MetaCyc Pathway: fluorene degradation I
Inferred from experiment

Pathway diagram: fluorene degradation I

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: fluorene degradation via 9-fluorenone

Superclasses: Degradation/Utilization/AssimilationAromatic Compounds DegradationFluorene Degradation

Some taxa known to possess this pathway include : Brevibacterium sp. DPO 1361

Expected Taxonomic Range: Actinobacteria

fluorene, a 3-ring polycyclic aromatic hydrocarbon (PAH), is a constituent of fossil fuels and is a product of incomplete combustion. It is also an EPA priority pollutant.

Several bacteria, including Brevibacterium sp. DPO 1361 [Trenz94], Arthrobacter sp. F101 [Casellas97, Grifoll92], and Staphylococcus auricularis DBF63 [Monna93] are able to utilize fluorene as a sole source of carbon and energy. Pseudomonas sp. NCIB9816-4, on the other hand, cannot grow with fluorene as a sole source of carbon and energy, but can transform fluorene to 9-fluorenol by the reduced substrate specificity of its naphthalene dioxygenase [Resnick96].

Three pathways were proposed for fluorene degradation by Arthrobacter sp. F101, two of which are believed to be productive routes that lead to central metabolism while the third is believed to be a non-productive route that leads to dead-end products [Casellas97, Grifoll92]. A similar non-productive pathway for fluorene transformation was proposed for Staphylococcus auricularis DBF63 [Monna93]. Since Staphylococcus auricularis DBF63 is able to grow on fluorene as the sole source of carbon and energy a productive route must exist as well; however, it has yet to be elucidated.

Brevibacterium sp. DPO 1361 [Trenz94] is postulated to degrade fluorene via 9-fluorenol and 9-fluorenone, the initial two products in the proposed non-productive routes of fluorene transformation in Arthrobacter sp. F101 [Casellas97, Grifoll92] and Staphylococcus auricularis DBF63 [Monna93]. No 9-fluorenol monoxygenase activity was detected in crude cell extracts of Brevibacterium sp. DPO 1361, so it was postulated that the transformation is probably due to monooxygenation by a dioxygenase type system, such as naphthalene dioxygenase [Trenz94]. 9-Fluorenol is postulated to be transformed to 9-fluorenone by a dehydrogenase, which is induced during growth on fluorene, but not on dibenzofuran [Trenz94]. The subsequent product, 9-fluorenone, is postulated to undergo angular dioxygenation to 1,10-dihydro-1,10-dihydroxyfluoren-9-one (DDF) [Trenz94]. The metabolites, 9-fluorenol, 9-fluorenone, 1,10-dihydro-1,10-dihydroxyfluoren-9-one and phthalate were detected in assays of dibenzofuran-grown cells of Brevibacterium sp. DPO 1361 [Engesser89].

Variants: fluorene degradation II

Created 11-Nov-1998 by Krieger CJ, SRI International
Revised 29-Jul-2009 by Caspi R, SRI International


Casellas97: Casellas M, Grifoll M, Bayona JM, Solanas AM (1997). "New metabolites in the degradation of fluorene by Arthrobacter sp. strain F101." Appl Environ Microbiol 63(3);819-26. PMID: 9055403

Engesser89: Engesser KH, Strubel V, Christoglou K, Fischer P, Rast HG (1989). "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 53(1-2);205-9. PMID: 2612886

Grifoll92: Grifoll M, Casellas M, Bayona JM, Solanas AM (1992). "Isolation and characterization of a fluorene-degrading bacterium: identification of ring oxidation and ring fission products." Appl Environ Microbiol 58(9);2910-7. PMID: 1444405

Monna93: Monna L, Omori T, Kodama T (1993). "Microbial degradation of dibenzofuran, fluorene, and dibenzo-p-dioxin by Staphylococcus auriculans DBF63." Appl Environ Microbiol 59(1);285-9. PMID: 8439154

Resnick96: Resnick SM, Gibson DT (1996). "Regio- and stereospecific oxidation of fluorene, dibenzofuran, and dibenzothiophene by naphthalene dioxygenase from Pseudomonas sp. strain NCIB 9816-4." Appl Environ Microbiol 62(11);4073-80. PMID: 8899998

Trenz94: Trenz SP, Engesser KH, Fischer P, Knackmuss HJ (1994). "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 176(3);789-95. PMID: 8300532

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Ensley82: Ensley BD, Gibson DT, Laborde AL (1982). "Oxidation of naphthalene by a multicomponent enzyme system from Pseudomonas sp. strain NCIB 9816." J Bacteriol 149(3);948-54. PMID: 7037744

Ensley83: Ensley BD, Gibson DT (1983). "Naphthalene dioxygenase: purification and properties of a terminal oxygenase component." J Bacteriol 155(2);505-11. PMID: 6874638

He99: He Z, Spain JC (1999). "Comparison of the downstream pathways for degradation of nitrobenzene by Pseudomonas pseudoalcaligenes JS45 (2-aminophenol pathway) and by Comamonas sp. JS765 (catechol pathway)." Arch Microbiol 171(5);309-16. PMID: 10382261

Johnson04: Johnson WH, Wang SC, Stanley TM, Czerwinski RM, Almrud JJ, Poelarends GJ, Murzin AG, Whitman CP (2004). "4-Oxalocrotonate tautomerase, its homologue YwhB, and active vinylpyruvate hydratase: synthesis and evaluation of 2-fluoro substrate analogues." Biochemistry 43(32);10490-501. PMID: 15301547

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Simon93: Simon MJ, Osslund TD, Saunders R, Ensley BD, Suggs S, Harcourt A, Suen WC, Cruden DL, Gibson DT, Zylstra GJ (1993). "Sequences of genes encoding naphthalene dioxygenase in Pseudomonas putida strains G7 and NCIB 9816-4." Gene 127(1);31-7. PMID: 8486285

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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