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(+)-2-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
(+)-5-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
2,4-dichloro-cis,cis-muconate
2-chlorodienelactone
-
-
-
-
?
2,4-dichloro-cis,cis-muconate
?
2,5-Dichloro-cis,cis-muconate
?
-
-
-
-
?
2-chloro-3-methylmuconate
5-chloro-4-methylmuconolactone + 2-chloro-3-methylmuconolactone
2-chloro-4-methylmuconate
5-chloro-3-methylmuconolactone + 2-chloro-4-methylmuconolactone
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
2-Methyl-cis,cis-muconate
?
3-Bromo-cis,cis-muconate
5-bromomuconolactone
3-chloro-2-methylmuconate
5-methyl-cis-dienelactone + 2-chloro-3-methylmuconolactone
3-chloro-2-methylmuconolactone + 3-chloro-2-methylmuconolactone
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
3-Fluoro-cis,cis-muconate
?
-
-
-
-
?
3-Methyl-cis,cis-muconate
?
4-chloro-2-methylmuconate
2-methyl-cis-dienelactone + 3-chloro-5-methylmuconolactone
additional information
?
-
(+)-2-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
-
-
-
?
(+)-2-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
-
-
-
?
(+)-5-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
-
-
-
?
(+)-5-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
-
-
-
?
(+)-5-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
-
elimination of chloride is not catalyzed
-
-
?
2,4-dichloro-cis,cis-muconate
?
-
-
-
-
?
2,4-dichloro-cis,cis-muconate
?
-
-
-
-
?
2,4-dichloro-cis,cis-muconate
?
-
-
-
-
?
2,4-dichloro-cis,cis-muconate
?
-
-
-
-
?
2-chloro-3-methylmuconate
5-chloro-4-methylmuconolactone + 2-chloro-3-methylmuconolactone
-
-
-
-
?
2-chloro-3-methylmuconate
5-chloro-4-methylmuconolactone + 2-chloro-3-methylmuconolactone
-
-
-
-
?
2-chloro-4-methylmuconate
5-chloro-3-methylmuconolactone + 2-chloro-4-methylmuconolactone
-
-
-
-
?
2-chloro-4-methylmuconate
5-chloro-3-methylmuconolactone + 2-chloro-4-methylmuconolactone
-
-
-
-
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
-
trans-4-carboxymethylenebut-2-en-4-olide is produced after dehalogenation
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
-
trans-4-carboxymethylenebut-2-en-4-olide is produced after dehalogenation
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
-
-
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
65% of the activity relative to 2-methyl-cis,cis-muconate
trans-4-carboxymethylenebut-2-en-4-olide is produced after dehalogenation
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
-
-
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
-
-
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
-
-
-
-
?
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
r
the enzyme is unable to catalyze dehalogenation
?
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
-
-
?
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
-
-
?
2-Methyl-cis,cis-muconate
?
-
-
-
-
?
2-Methyl-cis,cis-muconate
?
-
-
-
-
?
2-Methyl-cis,cis-muconate
?
-
most effective substrate
-
-
?
2-Methyl-cis,cis-muconate
?
-
-
-
-
?
2-Methyl-cis,cis-muconate
?
-
-
-
-
?
3-Bromo-cis,cis-muconate
5-bromomuconolactone
-
-
-
?
3-Bromo-cis,cis-muconate
5-bromomuconolactone
-
-
-
?
3-chloro-2-methylmuconate
5-methyl-cis-dienelactone + 2-chloro-3-methylmuconolactone
-
-
-
-
?
3-chloro-2-methylmuconate
5-methyl-cis-dienelactone + 2-chloro-3-methylmuconolactone
-
-
-
-
?
3-chloro-2-methylmuconolactone + 3-chloro-2-methylmuconolactone
?
-
-
-
-
?
3-chloro-2-methylmuconolactone + 3-chloro-2-methylmuconolactone
?
-
-
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
about 90% of the activity compared to 2-methyl-cis,cis-muconate
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
about 90% of the activity compared to 2-methyl-cis,cis-muconate
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
corresponding (E)-dienenlactone
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
73% of the activity relative to 2-methyl-cis,cis-muconate
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
corresponding (E)-dienenlactone
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
-
-
-
-
?
