Skip to main content

Aerobic Degradation of Aromatic Hydrocarbons

  • Reference work entry
  • First Online:
Aerobic Utilization of Hydrocarbons, Oils, and Lipids

Abstract

Aromatic hydrocarbons are widely distributed in nature. They are found as lignin components, aromatic amino acids and xenobiotic compounds, among others. Microorganisms, mostly bacteria, degrade an impressive variety of such chemical structures. The major principle of aromatic hydrocarbon biodegradation is that a broad range of aromatic hydrocarbons are transformed by peripheral reactions to a restricted range of central intermediates, which are subject to ring-cleavage and funneling into the Krebs cycle. Key enzymes in aerobic aromatic degradation are oxygenases, preparing aromatics for ring-cleavage by the introduction of hydroxyl functions and catalyzing cleavage of the aromatic ring. The diverse monooxygenases and dioxygenases involved in hydroxylations, a significant proportion of them possessing relaxed substrate specificity, are discussed as well as the broad diversity of side chain processing transformations involved in the formation of ring-cleavage central intermediates. Ring cleavage dioxygenases, covering intradiol ring cleavage of ortho dihydroxylated intermediates, and a large number of diverse but mechanistically related extradiol dioxygenases participating in ring cleavage of ortho and para dihydroxylated intermediates are also discussed. CoA dependent aerobic routes to allow ring-cleavage of aromatic hydrocarbons without involvement of dihydroxylated aromatic intermediates have been described in the last years and are also reviewed. The degradation of heteroarenes will not be described in this chapter.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 239.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 279.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  • Abe T, Masai E, Miyauchi K, Katayama Y, Fukuda M (2005) A tetrahydrofolate-dependent O-demethylase, LigM, is crucial for catabolism of vanillate and syringate in Sphingomonas paucimobilis SYK-6. J Bacteriol 187:2030–2037

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Altenschmidt U, Fuchs G (1992) Novel aerobic 2-aminobenzoate metabolism. Purification and characterization of 2-aminobenzoate-CoA ligase, localization of the genes on a 8-kbp plasmid, and cloning and sequencing of the genes from a denitrifying Pseudomonas sp. Eur J Biochem 205:721–727

    Article  CAS  PubMed  Google Scholar 

  • Altenschmidt U, Oswald B, Steiner E, Herrmann H, Fuchs G (1993) New aerobic benzoate oxidation pathway via benzoyl-Coenzyme A and 3-hydroxybenzoyl-Coenzyme A in a denitrifying Pseudomonas sp. J Bacteriol 175:4851–4858

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Arias-Barrau E, Olivera ER, Luengo JM, Fernandez C, Galan B, Garcia JL, Diaz E, Minambres B (2004) The homogentisate pathway: a central catabolic pathway involved in the degradation of L-phenylalanine, L-tyrosine, and 3-hydroxyphenylacetate in Pseudomonas putida. J Bacteriol 186:5062–5077

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Arias-Barrau E, Sandoval A, Naharro G, Olivera ER, Luengo JM (2005) A two-component hydroxylase involved in the assimilation of 3-hydroxyphenylacetate in Pseudomonas putida. J Biol Chem 280:26435–26447

    Article  CAS  PubMed  Google Scholar 

  • Armengaud J, Timmis KN, Wittich RM (1999) A functional 4-hydroxysalicylate/hydroxyquinol degradative pathway gene cluster is linked to the initial dibenzo-p-dioxin pathway genes in Sphingomonas sp strain RW1. J Bacteriol 181:3452–3461

    CAS  PubMed  PubMed Central  Google Scholar 

  • Assinder SJ, Williams PA (1990) The TOL plasmids: determinants of the catabolism of toluene and the xylenes. Adv Microb Physiol 31:1–69

    Article  CAS  PubMed  Google Scholar 

  • Babbitt PC, Hasson MS, Wedekind JE, Palmer DRJ, Barrett WC, Reed GH, Rayment I, Ringe D, Kenyon GL, Gerlt JA (1996) The enolase superfamily: a general strategy for enzyme-catalyzed abstraction of the alpha-protons of carboxylic acids. Biochemistry 35:16489–16501

    Article  CAS  PubMed  Google Scholar 

  • Bains J, Boulanger MJ (2007) Biochemical and structural characterization of the paralogous benzoate CoA ligases from Burkholderia xenovorans LB400: defining the entry point into the novel benzoate oxidation (box) pathway. J Mol Biol 373:965–977

    Article  CAS  PubMed  Google Scholar 

  • Ballou DP, Entsch B, Cole LJ (2005) Dynamics involved in catalysis by single-component and two-component flavin-dependent aromatic hydroxylases. Biochem Biophys Res Commun 338:590–598

    Article  CAS  PubMed  Google Scholar 

  • Barnes MR, Duetz WA, Williams PA (1997) A 3-(3-hydroxyphenyl)propionic acid catabolic pathway in Rhodococcus globerulus PWD1: cloning and characterization of the hpp operon. J Bacteriol 179:6145–6153

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Batie CJ, LaHaie E, Ballou DP (1987) Purification and characterization of phthalate oxygenase and phthalate oxygenase reductase from Pseudomonas cepacia. J Biol Chem 262:1510–1518

    CAS  PubMed  Google Scholar 

  • Beltrametti F, Marconi AM, Bestetti G, Colombo C, Galli E, Ruzzi M, Zennaro E (1997) Sequencing and functional analysis of styrene catabolism genes from Pseudomonas fluorescens ST. Appl Environ Microbiol 63:2232–2239

    CAS  PubMed  PubMed Central  Google Scholar 

  • Bertoni G, Martino M, Galli E, Barbieri P (1998) Analysis of the gene cluster encoding toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1. Appl Environ Microbiol 64:3626–3632

    CAS  PubMed  PubMed Central  Google Scholar 

  • Bosch R, Moore ERB, GarciaValdes E, Pieper DH (1999) NahW, a novel, inducible salicylate hydroxylase involved in mineralization of naphthalene by Pseudomonas stutzeri AN10. J Bacteriol 181:2315–2322

    CAS  PubMed  PubMed Central  Google Scholar 

  • Bruce NC, Cain RB, Pieper DH, Engesser K-H (1989) Purification and characterization of 4-methylmuconolactone methyl-isomerase, a novel enzyme of the modified 3-oxoadipate pathway in nocardioform actionomycetes. Biochem J 262:303–312

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Buder R, Fuchs G (1989) 2-Aminobenzoyl-CoA monooxygenase/reductase, a novel type of flavoenzyme. Purification and some properties of the enzyme. Eur J Biochem 185:629–635

    Article  CAS  PubMed  Google Scholar 

  • Bundy BM, Campbell AL, Neidle EL (1998) Similarities between the antABC-encoded anthranilate dioxygenase and the benABC-encoded benzoate dioxygenase of Acinetobacter sp. strain ADP1. J Bacteriol 180:4466–4474

