Skip to main content
PMC home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1985 Sep;163(3):1126–1135. doi: 10.1128/jb.163.3.1126-1135.1985

beta-Ketoadipate pathway in Trichosporon cutaneum modified for methyl-substituted metabolites.

J B Powlowski, S Dagley
PMCID: PMC219248  PMID: 4040904

Abstract

Trichosporon cutaneum, when grown with p-cresol, catalyzed intradiol fission of the benzene nucleus of 4-methylcatechol before the complete catabolism of these two substrates. Steps in their conversion to pyruvate and acetyl coenzyme A were investigated by using cell extracts, and some properties of various new microbial catabolites are also described. These included (-)-2,5-dihydro-3-methyl-5-oxofuran-2-acetic acid (beta-methylmuconolactone) and (-)-3-keto-4-methyladipic acid and its coenzyme A ester; the latter was degraded by an enzymatic reaction sequence that included the coenzyme A esters of methylsuccinic, itaconic, and citramalic acids. A notable feature of this sequence is the formation of beta-methylmuconolactone which can be readily metabolized, in contrast to the analogous reaction in bacteria that gives the "dead-end" compound gamma-methylmuconolactone; this compound cannot be enzymatically degraded and so renders the beta-ketoadipate pathway unavailable for methyl-substituted bacterial sources of carbon that are catabolized by way of 4-methylcatechol.

