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
Authors:
Open Access
- 1 February 1994
- journal article
- Published by American Society for Microbiology in Journal of Bacteriology
- Vol. 176 (3) , 789-795
Abstract
Angular dioxygenation has been established as the crucial step in dibenzofuran degradation by Brevibacterium sp. strain DPO 1361 (V. Strubel, K. H. Engesser, P. Fischer, and H.-J. Knackmuss, J. Bacteriol. 173:1932-1937, 1991). The same strain utilizes biphenyl and fluorene as sole sources of carbon and energy. The fluorene degradation sequence is proposed to be initiated by oxidation of the fluorene methylene group to 9-fluorenol. Cells grown on fluorene exhibit pronounced 9-fluorenol dehydrogenase activity. Angular dioxygenation of the 9-fluorenone thus formed yields 1,10-dihydro-1,10-dihydroxyfluoren-9-one (DDF). A mechanistic model is presented for the subsequent C-C bond cleavage by an NAD(+)-dependent DDF dehydrogenase, acting on the angular dihydrodiol. This enzyme was purified and characterized as a tetramer of four identical 40-kDa subunits. The following Km values were determined: 13 microM for DDF and 65 microM for 2,3-dihydro-2,3-dihydroxybiphenyl. The enzyme also catalyzes the production of 3-(2'-carboxyphenyl)catechol, which was isolated, and structurally characterized, in the form of the corresponding lactone, 4-hydroxydibenzo-(b,d)-pyran-6-one. Stoichiometry analysis unequivocally demonstrates that angular dioxygenation constitutes the principal pathway in Brevibacterium sp. strain DPO 1361.Keywords
This publication has 35 references indexed in Scilit:
- Dioxygenolytic cleavage of aryl ether bonds: 1,2-Dihydro-1,2-dihydroxy-4-carboxybenzophenone as evidence for initial 1,2-dioxygenation in 3- and 4-carboxy biphenyl ether degradationFEMS Microbiology Letters, 1990
- Dioxygenolytic cleavage of aryl ether bonds: 1,2-Dihydro-1,2-dihydroxy-4-carboxybenzophenone as evidence for initial 1,2-dioxygenation in 3- and 4-carboxy biphenyl ether degradationFEMS Microbiology Letters, 1990
- Bacterial degradation of 3- and 4-carboxybiphenyl ether by Psuedomonas sp. NSS2FEMS Microbiology Letters, 1990
- Dioxygenolytic cleavage of aryl ether bonds: 1, 10-dihydro-1, 10-dihydroxyfluoren-9-one, a novel arene dihydrodiol as evidence for angular dioxygenation of dibenzofuranFEMS Microbiology Letters, 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 dibenzofuranFEMS Microbiology Letters, 1989
- Degradation of 2-bromo-, 2-chloro- and 2-fluorobenzoate by Pseudomonas putida CLB 250FEMS Microbiology Letters, 1989
- Degradation of 2-bromo-, 2-chloro- and 2-fluorobenzoate byPseudomonas putidaCLB 250FEMS Microbiology Letters, 1989
- Enrichment of dibenzofuran utilizing bacteria with high co-metabolic potential towards dibenzodioxin and other anellated aromaticsFEMS Microbiology Letters, 1989
- Benzylic monooxygenation catalyzed by toluene dioxygenase from Pseudomonas putidaBiochemistry, 1988
- Über Chlorderivate des Brenzcatechins und des o‐ChinonsEuropean Journal of Inorganic Chemistry, 1911