KEGG   PATHWAY: rn00361
Entry
rn00361                     Pathway                                

Name
Chlorocyclohexane and chlorobenzene degradation
Class
Metabolism; Xenobiotics biodegradation and metabolism
Pathway map
rn00361  Chlorocyclohexane and chlorobenzene degradation
rn00361

Module
M00547  Benzene/toluene degradation, benzene => catechol / toluene => 3-methylcatechol [PATH:rn00361]
M00548  Benzene degradation, benzene => catechol [PATH:rn00361]
Other DBs
UMBBD: hch ghch dcz 2,4-d pcp 2,4,5-t tcb
Reaction
R00812  cis-1,2-dihydrobenzene-1,2-diol:NAD+ oxidoreductase
R03543  benzene,NADH:oxygene 1,2-oxidoreductase
R03891  Benzene-1,2,4-triol:oxygen 1,2-oxidoreductase (decyclizing)
R03893  4-Carboxymethylenebut-2-en-4-olide lactonohydrolase
R03982  Pentachlorophenol,NADPH:oxygen oxidoreductase (hydroxylating, dechloronating)
R03997  2,4-dichlorophenol,NADPH:oxygen oxidoreductase(6-hydroxylating)
R04258   
R04259  (2R)-2-chloro-2,5-dihydro-5-oxofuran-2-acetate lyase (ring-opening)
R04500   
R04576  cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide cis-trans-isomerase
R05236  4-Hydroxymuconic-semialdehyde:NAD+ oxidoreductase
R05243  2,5-dichloro-2,5-cyclohexadiene-1,4-diol:NAD+ oxidoreductase
R05246   
R05267   
R05269   
R05287  Chloroacetic acid halidohydrolase
R05355   
R05369  1,3,4,6-tetrachloro-1,4-cyclohexadiene chlorohydrolase
R05370   
R05386  gamma-hexachlorocyclohexane chloride-lyase
R05387  gamma-pentachlorocyclohexene chloride-lyase
R05388  5-Chloro-1,2,4-trihydroxybenzene chloride-lyase
R05390   
R05392   
R05393   
R05397  3,6-dichloro-cis-1,2-dihydroxycyclohexa-3,5-diene:NAD+ oxidoreductase
R05399  NADH:2-hydroxy-1,4-benzoquinone oxidoreductase
R05402  glutathione disulfide:2,6-dichlorohydroquinone (chlorinating)
R05403  glutathione disulfide:2,6-dichlorohydroquinone (chlorinating)
R05406  catechol:oxygen 2,3-oxidoreductase (ring-opening)
R05407   
R05408   
R05409   
R05418   
R05419   
R05429  1,4-dichlorobenzene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
R05441  4-chlorophenol,NADPH:oxygen oxidoreductase (6-hydroxylating)
R05445   
R05446   
R05447   
R05448   
R05449  2,4,6-trichlorophenol,FADH2:oxygen oxidoreductase (dechlorinating)
R05483   
R05484   
R05493   
R05504   
R05505   
R05510  Protoanemonin lactonohydrolase
R05511   
R05533   
R05534   
R05535   
R05536   
R06831  1,2,4-trichlorobenzene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
R06832  3,4,6-trichloro-cis-1,2-dihydroxycyclohexa-3,5-diene:NAD+ oxidoreductase
R06833  catechol:oxygen 1,2-oxidoreductase
R06834  2-chloro-2,5-dihydro-5-oxofuran-2-acetate lyase
R06835  4-carboxymethylenebut-2-en-4-olide lactonohydrolase
R06838  4-carboxymethylenebut-2-en-4-olide lactonohydrolase
R06839  catechol:oxygen 1,2-oxidoreductase
R06840  2-chloro-2,5-dihydro-5-oxofuran-2-acetate lyase (decyclizing)
R06848  3-oxoadipate:NAD(P)+ oxidoreductase
R06849   
R06850   
R06851   
R06855   
R06856  chlorobenzene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
R06857  (1R,2R)-3-chlorocyclohexa-3,5-diene-1,2-diol:NAD+ oxidoreductase
R07669  beta-hexachlorocyclohexane halidohydrolase
R07670  beta-2,3,4,5,6-Pentachlorocyclohexanol halidohydrolase
R07793   
R07794   
R07827  3-chlorocatechol:oxygen 1,2-oxidoreductase (decyclizing)
R09130   
R09131   
R09132   
R09133   
R09134  tetrachlorocatechol:oxygen 1,2-oxidoreductase