    CAS  PubMed  PubMed Central  Google Scholar 

  • Buswell JA, Ribbons DW (1988) Vanillate O-demethylase from Pseudomonas species. Methods Enzymol 161:294–301

    Article  CAS  PubMed  Google Scholar 

  • Cafaro V, Izzo V, Scognamiglio R, Notomista E, Capasso P, Casbarra A, Pucci P, Di Donato A (2004) Phenol hydroxylase and toluene/o-xylene monooxygenase from Pseudomonas stutzeri OX1: interplay between two enzymes. Appl Environ Microbiol 70:2211–2219

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Camara B, Bielecki P, Kaminski F, dos Santos VM, Plumeier I, Nikodem P, Pieper DH (2007) A gene cluster involved in degradation of substituted salicylates via ortho cleavage in Pseudomonas sp. strain MT1 encodes enzymes specifically adapted for transformation of 4-methylcatechol and 3-methylmuconate. J Bacteriol 189:1664–1674

    Article  CAS  PubMed  Google Scholar 

  • Catelani D, Fiecchi A, Galli E (1971) (+)-γ-Carboxymethyl-γ-methyl-Δα-butenolide. A 1,2 ring-fission product of 4-methylcatechol by Pseudomonas desmolyticum. Biochem J 121:89–92

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Cha CJ, Cain RB, Bruce NC (1998) The modified beta-ketoadipate pathway in Rhodococcus rhodochrous N75: enzymology of 3-methylmuconolactone metabolism. J Bacteriol 180:6668–6673

    CAS  PubMed  PubMed Central  Google Scholar 

  • Chang HK, Zylstra GJ (1998) Novel organization of the genes for phthalate degradation from Burkholderia cepacia DBO1. J Bacteriol 180:6529–6537

    CAS  PubMed  PubMed Central  Google Scholar 

  • Chang HK, Mohseni P, Zylstra GJ (2003) Characterization and regulation of the genes for a novel anthranilate 1,2-dioxygenase from Burkholderia cepacia DBO1. J Bacteriol 185:5871–5881

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Crawford RL (1976) Degradation of homogentisate by strains of Bacillus and Moraxella. Can J Microbiol 22:276–280

    Article  CAS  PubMed  Google Scholar 

  • Crawford RL (1978) Hydroxylation of 4-hydroxyphenoxyacetate by a Bacillus sp. FEMS Microbiol Lett 4:233–234

    Article  CAS  Google Scholar 

  • Crawford RL, Frick TD (1977) Rapid spectrophotometric differentiation between glutathione-dependent and glutathione-independent gentisate and homogentisate pathways. Appl Environ Microbiol 34:170–174

    CAS  PubMed  PubMed Central  Google Scholar 

  • Crawford RL, Hutton SW, Chapman PJ (1975) Purification and properties of gentisate 1,2-dioxygenase from Moraxella osloensis. J Bacteriol 121:794–799

    CAS  PubMed  PubMed Central  Google Scholar 

  • Cronin CN, Kim J, Fuller JH, Zhang X, McIntire WS (1999) Organization and sequences of p-hydroxybenzaldehyde dehydrogenase and other plasmid-encoded genes for early enzymes of the p-cresol degradative pathway in Pseudomonas putida NCIMB 9866 and 9869. DNA Seq 10:7–17

    Article  CAS  PubMed  Google Scholar 

  • Darby JM, Taylor DG, Hopper DJ (1987) Hydroquinone as a ring-fission substrate in the catabolism of 4-ethylphenol and 4-hydroxyacetophenone by Pseudomonas putida JD1. J Gen Microbiol 133:2137–2146

    CAS  Google Scholar 

  • DeFrank JJ, Ribbons DW (1976) The p-cymene pathway in Pseudomonas putida PL: isolation of a dihydrodiol accumulated by a mutant. Biochem Biophys Res Commun 70:1129–1135

    Article  CAS  PubMed  Google Scholar 

  • Diaz E, Ferrandez A, Prieto MA, Garcia JL (2001) Biodegradation of aromatic compounds by Escherichia coli. Microbiol Mol Biol Rev 65:523–569

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Duarte M, Jauregui R, Vilchez-Vargas R, Junca H, Pieper DH (2014) AromaDeg, a novel database for phylogenomics of aerobic degradation of aromatics. Database 2014; bau118

    Google Scholar 

  • Dunwell JM, Khuri S, Gane PJ (2000) Microbial relatives of the seed storage proteins of higher plants: conservation of structure and diversification of function during evolution of the cupin superfamily. Microbiol Mol Biol Rev 64:153–179

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Eaton RW (1996) p-Cumate catabolic pathway in Pseudomonas putida F1: cloning and characterization of DNA carrying the cmt operon. J Bacteriol 178:1351–1362

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Eaton RW (1997) p-Cymene catabolic pathway in Pseudomonas putida F1: cloning and characterization of DNA encoding conversion of p-cymene to p-cumate. J Bacteriol 179:3171–3180

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Eaton RW (2001) Plasmid-encoded phthalate catabolic pathway in Arthrobacter keyseri 12B. J Bacteriol 183:3689–3703

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Eby DM, Beharry ZM, Coulter ED, Kurtz DM, Neidle EL (2001) Characterization and evolution of anthranilate 1,2-dioxygenase from Acinetobacter sp. strain ADP1. J Bacteriol 183:109–118

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Eltis LD, Bolin JT (1996) Evolutionary relationships among extradiol dioxygenases. J Bacteriol 178:5930–5937

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Entsch B, van Berkel WJ (1995) Structure and mechanism of para-hydroxybenzoate hydroxylase. FASEB J 9:476–483

    Article  CAS  PubMed  Google Scholar 

  • Entsch B, Massey V, Claiborne A (1987) p-Hydroxybenzoate hydroxylase containing 6-hydroxy-FAD is an effective enzyme with modified reaction mechanisms. J Biol Chem 262:6060–6068

    CAS  PubMed  Google Scholar 

  • Eulberg D, Golovleva LA, Schlomann M (1997) Characterization of catechol catabolic genes from Rhodococcus erythropolis 1CP. J Bacteriol 179:370–381

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Eulberg D, Lakner S, Golovleva LA, Schlomann M (1998) Characterization of a protocatechuate catabolic gene cluster from Rhodococcus opacus 1CP: evidence for a merged enzyme with 4-carboxymuconolactone-decarboxylating and 3-oxoadipate enol-lactone-hydrolyzing activity. J Bacteriol 180:1072–1081

    CAS  PubMed  PubMed Central  Google Scholar 

  • Farrow JM, Pesci EC (2007) Two distinct pathways supply anthranilate as a precursor of the Pseudomonas quinolone signal. J Bacteriol 189:3425–3433

