cpb1953.2.359. [DOI] [PubMed] [Google Scholar]
  7. LACK L. Enzymic cis-trans isomerization of maleylpyruvic acid. J Biol Chem. 1961 Nov;236:2835–2840. [PubMed] [Google Scholar]
  8. LACK L. The enzymic oxidation of gentisic acid. Biochim Biophys Acta. 1959 Jul;34:117–123. doi: 10.1016/0006-3002(59)90239-2. [DOI] [PubMed] [Google Scholar]
  9. LADD J. N. Oxidation of anthranilic acid by a species of Achromobacter isolated from soil. Nature. 1962 Jun 16;194:1099–1100. doi: 10.1038/1941099b0. [DOI] [PubMed] [Google Scholar]
  10. LOWRY O. H., ROSEBROUGH N. J., FARR A. L., RANDALL R. J. Protein measurement with the Folin phenol reagent. J Biol Chem. 1951 Nov;193(1):265–275. [PubMed] [Google Scholar]
  11. WALKER N., EVANS W. C. Pathways in the metabolism of the monohydroxybenzoic acids by soil bacteria. Biochem J. 1952 Dec;52(4):xxiii–xxiv. [PubMed] [Google Scholar]
  12. Wheelis M. L., Palleroni N. J., Stanier R. Y. The metabolism of aromatic acids by Pseudomonas testosteroni and P. acidovorans. Arch Mikrobiol. 1967;59(1):302–314. doi: 10.1007/BF00406344. [DOI] [PubMed] [Google Scholar]

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