R09135  2,3,5-trichlorodienelactone lyase (decyclizing)
R09136  2,3,5-trichlorodienelactone lactonohydrolase
R09137  2,4-dichloro-3-oxoadipate:NAD+ oxidoreductase
R09138  2,4-dichloro-3-oxoadipate:NADP+ oxidoreductase
R09139   
R10042  benzene,NADH:oxygen oxidoreductase
R10043  phenol,NADH:oxygen oxidoreductase (2-hydroxylating)
R11091   
R11092   
R11093   
R11585  2,3,5,6-tetrachlorohydroquinone:NAD+ oxidoreductase
Compound
C00011  CO2
C00042  Succinate
C00090  Catechol
C00146  Phenol
C00160  Glycolate
C00530  Hydroquinone
C00682  2-Hydroxymuconate semialdehyde
C01407  Benzene
C02124  4-Chlorophenol
C02222  2-Maleylacetate
C02375  4-Chlorocatechol
C02575  Pentachlorophenol
C02625  2,4-Dichlorophenol
C02814  Benzene-1,2,4-triol
C02933  3,5-Dichlorocatechol
C03434  Tetrachlorohydroquinone
C03572  2-Chloro-cis,cis-muconate
C03585  3-Chloro-cis,cis-muconate
C03664  2,4-Dichlorophenoxyacetate
C03918  2,4-Dichloro-cis,cis-muconate
C04091  cis-1,2-Dihydrobenzene-1,2-diol
C04431  cis-4-Carboxymethylenebut-2-en-4-olide
C04522  2-Chloro-2,5-dihydro-5-oxofuran-2-acetate
C04706  cis-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
C04729  trans-2-Chloro-4-carboxymethylenebut-2-en-1,4-olide
C05618  3-Chlorocatechol
C06328  6-Chlorobenzene-1,2,4-triol
C06329  2-Chloromaleylacetate
C06594  1,2,4-Trichlorobenzene
C06596  gamma-Pentachlorocyclohexene
C06597  1,3,4,6-Tetrachloro-1,4-cyclohexadiene
C06598  2,4,5-Trichloro-2,5-cyclohexadiene-1-ol
C06599  2,5-Dichloro-2,5-cyclohexadiene-1,4-diol
C06600  2,5-Dichlorohydroquinone
C06601  Chlorohydroquinone
C06602  2,5-Dichlorophenol
C06603  cis,cis-4-Hydroxymuconic semialdehyde
C06755  Chloroacetic acid
C06988  beta-1,2,3,4,5,6-Hexachlorocyclohexane
C06989  delta-3,4,5,6-Tetrachlorocyclohexene
C06990  Chlorobenzene
C07075  Lindane
C07088  4-Chlorophenoxyacetate
C07089  5-Chloro-2-hydroxymuconic semialdehyde
C07090  Protoanemonin
C07091  cis-Acetylacrylate
C07092  1,4-Dichlorobenzene
C07093  3,6-Dichloro-cis-1,2-dihydroxycyclohexa-3,5-diene
C07094  3,6-Dichlorocatechol
C07095  2,5-Dichloro-cis,cis-muconate
C07096  2,6-Dichlorophenol
C07097  2,6-Dichlorohydroquinone
C07098  2,4,6-Trichlorophenol
C07099  2,3,6-Trichlorohydroquinone
C07100  2,4,5-Trichlorophenoxyacetic acid
C07101  2,4,5-Trichlorophenol
C07102  5-Chloro-1,2,4-trihydroxybenzene
C07103  2-Hydroxy-1,4-benzoquinone
C11352  5,6-Dichloro-1,3-cyclohexadiene
C12831  3,4,6-Trichlorocatechol
C12832  3,4,6-Trichloro-cis-1,2-dihydroxycyclohexa-3,5-diene
C12833  2,3,5-Trichloro-cis,cis-muconate
C12834  2,5-Dichloro-carboxymethylenebut-2-en-4-olide
C12835  2,5-Dichloro-4-oxohex-2-enedioate
C12836  2-Chloro-3-oxoadipate
C12837  3-Chloro-cis-1,2-dihydroxycyclohexa-3,5-diene
C12838  trans-4-Carboxymethylenebut-2-en-4-olide
C14419  2,4-Dichloroaniline
C14450  4-Chloroaniline
C16181  beta-2,3,4,5,6-Pentachlorocyclohexanol
C16182  beta-2,3,5,6-Tetrachloro-1,4-cyclohexanediol
C16266  3-Chloro-2-hydroxymuconic semialdehyde
C18236  1,2,3,4-Tetrachlorobenzene
C18238  cis-Chlorobenzene dihydrodiol
C18240  Tetrachlorocatechol
C18241  Tetrachloro-cis,cis-muconate
C18242  2,3,5-Trichlorodienelactone
C18243  2,3,5-Trichloromaleylacetate
C18244  2,4-Dichloro-3-oxoadipate
C18933  Chloranil
C21103  2,6-Dichloro-p-benzoquinone
C21104  2,5-Dichloro-p-benzoquinone
C21105  5-Chloro-2-hydroxy-p-benzoquinone
Reference
  Authors
Xun L, Bohuslavek J, Cai M.