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Fernandez C, Ferrandez A, Minambres B, Diaz E, Garcia JL (2006) Genetic characterization of the phenylacetyl-coenzyme A oxygenase from the aerobic phenylacetic acid degradation pathway of Escherichia coli. Appl Environ Microbiol 72:7422–7426

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ferrández A, Garciá JL, Díaz E (1997) Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12. J Bacteriol 179:2573–2581

    Article  PubMed  PubMed Central  Google Scholar 

  • Ferrandez A, Minambres B, Garcia B, Olivera ER, Luengo JM, Garcia JL, Diaz E (1998) Catabolism of phenylacetic acid in Escherichia coli – Characterization of a new aerobic hybrid pathway. J Biol Chem 273:25974–25986

    Article  CAS  PubMed  Google Scholar 

  • Ferraroni M, Seifert J, Travkin VM, Thiel M, Kaschabek S, Scozzafava A, Golovleva L, Schlomann M, Briganti F (2005) Crystal structure of the hydroxyquinol 1,2-dioxygenase from Nocardioides simplex 3E, a key enzyme involved in polychlorinated aromatics biodegradation. J Biol Chem 280:21144–21154

    Article  CAS  PubMed  Google Scholar 

  • Fishman A, Tao Y, Wood TK (2004) Toluene 3-monooxygenase of Ralstonia pickettii PKO1 is a para-hydroxylating enzyme. J Bacteriol 186:3117–3123

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Fishman A, Tao Y, Rui L, Wood TK (2005) Controlling the regiospecific oxidation of aromatics via active site engineering of toluene para-monooxygenase of Ralstonia pickettii PKO1. J Biol Chem 280:506–514

    Article  CAS  PubMed  Google Scholar 

  • Fitzpatrick PF (2003) Mechanism of aromatic amino acid hydroxylation. Biochemistry 42:14083–14091

    Article  CAS  PubMed  Google Scholar 

  • Fu WJ, Oriel P (1998) Gentisate 1,2-dioxygenase from Haloferax sp. D1227. Extremophiles 2:439–446

    Article  CAS  PubMed  Google Scholar 

  • Fuenmayor SL, Wild M, Boyes AL, Williams PA (1998) A gene cluster encoding steps in conversion of naphthalene to gentisate in Pseudomonas sp. strain U2. J Bacteriol 180:2522–2530

    CAS  PubMed  PubMed Central  Google Scholar 

  • Fujisawa H, Hayaishi O (1968) Protocatechuate 3,4-dioxygenase. I. Crystallization and characterization. J Biol Chem 243:2673–2681

    CAS  PubMed  Google Scholar 

  • Fukumori F, Saint CP (1997) Nucleotide sequences and regulational analysis of genes involved in conversion of aniline to catechol in Pseudomonas putida UCC22(pTDN1). J Bacteriol 179:399–408

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Gasson MJ, Kitamura Y, McLauchlan WR, Narbad A, Parr AJ, Lindsay E, Parsons H, Payne J, Rhodes MJC, Walton NJ (1998) Metabolism of ferulic acid to vanillin – A bacterial gene of the enoyl-SCoA hydratase/isomerase superfamily encodes an enzyme for the hydration and cleavage of a hydroxycinnamic acid SCoA thioester. J Biol Chem 273:4163–4170

    Article  CAS  PubMed  Google Scholar 

  • Gerlt JA, Babbitt PC (2001) Divergent evolution of enzymatic function: mechanistically diverse superfamilies and functionally distinct suprafamilies. Annu Rev Biochem 70:209–246

    Article  CAS  PubMed  Google Scholar 

  • Gescher J, Eisenreich W, Worth J, Bacher A, Fuchs G (2005) Aerobic benzoyl-CoA catabolic pathway in Azoarcus evansii: studies on the non-oxygenolytic ring cleavage enzyme. Mol Microbiol 56:1586–1600

    Article  CAS  PubMed  Google Scholar 

  • Gescher J, Ismail W, Olgeschlager E, Eisenreich W, Worth J, Fuchs G (2006) Aerobic benzoyl-coenzyme A (CoA) catabolic pathway in Azoarcus evansii: conversion of ring cleavage product by 3,4-dehydroadipyl-CoA semialdehyde dehydrogenase. J Bacteriol 188:2919–2927

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Gibson DT, Parales RE (2000) Aromatic hydrocarbon dioxygenases in environmental biotechnology. Curr Opin Biotechnol 11:236–243

    Article  CAS  PubMed  Google Scholar 

  • Gibson DT, Koch JR, Kallio RE (1968) Oxidative degradation of aromatic hydrocarbons by microorganisms. 1. Enzymatic formation of catechol from benzene. Biochemistry 7:2653–2662

    Article  CAS  PubMed  Google Scholar 

  • Gobel M, Kassel-Cati K, Schmidt E, Reineke W (2002) Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: cloning, characterization, and analysis of sequences encoding 3-oxoadipate: succinyl-coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase. J Bacteriol 184:216–223

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Gu W, Song J, Bonner CA, Xie G, Jensen RA (1998) PhhC is an essential aminotransferase for aromatic amino acid catabolism in Pseudomonas aeruginosa. Microbiology 144:3127–3134

    Article  CAS  PubMed  Google Scholar 

  • Halak S, Basta T, Burger S, Contzen M, Wray V, Pieper DH, Stolz A (2007) 4-Sulfomuconolactone hydrolases from Hydrogenophaga intermedia S1 and Agrobacterium radiobacter S2. J Bacteriol 189:6998–7006

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hara H, Masai E, Katayama Y, Fukuda M (2000) The 4-oxalomesaconate hydratase gene, involved in the protocatechuate 4,5-cleavage pathway, is essential to vanillate and syringate degradation in Sphingomonas paucimobilis SYK-6. J Bacteriol 182:6950–6957

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Harayama S, Rekik M (1989) Bacterial aromatic ring-cleavage enzymes are classified into two different gene families. J Biol Chem 264:15328–15333

    CAS  PubMed  Google Scholar 

  • Harayama S, Leppik RA, Rekik M, Mermod M, Lehrbach PR, Reineke W, Timmis KN (1986) Gene order of the TOL catabolic plasmid upper pathway operon and oxidation of both toluene and benzyl alcohol by the xylA product. J Bacteriol 167:455–461

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Harayama S, Mermod N, Rekik M, Lehrbach PR, Timmis KN (1987) Roles of the divergent branches of the meta-cleavage pathway in the degradation of benzoate and substituted benzoates. J Bacteriol 169:558–564

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hareland WA, Crawford RL, Chapman PJ, Dagley S (1975) Metabolic function and properties of 4-hydroxyphenylacetic acid 1-hydroxylase from Pseudomonas acidovorans. J Bacteriol 121:272–285

    CAS  PubMed  PubMed Central  Google Scholar 

  • Harpel MR, Lipscomb JD (1990) Gentisate 1,2-dioxygenase from Pseudomonas. Substrate coordination of the active site Fe2+ and mechanism of turnover. J Biol Chem 265:22187–22196