Full text

PDF
1126

Selected References

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

  1. ADLER J., WANG S. F., LARDY H. A. The metabolism of itaconic acid by liver mitochondria. J Biol Chem. 1957 Dec;229(2):865–879. [PubMed] [Google Scholar]
  2. ALLRED J. B. INTERFERENCE BY THIOLS IN ACETOACETATE DETERMINATION. Anal Biochem. 1965 Apr;11:138–143. doi: 10.1016/0003-2697(65)90053-9. [DOI] [PubMed] [Google Scholar]
  3. Anderson J. J., Dagley S. Catabolism of aromatic acids in Trichosporon cutaneum. J Bacteriol. 1980 Feb;141(2):534–543. doi: 10.1128/jb.141.2.534-543.1980. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Anderson J. J., Dagley S. Catabolism of tryptophan, anthranilate, and 2,3-dihydroxybenzoate in Trichosporon cutaneum. J Bacteriol. 1981 Apr;146(1):291–297. doi: 10.1128/jb.146.1.291-297.1981. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. BUSCH H., HURLBERT R. B., POTTER V. R. Anion exchange chromatography of acids of the citric acid cycle. J Biol Chem. 1952 May;196(2):717–727. [PubMed] [Google Scholar]
  6. 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]
  7. CHANTRENNE H., LIPMANN F. Coenzyme A dependence and acetyl donor function of the pyruvate-formate exchange system. J Biol Chem. 1950 Dec;187(2):757–767. [PubMed] [Google Scholar]
  8. Catelani D., Fiecchi A., Galli E. Dextro-gamma-carboxymethyl-gamma-methyl-delta-alpha-butenolide. A 1,2-ring-fission product of 4-methylcatechol by Pseudomonas desmolyticum. Biochem J. 1971 Jan;121(1):89–92. doi: 10.1042/bj1210089. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Cooper R. A., Kornberg H. L. The utilization of itaconate by Pseudomonas sp. Biochem J. 1964 Apr;91(1):82–91. doi: 10.1042/bj0910082. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Corkey B. E., Brandt M., Williams R. J., Williamson J. R. Assay of short-chain acyl coenzyme A intermediates in tissue extracts by high-pressure liquid chromatography. Anal Biochem. 1981 Nov 15;118(1):30–41. doi: 10.1016/0003-2697(81)90152-4. [DOI] [PubMed] [Google Scholar]
  11. 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]
  12. 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]
  13. Dorn E., Knackmuss H. J. Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of catechol. Biochem J. 1978 Jul 15;174(1):85–94. doi: 10.1042/bj1740085. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Hareland W. A., Crawford R. L., Chapman P. J., Dagley S. Metabolic function and properties of 4-hydroxyphenylacetic acid 1-hydroxylase from Pseudomonas acidovorans. J Bacteriol. 1975 Jan;121(1):272–285. doi: 10.1128/jb.121.1.272-285.1975. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. 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]
  16. KATAGIRI M., HAYAISHI O. Enzymatic degradation of beta-ketoadipic acid. J Biol Chem. 1957 May;226(1):439–448. [PubMed] [Google Scholar]
  17. Keat M. J., Hopper D. J. P-cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9896. Biochem J. 1978 Nov 1;175(2):649–658. doi: 10.1042/bj1750649. [DOI] [PMC free article] [PubMed] [Google Scholar]
  18. Kojima Y., Fujisawa H., Nakazawa A., Nakazawa T., Kanetsuna F., Taniuchi H., Nozaki M., Hayaishi O. Studies on pyrocatechase. I. Purification and spectral properties. J Biol Chem. 1967 Jul 25;242(14):3270–3278. [PubMed] [Google Scholar]
  19. Massey L. K., Sokatch J. R., Conrad R. S. Branched-chain amino acid catabolism in bacteria. Bacteriol Rev. 1976 Mar;40(1):42–54. doi: 10.1128/br.40.1.42-54.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. NAKAGAWA H., INOUE H., TAKEDA Y. CHARACTERISTICS OF CATECHOL OXYGENASE FROM BREVIBACTERIUM FUSCUM. J Biochem. 1963 Jul;54:65–74. doi: 10.1093/oxfordjournals.jbchem.a127748. [DOI] [PubMed] [Google Scholar]
  21. Neujahr H. Y., Varga J. M. Degradation of phenols by intact cells and cell-free preparations of Trichosporon cutaneum. Eur J Biochem. 1970 Mar 1;13(1):37–44. doi: 10.1111/j.1432-1033.1970.tb00896.x. [DOI] [PubMed] [Google Scholar]
  22. OTTEY L., TATUM E. L. The cleavage of beta-ketoadipic acie by Neurospora crassa. J Biol Chem. 1957 Nov;229(1):77–83. [PubMed] [Google Scholar]
  23. Ornston L. N., Stanier R. Y. The conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. J Biol Chem. 1966 Aug 25;241(16):3776–3786. [PubMed] [Google Scholar]
  24. Patel R. N., Hou C. T., Felix A., Lillard M. O. Catechol 1,2-dioxygenase from Acinetobacter calcoaceticus: purification and properties. J Bacteriol. 1976 Jul;127(1):536–544. doi: 10.1128/jb.127.1.536-544.1976. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. Powlowski J. B., Ingebrand J., Dagley S. Enzymology of the beta-ketoadipate pathway in Trichosporon cutaneum. J Bacteriol. 1985 Sep;163(3):1136–1141. doi: 10.1128/jb.163.3.1136-1141.1985. [DOI] [PMC free article] [PubMed] [Google Scholar]
  26. SISTROM W. R., STANIER R. Y. The mechanism of formation of beta-ketoadipic acid by bacteria. J Biol Chem. 1954 Oct;210(2):821–836. [PubMed] [Google Scholar]
  27. STANIER R. Y., SLEEPER B. P., TSUCHIDA M., MACDONALD D. L. The bacterial oxidation of aromatic compounds; III. The enzymatic oxidation of catechol and protocatechuic acid to beta-ketoadipic acid. J Bacteriol. 1950 Feb;59(2):137–151. doi: 10.1128/jb.59.2.137-151.1950. [DOI] [PMC free article] [PubMed] [Google Scholar]
  28. Sparnins V. L., Burbee D. G., Dagley S. Catabolism of L-tyrosine in Trichosporon cutaneum. J Bacteriol. 1979 May;138(2):425–430. doi: 10.1128/jb.138.2.425-430.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
  29. Spoelstra S. F. Degradation of tyrosine in anaerobically stored piggery wastes and in pig feces. Appl Environ Microbiol. 1978 Nov;36(5):631–638. doi: 10.1128/aem.36.5.631-638.1978. [DOI] [PMC free article] [PubMed] [Google Scholar]
  30. Stanier R. Y., Ornston L. N. The beta-ketoadipate pathway. Adv Microb Physiol. 1973;9(0):89–151. [PubMed] [Google Scholar]
  31. Stanier R. Y., Palleroni N. J., Doudoroff M. The aerobic pseudomonads: a taxonomic study. J Gen Microbiol. 1966 May;43(2):159–271. doi: 10.1099/00221287-43-2-159. [DOI] [PubMed] [Google Scholar]
  32. Varga J. M., Neujahr H. Y. Purification and properties of catechol 1,2-oxygenase from Trichosporon cutaneum. Eur J Biochem. 1970 Feb;12(3):427–434. doi: 10.1111/j.1432-1033.1970.tb00869.x. [DOI] [PubMed] [Google Scholar]
  33. WALKER P. G. A colorimetric method for the estimation of acetoacetate. Biochem J. 1954 Dec;58(4):699–704. doi: 10.1042/bj0580699. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES