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. 1995 Sep;61(9):3490–3493. doi: 10.1128/aem.61.9.3490-3493.1995

Transformation of Substituted Fluorenes and Fluorene Analogs by Pseudomonas sp. Strain F274

M Grifoll, S A Selifonov, P J Chapman
PMCID: PMC1388586  PMID: 16535132

Abstract

Pseudomonas sp. strain F274, previously shown to catabolize fluorene via fluorenone and its angular dioxygenation, 2(prm1),3(prm1)-dihydroxy-2-carboxybiphenyl, phthalate, and protocatechuate, was examined for its ability to transform substituted fluorenes and S- and N-heterocyclic analogs. Halogen- and methyl-substituted fluorenes were metabolized to correspondingly substituted phthalates via attack on the unsubstituted ring. In the case of 1-methylfluorene, initial oxidation of the methyl group to carboxyl prevented all other transformations but 9-monooxygenation. This strain also oxidized the S-heteroatoms and benzylic methylenic groups of fluorene analogs. No angular dioxygenation of S- and N-heterocycles was observed.

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Selected References

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  1. Boldrin B., Tiehm A., Fritzsche C. Degradation of phenanthrene, fluorene, fluoranthene, and pyrene by a Mycobacterium sp. Appl Environ Microbiol. 1993 Jun;59(6):1927–1930. doi: 10.1128/aem.59.6.1927-1930.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Bünz P. V., Cook A. M. Dibenzofuran 4,4a-dioxygenase from Sphingomonas sp. strain RW1: angular dioxygenation by a three-component enzyme system. J Bacteriol. 1993 Oct;175(20):6467–6475. doi: 10.1128/jb.175.20.6467-6475.1993. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Engesser K. H., Strubel V., Christoglou K., Fischer P., Rast H. G. Dioxygenolytic cleavage of aryl ether bonds: 1,10-dihydro-1,10-dihydroxyfluoren-9-one, a novel arene dihydrodiol as evidence for angular dioxygenation of dibenzofuran. FEMS Microbiol Lett. 1989 Nov;53(1-2):205–209. doi: 10.1016/0378-1097(89)90392-3. [DOI] [PubMed] [Google Scholar]
  4. Fortnagel P., Harms H., Wittich R. M., Krohn S., Meyer H., Sinnwell V., Wilkes H., Francke W. Metabolism of Dibenzofuran by Pseudomonas sp. Strain HH69 and the Mixed Culture HH27. Appl Environ Microbiol. 1990 Apr;56(4):1148–1156. doi: 10.1128/aem.56.4.1148-1156.1990. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Grifoll M., Casellas M., Bayona J. M., Solanas A. M. Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products. Appl Environ Microbiol. 1992 Sep;58(9):2910–2917. doi: 10.1128/aem.58.9.2910-2917.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Grifoll M., Selifonov S. A., Chapman P. J. Evidence for a novel pathway in the degradation of fluorene by Pseudomonas sp. strain F274. Appl Environ Microbiol. 1994 Jul;60(7):2438–2449. doi: 10.1128/aem.60.7.2438-2449.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Laborde A. L., Gibson D. T. Metabolism of dibenzothiophene by a Beijerinckia species. Appl Environ Microbiol. 1977 Dec;34(6):783–790. doi: 10.1128/aem.34.6.783-790.1977. [DOI] [PMC free article] [PubMed] [Google Scholar]
  8. Resnick S. M., Torok D. S., Gibson D. T. Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase. FEMS Microbiol Lett. 1993 Nov 1;113(3):297–302. doi: 10.1111/j.1574-6968.1993.tb06530.x. [DOI] [PubMed] [Google Scholar]
  9. Schocken M. J., Gibson D. T. Bacterial oxidation of the polycyclic aromatic hydrocarbons acenaphthene and acenaphthylene. Appl Environ Microbiol. 1984 Jul;48(1):10–16. doi: 10.1128/aem.48.1.10-16.1984. [DOI] [PMC free article] [PubMed] [Google Scholar]
  10. Selifonov S. A., Grifoll M., Gurst J. E., Chapman P. J. Isolation and characterization of (+)-1,1a-dihydroxy-1-hydrofluoren-9-one formed by angular dioxygenation in the bacterial catabolism of fluorene. Biochem Biophys Res Commun. 1993 May 28;193(1):67–76. doi: 10.1006/bbrc.1993.1591. [DOI] [PubMed] [Google Scholar]
  11. Trenz S. P., Engesser K. H., Fischer P., Knackmuss H. J. Degradation of fluorene by Brevibacterium sp. strain DPO 1361: a novel C-C bond cleavage mechanism via 1,10-dihydro-1,10-dihydroxyfluoren-9-one. J Bacteriol. 1994 Feb;176(3):789–795. doi: 10.1128/jb.176.3.789-795.1994. [DOI] [PMC free article] [PubMed] [Google Scholar]
  12. Wackett L. P., Kwart L. D., Gibson D. T. Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putida. Biochemistry. 1988 Feb 23;27(4):1360–1367. doi: 10.1021/bi00404a041. [DOI] [PubMed] [Google Scholar]
  13. Wittich R. M., Wilkes H., Sinnwell V., Francke W., Fortnagel P. Metabolism of dibenzo-p-dioxin by Sphingomonas sp. strain RW1. Appl Environ Microbiol. 1992 Mar;58(3):1005–1010. doi: 10.1128/aem.58.3.1005-1010.1992. [DOI] [PMC free article] [PubMed] [Google Scholar]

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