    CAS  PubMed  Google Scholar 

  • Harwood CS, Parales RE (1996) The beta-ketoadipate pathway and the biology of self-identity. Annu Rev Microbiol 50:553–590

    Article  CAS  PubMed  Google Scholar 

  • Hatta T, Mukerjee-Dhar G, Damborsky J, Kiyohara H, Kimbara K (2003) Characterization of a novel thermostable Mn(II)-dependent 2,3-dihydroxybiphenyl 1,2-dioxygenase from a polychlorinated biphenyl- and naphthalene-degrading Bacillus sp. JF8. J Biol Chem 278:21483–21492

    Article  CAS  PubMed  Google Scholar 

  • He ZG, Spain JC (1998) A novel 2-Aminomuconate deaminase in the nitrobenzene degradation pathway of Pseudomonas pseudoalcaligenes JS45. J Bacteriol 180:2502–2506

    CAS  PubMed  PubMed Central  Google Scholar 

  • He ZQ, Davis JK, Spain JC (1998) Purification, characterization, and sequence analysis of 2-aminomuconic 6-semialdehyde dehydrogenase from Pseudomonas pseudoalcaligenes JS45. J Bacteriol 180:4591–4595

    CAS  PubMed  PubMed Central  Google Scholar 

  • Hintner JP, Lechner C, Riegert U, Kuhm AE, Storm T, Reemtsma T, Stolz A (2001) Direct ring fission of salicylate by a salicylate 1,2- dioxygenase activity from Pseudaminobacter salicylatoxidans. J Bacteriol 183:6936–6942

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hiromoto T, Fujiwara S, Hosokawa K, Yamaguchi H (2006) Crystal structure of 3-hydroxybenzoate hydroxylase from Comamonas testosteroni has a large tunnel for substrate and oxygen access to the active site. J Mol Biol 364:878–896

    Article  CAS  PubMed  Google Scholar 

  • Hopper DJ (1976) The hydroxylation of p-cresol and its conversion to p-hydroxybenzaldehyde in Pseudomonas putida. Biochem Biophys Res Commun 69:462–468

    Article  CAS  PubMed  Google Scholar 

  • Hopper D, Taylor DG (1977) The purification and properties of p-cresol-(acceptor) oxidoreductase (hydroxylating), a flavocytochrome from Pseudomonas putida. Biochem J 187:155–162

    Article  Google Scholar 

  • Hopper D, Chapman PJ, Dagley S (1971) The enzymatic degradation of alkyl-substituted gentisates, maleates and malates. Biochem J 122:29–40

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Huang Y, Zhao KX, Shen XH, Chaudhry MT, Jiang CY, Liu SJ (2006) Genetic characterization of the resorcinol catabolic pathway in Corynebacterium glutamicum. Appl Environ Microbiol 72:7238–7245

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hugo N, Armengaud J, Gaillard J, Timmis KN, Jouanneau Y (1998) A novel [2Fe-2S] ferredoxin from Pseudomonas putida mt-2 promotes the reductive reactivation of catechol 2,3-dioxygenase. J Biol Chem 273:9622–9629

    Article  CAS  PubMed  Google Scholar 

  • Ishiyama D, Vujaklija D, Davies J (2004) Novel pathway of salicylate degradation by Streptomyces sp. strain WA46. Appl Environ Microbiol 70:1297–1306

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ismail W, El-Said Mohamed M, Wanner BL, Datsenko KA, Eisenreich W, Rohdich F, Bacher A, Fuchs G (2003) Functional genomics by NMR spectroscopy. Phenylacetate catabolism in Escherichia coli. Eur J Biochem 270:3047–3054

    Article  CAS  PubMed  Google Scholar 

  • Iwabuchi T, Harayama S (1998) Biochemical and molecular characterization of 1-hydroxy-2-naphthoate dioxygenase from Nocardioides sp. KP7. J Biol Chem 273:8332–8336

    Article  CAS  PubMed  Google Scholar 

  • Jouanneau Y, Micoud J, Meyer C (2007) Purification and characterization of a three-component salicylate 1-hydroxylase from Sphingomonas sp. strain CHY-1. Appl Environ Microbiol 73:7515–7521

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Karlson U, Dwyer DF, Hooper SW, Moore ERB, Timmis KN, Eltis LD (1993) Two independently regulated cytochromes P-450 in a Rhodococcus rhodochrous strain that degrades 2-ethoxyphenol and 4-methoxybenzoate. J Bacteriol 175:1467–1474

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kasai D, Masai E, Miyauchi K, Katayama Y, Fukuda M (2004) Characterization of the 3- O-methylgallate dioxygenase gene and evidence of multiple 3- O-methylgallate catabolic pathways in Sphingomonas paucimobilis SYK-6. J Bacteriol 186:4951–4959

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kasai D, Masai E, Miyauchi K, Katayama Y, Fukuda M (2005) Characterization of the gallate dioxygenase gene: three distinct ring cleavage dioxygenases are involved in syringate degradation by Sphingomonas paucimobilis SYK-6. J Bacteriol 187:5067–5074

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Keat MJ, Hopper DJ (1978) p-Cresol and 3,5-xylenol methylhydroxylases in Pseudomonas putida N.C.I.B. 9869. Biochem J 175:649–658

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Kirk TK, Farrell RL (1987) Enzymatic “combustion”: the microbial degradation of lignin. Annu Rev Microbiol 41:465–505

    Article  CAS  PubMed  Google Scholar 

  • Kurnasov O, Jablonski L, Polanuyer B, Dorrestein P, Begley T, Osterman A (2003a) Aerobic tryptophan degradation pathway in bacteria: novel kynurenine formamidase. FEMS Microbiol Lett 227:219–227

    Article  CAS  PubMed  Google Scholar 

  • Kurnasov O, Goral V, Colabroy K, Gerdes S, Anantha S, Osterman A, Begley TP (2003b) NAD biosynthesis: identification of the tryptophan to quinolinate pathway in bacteria. Chem Biol 10:1195–1204

    Article  CAS  PubMed  Google Scholar 

  • Lam WWY, Bugg TDH (1997) Purification, characterization, and stereochemical analysis of a C-C hydrolase: 2-hydroxy-6-keto-nona-2,4-diene-1,9-dioic acid 5,6-hydrolase. Biochemistry 36:12242–12251

    Article  CAS  PubMed  Google Scholar 

  • Leahy JG, Batchelor PJ, Morcomb SM (2003) Evolution of the soluble diiron monooxygenases. FEMS Microbiol Rev 27:449–479

    Article  CAS  PubMed  Google Scholar 

  • Lee J-H, Omori T, Kodama T (1994) Identification of the metabolic intermediates of phthalate by Tn5 mutants of Pseudomonas testosteroni and analysis of the 4,5-dihydroxyphthalate decarboxylase gene. J Ferment Bioeng 77:583–590

