2005
DOI: 10.1021/bi047724y
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Chemistry of the Catalytic Conversion of Phthalate into Its cis-Dihydrodiol during the Reaction of Oxygen with the Reduced Form of Phthalate Dioxygenase

Abstract: The phthalate dioxygenase system, a Rieske non-heme iron dioxygenase, catalyzes the dihydroxylation of phthalate to form the 4,5-dihydro-cis-dihydrodiol of phthalate (DHD). It has two components: phthalate dioxygenase (PDO), a multimer with one Rieske-type [2Fe-2S] and one mononuclear Fe(II) center per monomer, and a reductase (PDR) that contains flavin mononucleotide (FMN) and a plant-type ferredoxin [2Fe-2S] center. This work shows that product formation in steady-state reactions is tightly coupled to electr… Show more

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Cited by 43 publications
(53 citation statements)
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References 34 publications
(73 reference statements)
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“…Such an arrangement can be formally expressed as α 3 α 3 . This arrangement still allowed for two Rieske and two mononuclear centers to be in proximity to each other, and account for our earlier findings on the stoichiometry of DHD formation during catalysis [8]. Because efforts to obtain the crystal structure of PDO so far have not been successful, we have attempted to clarify the question of the multimeric structure of PDO by other methods.…”
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confidence: 61%
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“…Such an arrangement can be formally expressed as α 3 α 3 . This arrangement still allowed for two Rieske and two mononuclear centers to be in proximity to each other, and account for our earlier findings on the stoichiometry of DHD formation during catalysis [8]. Because efforts to obtain the crystal structure of PDO so far have not been successful, we have attempted to clarify the question of the multimeric structure of PDO by other methods.…”
mentioning
confidence: 61%
“…On the other hand, E110, E210, and E220 would produce two molecules of product, and E111, E211, E221, and E222 would produce three molecules of DHD per 6 Rieske centers oxidized. Data presented in the table are based on the additional assumption vii) that all mononuclear centers are active, which is true at least for the WT enzyme used in both this study and previously [8]. Combined, the amounts of DHD produced for each possible distribution of Fe (II) among the iron mononuclear centers and the fractional content of these species determine the amount of DHD PDO hexamer would produce at each level of extrageneous free iron.…”
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confidence: 95%
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“…Oxygen reacts poorly with the ferrous mononuclear center if the Rieske center is not reduced, and the presence of substrate greatly enhances oxygen reactivity (9). The binding of NO to ferrous sites has been previously used as a model for oxygen binding in heme as well as in Rieske proteins (9)(10)(11). Certain caveats should be noted concerning the exact geometry of binding in the non-heme enzymes; for example, while the binding of oxygen in NDO was shown to be side-on to the mononuclear iron (12), the binding to NO was shown to occur in an end-on fashion (13).…”
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confidence: 99%
“…There are very few reports that describe the utilization of all three phthalate isomers as the carbon source by a single microbial strain (Vamsee-Krishna et al, 2006;Vamsee-Krishna & Phale, 2008;Wang et al, 1995). The first key step involved in the bacterial degradation of phthalate isomers is the double hydroxylation of the aromatic ring by the respective phthalate dioxygenase to yield a cis-dihydrodiol intermediate, which is further metabolized to aliphatic intermediates of the central carbon cycle via 3,4-dihydroxybenzoate (3,4-DHB) (Ballou & Batie, 1988;Batie et al, 1987;Schlafli et al, 1994;Tarasev & Ballou, 2005;Vamsee-Krishna et al, 2006).…”
Section: Introductionmentioning
confidence: 99%