Cis-1,2-dihydroxy-1,2-dihydronaphthalene: A bacterial metabolite from naphthalene

Some Properties of the Naphthalene Oxygenase from Pseudomonas sp. NCIB 9816

“…The pronounced similarity in these properties between the naphthalene oxygenase and metapyrocatechase is strong circumstantial evidence that naphthalene oxygenase is like metapyrocatechase and the similar ring-cleavage oxygenase from Pseudomonas ovalis, 3,4-dihydroxyphenylacetate 2,3-oxygenase (Kita, Miyake, Kamimoto, Senoh & Yamano, I 969), an Fe2+-dependent dioxygenase. That it is a dioxygenase would agree with the reports that the bacterial metabolism of naphthalene proceeds via formation of cis-I ,2-dihydroxy-r ,~-dihydronaphthalene (Catterall et al I 97 I ; Jerina et al 1971). It is probable that the cyclic peroxide proposed as an intermediate in this reaction (Jerina et al 1971) is not a distinct metabolic intermediate but rather a reaction intermediate, as has been proposed in both ortho-and meta-ring cleavage dioxygenase reactions, and that it is reduced to the cis-I ,z-dihydroxy-I ,z-dihydronaphthalene by NADH at the same active site; this is endorsed by our observation that there is no O2 uptake in the absence of NAD(P)H.…”

“…That it is a dioxygenase would agree with the reports that the bacterial metabolism of naphthalene proceeds via formation of cis-I ,2-dihydroxy-r ,~-dihydronaphthalene (Catterall et al I 97 I ; Jerina et al 1971). It is probable that the cyclic peroxide proposed as an intermediate in this reaction (Jerina et al 1971) is not a distinct metabolic intermediate but rather a reaction intermediate, as has been proposed in both ortho-and meta-ring cleavage dioxygenase reactions, and that it is reduced to the cis-I ,z-dihydroxy-I ,z-dihydronaphthalene by NADH at the same active site; this is endorsed by our observation that there is no O2 uptake in the absence of NAD(P)H.…”

“…This mechanism for naphthalene oxidation has been demonstrated in mammalian systems (Jerina, Daly, Witkop, ZaltzmanNirenberg & Udenfriend, 1970). However, in bacterial systems it has been shown that benzene (Gibson, Koch & Kallio, 1968), toluene (Gibson, Hensely, Yoshioka & Mabry, 1970) and naphthalene (Jerina, Daly, Jeffrey & Gibson, 1971) are converted to the cisdihydrodiols; in the case of benzene by a dioxygenase reaction (Gibson, Cardini, Maseles & Kallio, 1970).…”

Bacterial metabolism of side chain fluorinated aromatics: cometabolism of 3-trifluoromethyl(TFM)-benzoate by Pseudomonas putida (arvilla) mt-2 and Rhodococcus rubropertinctus n657

“…The fact that the unsubstituted organic parent compounds or methylsubstituted structural analogues are readily biodegraded under appropriate conditions (Gibson 1971;Dagley 1984), indicates that these structural eleroents impede biological breakdown. The mechanism of the biological persistence of halogenated aromatic compounds in bacteria has been investigated with halobenzoatesas model compounds (Dorn and Knackmuss 1978;Reineke and Knackmuss 1978a,b;Schmidt and Knackmuss 1980 ;Reineke et al 1982).…”

Genotoxicity studies of benzofuran dioxetanes and epoxides with isolated DNA, bacteria and mammalian cells

“…For example, they were postulatedas labile intermediates in the dioxygenase-activated aerobic metabolism of arenes. In particular, arenes, such as benzene [2] and naphthalene [3,4], and heteroarenes, such as benzofuran [5], are aerobically metabolized by the microorganism Pseudomonas putida to the corresponding cis-dihydrodiols and presumably proceeds through dioxetane intermediates. In the case of benzene [2], it was demonstrated by 18 0-labelled experiments that a dioxetane is indeed a plausible intermediate in this microbial oxidation [2] (Eqn.…”