    Article  CAS  Google Scholar 

  • Lehrbach PR, Zeyer J, Reineke W, Knackmuss HJ, Timmis KN (1984) Enzyme recruitment in vitro: use of cloned genes to extend the range of haloaromatics degraded by Pseudomonas sp. strain B13. J Bacteriol 158:1025–1032

    CAS  PubMed  PubMed Central  Google Scholar 

  • Liang Q, Takeo M, Chen M, Zhang W, Xu Y, Lin M (2005) Chromosome-encoded gene cluster for the metabolic pathway that converts aniline to TCA-cycle intermediates in Delftia tsuruhatensis AD9. Microbiology 151:3435–3446

    Article  CAS  PubMed  Google Scholar 

  • Lipscomb JD, Orville AM (1992) Mechanistic aspects of dihydroxybenzoate dioxygenases. In: Sigel H, Sigel A (eds) Metal ions in biological systems. Marcel Dekker Inc., New York, pp 243–298

    Google Scholar 

  • Liu L, Wu JF, Ma YF, Wang SY, Zhao GP, Liu SJ (2007) A novel deaminase involved in chloronitrobenzene and nitrobenzene degradation with Comamonas sp. strain CNB-1. J Bacteriol 189:2677–2682

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Marin M, Perez-Pantoja D, Donoso R, Wray V, Gonzalez B, Pieper DH (2010). Modified 3-oxoadipate pathway for the biodegradation of methylaromatics in Pseudomonas reinekei MT1. J Bacteriol 192:1543–1552

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Maruyama K (1983) Purification and properties of 2-pyrone-4,6-dicarboxylate hydrolase. J Biochem 93:557–565

    Article  CAS  PubMed  Google Scholar 

  • Masai E, Katayama Y, Nishikawa S, Fukuda M (1999a) Characterization of Sphingomonas paucimobilis SYK-6 genes involved in degradation of lignin-related compounds. J Ind Microbiol Biotechnol 23:364–373

    Article  CAS  PubMed  Google Scholar 

  • Masai E, Shinohara S, Hara H, Nishikawa S, Katayama Y, Fukuda M (1999b) Genetic and biochemical characterization of a 2-pyrone-4,6-dicarboxylic acid hydrolase involved in the protocatechuate 4,5-cleavage pathway of Sphingomonas paucimobilis SYK-6. J Bacteriol 181:55–62

    CAS  PubMed  PubMed Central  Google Scholar 

  • Masai E, Sasaki M, Minakawa Y, Abe T, Sonoki T, Miyauchi K, Katayama Y, Fukuda M (2004) A novel tetrahydrofolate-dependent O-demethylase gene is essential for growth of Sphingomonas paucimobilis SYK-6 with syringate. J Bacteriol 186:2757–2765

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Matera I, Ferraroni M, Bürger S, Scozzafava A, Stolz A, Briganti F (2008) Salicylate 1,2-dioxygenase from Pseudaminobacter salicylatoxidans: crystal structure of a peculiar ring-cleaving dioxygenase. J Mol Biol 380:856–868

    Article  CAS  PubMed  Google Scholar 

  • McIntire W, Hopper DJ, Singer TP (1985) p-Cresol methylhydroxylase. Biochem J 228:325–335

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Mohamed ME (2000) Biochemical and molecular characterization of phenylacetate-coenzyme A ligase, an enzyme catalyzing the first step in aerobic metabolism of phenylacetic acid in Azoarcus evansii. J Bacteriol 182:286–294

    Article  CAS  Google Scholar 

  • Moonen MJ, Kamerbeek N, Westphal AH, Boeren SA, Janssen DB, Fraaije MW, van Berkel WJ (2008a) Elucidation of the 4-hydroxyacetophenone catabolic pathway in Pseudomonas fluorescens ACB. J Bacteriol 190:5190–5198

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Moonen MJ, Synowsky SA, van den Berg WA, Westphal AH, Heck AJ, van den Heuvel RH, Fraaije MW, van Berkel WJ (2008b) Hydroquinone dioxygenase from Pseudomonas fluorescens ACB: a novel member of the family of nonheme-iron(II)-dependent dioxygenases. J Bacteriol 190:5199–5209

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Moran GR (2005) 4-Hydroxyphenylpyruvate dioxygenase. Arch Biochem Biophys 433:117–128

    Article  CAS  PubMed  Google Scholar 

  • Morawski B, Segura A, Ornston LN (2000) Substrate range and genetic analysis of Acinetobacter vanillate demethylase. J Bacteriol 182:1383–1389

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Murakami S, Sawami Y, Takenaka S, Aoki K (2004) Cloning of a gene encoding 4-amino-3-hydroxybenzoate 2,3-dioxygenase from Bordetella sp. 10d. Biochem Biophys Res Commun 314:489–494

    Article  CAS  PubMed  Google Scholar 

  • Muraki T, Taki M, Hasegawa Y, Iwaki H, Lau PCK (2003) Prokaryotic homologs of the eukaryotic 3-hydroxyanthranilate 3,4-dioxygenase and 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase in the 2-nitrobenzoate degradation pathway of Pseudomonas fluorescens strain KU-7. Appl Environ Microbiol 69:1564–1572

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Nakata H, Yamauchi T, Fujisawa H (1979) Phenylalanine hydroxylase from Chromobacterium violaceum Purification and characterization. J Biol Chem 254:1829–1833

    CAS  PubMed  Google Scholar 

  • Nakazawa T, Hayashi E (1978) Phthalate and 4-hydroxyphthalate metabolism in Pseudomonas testosteroni: purification and properties of 4,5-dihydroxyphthalate decarboxylase. Appl Environ Microbiol 36:264–269

    CAS  PubMed  PubMed Central  Google Scholar 

  • Newman LM, Wackett LP (1995) Purification and characterization of toluene 2-monooxygenase from Burkholderia cepacia G4. Biochemistry 34:14066–14076

    Article  CAS  PubMed  Google Scholar 

  • Ng LC, Shingler V, Sze CC, Poh CL (1994) Cloning and sequences of the first eight genes of the chromosomally encoded (methyl) phenol degradation pathway from Pseudomonas putida P35X. Gene 151:29–36

    Article  CAS  PubMed  Google Scholar 

  • Nogales J, Canales A, Jimenez-Barbero J, Garcia JL, Diaz E (2005) Molecular characterization of the gallate dioxygenase from Pseudomonas putida KT2440. The prototype of a new subgroup of extradiol dioxygenases. J Biol Chem 280:35382–35390

    Article  CAS  PubMed  Google Scholar 

  • Nogales J, Macchi R, Franchi F, Barzaghi D, Fernández C, García JL, Bertoni G, Díaz E (2007) Characterization of the last step of the aerobic phenylacetic acid degradation pathway. Microbiology 153:357–365