  Title
Characterization of 2,6-dichloro-p-hydroquinone 1,2-dioxygenase (PcpA) of Sphingomonas chlorophenolica ATCC 39723.
  Journal
Biochem Biophys Res Commun 266:322-5 (1999)
DOI:10.1006/bbrc.1999.1805
Reference
PMID:1987135
  Authors
van der Meer JR, van Neerven AR, de Vries EJ, de Vos WM, Zehnder AJ.
  Title
Cloning and characterization of plasmid-encoded genes for the degradation of 1,2-dichloro-, 1,4-dichloro-, and 1,2,4-trichlorobenzene of Pseudomonas sp. strain P51.
  Journal
J Bacteriol 173:6-15 (1991)
DOI:10.1128/jb.173.1.6-15.1991
Reference
  Authors
Nagata Y, Futamura A, Miyauchi K, Takagi M.
  Title
Two different types of dehalogenases, LinA and LinB, involved in gamma-hexachlorocyclohexane degradation in Sphingomonas paucimobilis UT26 are localized in the periplasmic space without molecular processing.
  Journal
J Bacteriol 181:5409-13 (1999)
DOI:10.1128/JB.181.17.5409-5413.1999
Reference
  Authors
Nagata Y, Miyauchi K, Takagi M.
  Title
Complete analysis of genes and enzymes for gamma-hexachlorocyclohexane degradation in Sphingomonas paucimobilis UT26.
  Journal
J Ind Microbiol Biotechnol 23:380-390 (1999)
DOI:10.1038/sj/jim/2900736
Reference
  Authors
Dogra C, Raina V, Pal R, Suar M, Lal S, Gartemann KH, Holliger C, van der Meer JR, Lal R.
  Title
Organization of lin genes and IS6100 among different strains of hexachlorocyclohexane-degrading Sphingomonas paucimobilis: evidence for horizontal gene transfer.
  Journal
J Bacteriol 186:2225-35 (2004)
DOI:10.1128/JB.186.8.2225-2235.2004
Reference
  Authors
Nagata Y, Prokop Z, Marvanova S, Sykorova J, Monincova M, Tsuda M, Damborsky J.
  Title
Reconstruction of mycobacterial dehalogenase Rv2579 by cumulative mutagenesis of haloalkane dehalogenase LinB.
  Journal
Appl Environ Microbiol 69:2349-55 (2003)
DOI:10.1128/AEM.69.4.2349-2355.2003
Reference
  Authors
Vedler E, Vahter M, Heinaru A.
  Title
The completely sequenced plasmid pEST4011 contains a novel IncP1 backbone and a catabolic transposon harboring tfd genes for 2,4-dichlorophenoxyacetic acid degradation.
  Journal
J Bacteriol 186:7161-74 (2004)
DOI:10.1128/JB.186.21.7161-7174.2004
Reference
PMID:9148781
  Authors
Sommer C, Gorisch H.
  Title
Enzymology of the degradation of (di)chlorobenzenes by Xanthobacter flavus 14p1.
  Journal
Arch Microbiol 167:384-91 (1997)
DOI:10.1007/s002030050459
Reference
  Authors
Laemmli CM, Schonenberger R, Suter M, Zehnder AJ, van der Meer JR.
  Title
TfdD(II), one of the two chloromuconate cycloisomerases of Ralstonia eutropha JMP134 (pJP4), cannot efficiently convert 2-chloro- cis, cis-muconate to trans-dienelactone to allow growth on 3-chlorobenzoate.
  Journal
Arch Microbiol 178:13-25 (2002)
DOI:10.1007/s00203-002-0417-3
Reference
  Authors
Wu J, Hong Q, Han P, He J, Li S.
  Title
A gene linB2 responsible for the conversion of beta-HCH and 2,3,4,5,6-pentachlorocyclohexanol in Sphingomonas sp. BHC-A.
  Journal
Appl Microbiol Biotechnol 73:1097-105 (2007)
DOI:10.1007/s00253-006-0579-z
Reference
PMID:9758802
  Authors
Potrawfke T, Timmis KN, Wittich RM
  Title
Degradation of 1,2,3,4-tetrachlorobenzene by pseudomonas chlororaphis RW71
  Journal
Appl Environ Microbiol 64:3798-806 (1998)
DOI:10.1128/AEM.64.10.3798-3806.1998
Reference
  Authors
Potrawfke T, Armengaud J, Wittich RM
  Title
Chlorocatechols substituted at positions 4 and 5 are substrates of the broad-spectrum chlorocatechol 1,2-dioxygenase of Pseudomonas chlororaphis RW71.
  Journal
J Bacteriol 183:997-1011 (2001)
DOI:10.1128/JB.183.3.997-1011.2001
Related
pathway
rn00020  Citrate cycle (TCA cycle)
rn00362  Benzoate degradation
rn00630  Glyoxylate and dicarboxylate metabolism
KO pathway
ko00361   

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