    Article  CAS  PubMed  Google Scholar 

  • Nurk A, Kasak L, Kivisaar M (1991) Sequence of the gene (pheA) encoding phenol monooxygenae from Pseudomonas sp. EST1001: expression in Escherichia coli and Pseudomonas putida. Gene 102:13–18

    Article  CAS  PubMed  Google Scholar 

  • Olivera ER, Minambres B, Garcia B, Muniz C, Moreno MA, Ferrandez A, Diaz E, Garcia JL, Luengo JM (1998) Molecular characterization of the phenylacetic acid catabolic pathway in Pseudomonas putida U: the phenylacetyl-CoA catabolon. Proc Natl Acad Sci USA 95:6419–6424

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Olsen RH, Kukor JJ, Kaphammer B (1994) A novel toluene-3-monooxygenase pathway cloned from Pseudomonas pickettii PKO1. J Bacteriol 176:3749–3756

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Ono K, Nozaki M, Hayaishi O (1970) Purification and some properties of protocatechuate 4,5-dioxygenase. Biochim Biophys Acta 220:224–238

    Article  CAS  PubMed  Google Scholar 

  • Orii C, Takenaka S, Murakami S, Aoki K (2004) A novel coupled enzyme assay reveals an enzyme responsible for the deamination of a chemically unstable intermediate in the metabolic pathway of 4-amino-3-hydroxybenzoic acid in Bordetella sp. strain 10d. Eur J Biochem 271:3248–3254

    Article  CAS  PubMed  Google Scholar 

  • Overhage J, Priefert H, Steinbuchel A (1999) Biochemical and genetic analyses of ferulic acid catabolism in Pseudomonas sp strain HR199. Appl Environ Microbiol 65:4837–4847

    CAS  PubMed  PubMed Central  Google Scholar 

  • Peng X, Masai E, Kitayama H, Harada K, Katayama Y, Fukuda M (2002) Characterization of the 5-carboxyvanillate decarboxylase gene and its role in lignin-related biphenyl catabolism in Sphingomonas paucimobilis SYK-6. Appl Environ Microbiol 68:4407–4415

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Peng X, Masai E, Kasai D, Miyauchi K, Katayama Y, Fukuda M (2005) A second 5-carboxyvanillate decarboxylase gene, ligW2, is important for lignin-related biphenyl catabolism in Sphingomonas paucimobilis SYK-6. Appl Environ Microbiol 71:5014–5021

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Perez-Pantoja D, De la Iglesia R, Pieper DH, Gonzalez B (2008) Metabolic reconstruction of aromatic compounds degradation from the genome of the amazing pollutant degrading bacterium Cupriavidus necator JMP134. FEMS Microbiol Rev 32:736–794

    Article  CAS  PubMed  Google Scholar 

  • Pieper DH, Engesser K-H, Don RH, Timmis KN, Knackmuss H-J (1985) Modified ortho-cleavage pathway in Alcaligenes eutrophus JMP134 for the degradation of 4-methylcatechol. FEMS Microbiol Lett 29:63–67

    Article  CAS  Google Scholar 

  • Pieper DH, Stadler-Fritzsche K, Knackmuss H-J, Engesser KH, Bruce NC, Cain RB (1990) Purification and characterization of 4-methylmuconolactone methylisomerase, a novel enzyme of the modified 3-oxoadipate pathway in the Gram-negative bacterium Alcaligenes eutrophus JMP 134. Biochem J 271:529–534

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Pinyakong O, Habe H, Yoshida T, Nojiri H, Omori T (2003) Identification of three novel salicylate 1-hydroxylases involved in the phenanthrene degradation of Sphingobium sp strain P2. Biochem Biophys Res Commun 301:350–357

    Article  CAS  PubMed  Google Scholar 

  • Plaggenborg R, Steinbuchel A, Priefert H (2001) The coenzyme A-dependent, non-beta-oxidation pathway and not direct deacetylation is the major route for ferulic acid degradation in Delftia acidovorans. FEMS Microbiol Lett 205:9–16

    CAS  PubMed  Google Scholar 

  • Powell JA, Archer JA (1998) Molecular characterisation of a Rhodococcus ohp operon. Antonie Van Leeuwenhoek 74:175–188

    Article  CAS  PubMed  Google Scholar 

  • Powlowski J, Shingler V (1994) Genetics and biochemistry of phenol degradation by Pseudomonas sp. CF600. Biodegradation 5:219–236

    Article  CAS  PubMed  Google Scholar 

  • Powlowski J, Sealy J, Shingler V, Cadieux E (1997) On the role of DmpK, an auxiliary protein associated with multicomponent phenol hydroxylase from Pseudomonas sp. CF600. J Biol Chem 272:945–951

    Article  CAS  PubMed  Google Scholar 

  • Priefert H, Rabenhorst J, Steinbüchel A (2001) Biotechnological production of vanillin. Appl Microbiol Biotechnol 56:296–314

    Article  CAS  PubMed  Google Scholar 

  • Prucha M, Peterseim A, Pieper DH (1997) Evidence for an isomeric muconolactone isomerase involved in the metabolism of 4-methylmuconolactone by Alcaligenes eutrophus JMP134. Arch Microbiol 168:33–38

    Article  CAS  PubMed  Google Scholar 

  • Pujar BG, Ribbons DW (1985) Phthalate metabolism in Pseudomonas fluorescens PHK: purification and properties of 4,5-dihydroxyphthalate decarboxylase. Appl Environ Microbiol 49:374–376

    CAS  PubMed  PubMed Central  Google Scholar 

  • Ranjith NK, Sasikala C, Ramana Ch V (2007) Catabolism of L-phenylalanine and L-tyrosine by Rhodobacter sphaeroides OU5 occurs through 3,4-dihydroxyphenylalanine. Res Microbiol 158:506–511

    Article  CAS  PubMed  Google Scholar 

  • Reeve D, Carver MA, Hopper DJ (1989) The purification and characterization of 4-ethylphenol methylenehydroxylase, a flavocytochrome from Pseudomonas putida JD1. Biochem J 263:431–437

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Reineke W, Knackmuss H-J (1978) Chemical structure and biodegradability of halogenated aromatic compounds. Substituent effects on 1,2-dioxygenation of benzoic acid. Biochim Biophys Acta 532:412–423

    Article  Google Scholar 

  • Reiner AM (1972) Purification and properties of the catechol-forming enzyme 3,5-cyclohexadiene-1,2-diol-1-carboxylic acid (NAD+) oxidoreductase (decarboxylating). J Biol Chem 247:4960–4965

    CAS  PubMed  Google Scholar 

  • Reiner A, Hegeman G (1971) Metabolism of benzoic acid by bacteria. Accumulation of (−)-3,5-cyclohexadiene-1,2-diol-1-carboxylic acid by mutant strain of Alcaligenes eutrophus. Biochemistry 10:2530–2536

    Article  CAS  PubMed  Google Scholar 

  • Roper DI, Cooper RA (1990) Purification, some properties and nucleotide sequence of 5-carboxymethyl-2-hydroxymuconate isomerase of Escherichia coli C. Fed Eur Biochem Soc Lett 266:63–66

    Article  CAS  Google Scholar 

  • Sasoh M, Masai E, Ishibashi S, Hara H, Kamimura N, Miyauchi K, Fukuda M (2006) Characterization of the terephthalate degradation genes of Comamonas sp. strain E6. Appl Environ Microbiol 72:1825–1832

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Sauret-Ignazi G, Dardas A, Pelmont J (1988) Purification and properties of cytochrome P-450 from Moraxella sp. Biochimie 70:1385–1395

    Article  CAS  PubMed  Google Scholar 

  • Schläfli HR, Weiss MA, Leisinger T, Cook AM (1994) Terephthalate 1,2-dioxygenase system from Comamonas testosteroni T-2: purification and some properties of the oxygenase component. J Bacteriol 176:6644–6652

    Article  PubMed  PubMed Central  Google Scholar 

  • Schlömann M (1994) Evolution of chlorocatechol catabolic pathways. Biodegradation 5:301–321

    Article  PubMed  Google Scholar 

  • Schuhle K, Jahn M, Ghisla S, Fuchs G (2001) Two similar gene clusters coding for enzymes of a new type of aerobic 2-aminobenzoate (anthranilate) metabolism in the bacterium Azoarcus evansii. J Bacteriol 183:5268–5278

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Shen XH, Jiang CY, Huang Y, Liu ZP, Liu SJ (2005) Functional identification of novel genes involved in the glutathione-independent gentisate pathway in Corynebacterium glutamicum. Appl Environ Microbiol 71:3442–3452

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Shields MS, Montgomery SO, Chapman PJ, Cuskey SM, Pritchard PH (1989) Novel pathway of toluene catabolism in the trichloroethylene-degrading bacterium G4. Appl Environ Microbiol 55:1624–1629

    CAS  PubMed  PubMed Central  Google Scholar 

  • Shingler V, Powlowski J, Marklund U (1992) Nucleotide sequence and functional analysis of the complete phenol/3,4-dimethylphenol catabolic pathway of Pseudomonas sp. strain CF600. J Bacteriol 174:711–724

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Smith MA, Weaver VB, Young DM, Ornston LN (2003) Genes for chlorogenate and hydroxycinnamate catabolism (hca) are linked to functionally related genes in the dca-pca-qui-pob-hca chromosomal cluster of Acinetobacter sp strain ADP1. Appl Environ Microbiol 69:524–532

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Spence EL, Kawamukai M, Sanvoisin J, Braven H, Bugg TD (1996) Catechol dioxygenases from Escherichia coli (MhpB) and Alcaligenes eutrophus (MpcI): sequence analysis and biochemical properties of a third family of extradiol dioxygenases. J Bacteriol 178:5249–5256

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Suemori A, Kurane R, Tomizuka N (1993) Purification and properties of gentisate 1,2-dioxygenase from Rhodococcus erythropolis S-1. Biosci Biotechnol Biochem 57:1781–1783

    Article  CAS  Google Scholar 

  • Suemori A, Nakajima K, Kurane R, Nakamura Y (1996) Purification and characterization of o-hydroxyphenylacetate 5-hydroxylase, m-hydroxyphenylacetate 6-hydroxylase and p-hydroxyphenylacetate 1-hydroxylase from Rhodococcus erythropolis. J Ferment Bioeng 81:133–137

    Article  CAS  Google Scholar 

  • Sugimoto K, Senda T, Aoshima H, Masai E, Fukuda M, Mitsui Y (1999) Crystal structure of an aromatic ring opening dioxygenase LigAB, a protocatechuate 4,5-dioxygenase, under aerobic conditions. Structure 7:953–965

    Article  CAS  PubMed  Google Scholar 

  • Suske WA, Held M, Schmid A, Fleischmann T, Wubbolts MG, Kohler HPE (1997) Purification and characterization of 2-hydroxybiphenyl 3-monooxygenase, a novel NADH-dependent, FAD-containing aromatic hydroxylase from Pseudomonas azelaica HBP1. J Biol Chem 272:24257–24265

    Article  CAS  PubMed  Google Scholar 

  • Sutherland JB (1986) Demethylation of veratrole by cytochrome P-450 in Streptomyces setonii. Appl Environ Microbiol 52:98–100

    CAS  PubMed  PubMed Central  Google Scholar 

  • Tago K, Sato J, Takesa H, Kawagishi H, Hayatsu M (2005) Characterization of methylhydroquinone-metabolizing oxygenase genes encoded on plasmid in Burkholderia sp. NF100. J Biosci Bioeng 100:517–523

    Article  CAS  PubMed  Google Scholar 

  • Taguchi K, Motoyama M, Kudo T (2004) Multiplicity of 2,3-dihydroxybiphenyl dioxygenase genes in the Gram-positive polychlorinated biphenyl degrading bacterium Rhodococcus rhodochrous K37. Biosci Biotechnol Biochem 68:787–795

    Article  CAS  PubMed  Google Scholar 

  • Takenaka S, Murakami S, Shinke R, Hatakeyama K, Yukawa H, Aoki K (1997) Novel genes encoding 2-aminophenol 1,6-dioxygenase from Pseudomonas species AP-3 growing on 2-aminophenol and catalytic properties of the purified enzyme. J Biol Chem 272:14727–14732

    Article  CAS  PubMed  Google Scholar 

  • Takenaka S, Murakami S, Kim YJ, Aoki K (2000) Complete nucleotide sequence and functional analysis of the genes for 2-aminophenol metabolism from Pseudomonas sp. AP-3. Arch Microbiol 174:265–272

    Article  CAS  PubMed  Google Scholar 

  • Takenaka S, Asami T, Orii C, Murakami S, Aoki K (2002) A novel meta-cleavage dioxygenase that cleaves a carboxyl-group substituted 2-aminophenol – Purification and characterization of 4-amino-3-hydroxybenzoate 2,3-dioxygenase from Bordetella sp. strain 10d. Eur J Biochem 269:5871–5877

    Article  CAS  PubMed  Google Scholar 

  • Takenaka S, Okugawa S, Kadowaki M, Murakami S, Aoki K (2003) The metabolic pathway of 4-aminophenol in Burkholderia sp. strain AK-5 differs from that of aniline and aniline with C-4 substituents. Appl Environ Microbiol 69:5410–5413

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tao Y, Fishman A, Bentley WE, Wood TK (2004a) Altering toluene 4-monooxygenase by active-site engineering for the synthesis of 3-methoxycatechol, methoxyhydroquinone, and methylhydroquinone. J Bacteriol 186:4705–4713

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Tao Y, Fishman A, Bentley WE, Wood TK (2004b) Oxidation of benzene to phenol, catechol, and 1,2,3-trihydroxybenzene by toluene 4-monooxygenase of Pseudomonas mendocina KR1 and toluene 3-monooxygenase of Ralstonia pickettii PKO1. Appl Environ Microbiol 70:3814–3820

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Titus GP, Mueller HA, Burgner J, Rodríguez de Córdoba S, Peñalva MA, Timm DE (2000) Crystal structure of human homogentisate dioxygenase. Nat Struct Biol 7:542–546

    Article  CAS  PubMed  Google Scholar 

  • Vaillancourt FH, Labbe G, Drouin NM, Fortin PD, Eltis LD (2002) The mechanism-based inactivation of 2,3-dihydroxybiphenyl 1,2-dioxygenase by catecholic substrates. J Biol Chem 277:2019–2027

    Article  CAS  PubMed  Google Scholar 

  • Vaillancourt FH, Bolin JT, Eltis LD (2004) Ring-cleavage dioxygenases. In: Ramos JL (ed) Pseudomonas. Kluwer Academic/Plenum Publishers, New York, pp 359–395

    Chapter  Google Scholar 

  • Vaillancourt FH, Bolin JT, Eltis LD (2006) The ins and outs of ring-cleaving dioxygenases. Crit Rev Biochem Mol Biol 41:241–267

    Article  CAS  PubMed  Google Scholar 

  • van Berkel WJ, Kamerbeek NM, Fraaije MW (2006) Flavoprotein monooxygenases, a diverse class of oxidative biocatalysts. J Biotechnol 124:670–689

    Article  PubMed  CAS  Google Scholar 

  • Vardar G, Wood TK (2004) Protein engineering of toluene- o-xylene monooxygenase from Pseudomonas stutzeri OX1 for synthesizing 4-methylresorcinol, methylhydroquinone, and pyrogallol. Appl Environ Microbiol 70:3253–3262

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Vederas JC, Schleicher E, Tsai MD, Floss HG (1978) Stereochemistry and mechanism of reactions catalyzed by tryptophanase Escherichia coli. J Biol Chem 253:5350–5354

    CAS  PubMed  Google Scholar 

  • Vetting MW, Wackett LP, Que L, Lipscomb JD, Ohlendorf DH (2004) Crystallographic comparison of manganese- and iron-dependent homoprotocatechuate 2,3-dioxygenases. J Bacteriol 186:1945–1958

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wang L-H, Hamzah RY, Yu Y, Tu S-C (1987) Pseudomonas cepacia 3-hydroxybenzoate 6-hydroxylase: induction, purification, and characterization. Biochemistry 26:1099–1104

    Article  CAS  PubMed  Google Scholar 

  • Wang YZ, Zhou Y, Zylstra GJ (1995) Molecular analysis of isophthalate and terephthalate degradation by Comamonas testosteroni YZW-D. Environ Health Perspect 103(Suppl 5):9–12

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Whited GM, Gibson DT (1991) Toluene-4-monooxygenase, a three-component enzyme system that catalyzes the oxidation of toluene to p-cresol in Pseudomonas mendocina KR1. J Bacteriol 173:3010–3016

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Williams SE, Woodridge EM, Ransom SC, Landro JA, Babbitt PC, Kozarich JW (1992) 3-carboxy- cis, cis-muconate lactonizing enzymes from Pseudomonas putida is homologous to the class 2 fumarase family: a new reaction in the evolution of a mechanistic motif. Biochemistry 31:9768–9776

    Article  CAS  PubMed  Google Scholar 

  • Wolfe MD, Altier DJ, Stubna A, Popescu CV, Munck E, Lipscomb JD (2002) Benzoate 1,2-dioxygenase from Pseudomonas putida: single turnover kinetics and regulation of a two-component Rieske dioxygenase. Biochemistry 41:9611–9626

    Article  CAS  PubMed  Google Scholar 

  • Wolgel SA, Dege JE, Perkins-Olson PE, Juarez-Garcia CH, Crawford RL, Münck E, Lipscomb JD (1993) Purification and characterization of protocatechuate 2,3-dioxygenase from Bacillus macerans: a new extradiol catecholic dioxygenase. J Bacteriol 175:4414–4426

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Yamaguchi M, Fujisawa H (1980) Purification and characterization of an oxygenase component in benzoate 1,2-dioxygenase system from Pseudomonas arvilla C-1. J Biol Chem 255:5058–5063

    CAS  PubMed  Google Scholar 

  • Yamamoto S, Katagiri M, Maeno H, Hayaishi O (1965) Salicylate hydroxylase, a monooxygenase requiring flavin adenine dinucleotide. I. Purification and general properties. J Biol Chem 240:3408–3413

    CAS  PubMed  Google Scholar 

  • Yoshida R, Hori K, Fujiwara M, Saeki Y, Kagamiyama H (1976) Non-identical subunits of protocatechuate 3,4-dioxygenase. Biochemistry 15:4048–4053

    Article  CAS  PubMed  Google Scholar 

  • Yoshida T, Hayakawa Y, Matsui T, Nagasawa T (2004) Purification and characterization of 2,6-dihydroxybenzoate decarboxylase reversibly catalyzing nonoxidative decarboxylation. Arch Microbiol 181:391–397

    Article  CAS  PubMed  Google Scholar 

  • Zaar A, Gescher J, Eisenreich W, Bacher A, Fuchs G (2004) New enzymes involved in aerobic benzoate metabolism in Azoarcus evansii. Mol Microbiol 54:223–238

    Article  CAS  PubMed  Google Scholar 

  • Zhang Y, Colabroy KL, Begley TP, Ealick SE (2005) Structural studies on 3-hydroxyanthranilate-3,4-dioxygenase: the catalytic mechanism of a complex oxidation involved in NAD biosynthesis. Biochemistry 44:7632–7643

    Article  CAS  PubMed  Google Scholar 

  • Zhou NY, Al-Dulayymi J, Baird MS, Williams PA (2002) Salicylate 5-hydroxylase from Ralstonia sp. strain U2: a monooxygenase with close relationships to and shared electron transport proteins with naphthalene dioxygenase. J Bacteriol 184:1547–1555

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhuang Z, Song F, Takami H, Dunaway-Mariano D (2004) The BH1999 protein of Bacillus halodurans C-125 is gentisyl-coenzyme A thioesterase. J Bacteriol 186:393–399

    Article  CAS  PubMed  PubMed Central  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Dietmar H. Pieper .

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2019 Springer Nature Switzerland AG

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Pérez-Pantoja, D., González, B., Pieper, D.H. (2019). Aerobic Degradation of Aromatic Hydrocarbons. In: Rojo, F. (eds) Aerobic Utilization of Hydrocarbons, Oils, and Lipids. Handbook of Hydrocarbon and Lipid Microbiology . Springer, Cham. https://doi.org/10.1007/978-3-319-50418-6_10

Download citation

Publish with us

Policies and ethics