3-Methyl-cis,cis-muconate
?
-
84% of the activity relative to 2-methyl-cis,cis-muconate
-
-
?
3-Methyl-cis,cis-muconate
?
-
-
-
-
?
3-Methyl-cis,cis-muconate
?
-
-
-
?
3-Methyl-cis,cis-muconate
?
-
-
-
-
?
4-chloro-2-methylmuconate
2-methyl-cis-dienelactone + 3-chloro-5-methylmuconolactone
-
-
-
-
?
4-chloro-2-methylmuconate
2-methyl-cis-dienelactone + 3-chloro-5-methylmuconolactone
-
-
-
-
?
cis,cis-Muconate
?
-
-
-
-
?
cis,cis-Muconate
?
-
about 30% of the activity compared to 2-methyl-cis,cis-muconate
-
-
?
cis,cis-Muconate
?
-
about 30% of the activity compared to 2-methyl-cis,cis-muconate
-
-
?
cis,cis-Muconate
?
-
36% of the activity relative to 2-methyl-cis,cis-muconate
-
-
?
cis,cis-Muconate
?
-
-
-
-
?
cis,cis-Muconate
?
-
-
-
?
cis,cis-Muconate
?
-
-
-
-
?
additional information
?
-
-
completely inactive with 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
completely inactive with 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
induced at low levels in strain RD330 by 3-chlorobenzoate and its metabolites
-
-
?
additional information
?
-
-
enzyme is involved in the 2,4-dichlorophenoxyacetate degradation pathway
-
-
?
additional information
?
-
-
induced at low levels in strain RD330 by 3-chlorobenzoate and its metabolites
-
-
?
additional information
?
-
-
completely inactive with 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
the enzyme is involved in the degradation of 3,5-dichlorocatechol
-
-
?
additional information
?
-
-
the enzyme is involved in the degradation of 3,5-dichlorocatechol
-
-
?
additional information
?
-
-
completely inactive with 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
completely inactive with 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
no activity with cis,cis-muconate, 3-chloromuconate, 3-methylmuconate and 2,4-dichloromuconate
-
?
additional information
?
-
-
key enzyme in a modified ortho-pathway in cells utilizing 2-chlorophenol via a 3-chlorocatechol branch of a modified ortho-pathway
-
?
additional information
?
-
-
no activity with cis,cis-muconate, 3-chloromuconate, 3-methylmuconate and 2,4-dichloromuconate
-
?
additional information
?
-
-
key enzyme in a modified ortho-pathway in cells utilizing 2-chlorophenol via a 3-chlorocatechol branch of a modified ortho-pathway
-
?
additional information
?
-
-
rate-limiting step in the conversion of dichloromuconate to chloromaleylacetate
-
-
?
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0.274 - 0.819
(+)-2-Chloromuconolactone
0.805
(+)-5-chloromuconolactone
-
-
0.0182 - 0.119
2,4-dichloro-cis,cis-muconate
0.0559 - 0.312
2-chloro-cis,cis-muconate
0.0309 - 0.065
2-methyl-cis,cis-muconate
0.05 - 1.24
3-chloro-cis,cis-muconate
0.052
3-fluoro-cis,cis-muconate
-
-
0.0134 - 0.066
3-methyl-cis,cis-muconate
0.0813 - 6.997
cis,cis-muconate
0.274
(+)-2-Chloromuconolactone
-
measurement of substrate consumption
0.819
(+)-2-Chloromuconolactone
-
measurement of product formation
0.0182
2,4-dichloro-cis,cis-muconate
-
-
0.119
2,4-dichloro-cis,cis-muconate
-
-
0.0559
2-chloro-cis,cis-muconate
pH and temperature not specified in the publication
0.0601
2-chloro-cis,cis-muconate
-
-
0.0781
2-chloro-cis,cis-muconate
-
measurement of substrate consumption
0.1429
2-chloro-cis,cis-muconate
-
-
0.287
2-chloro-cis,cis-muconate
-
measurement of product formation
0.312
2-chloro-cis,cis-muconate
-
-
0.0309
2-methyl-cis,cis-muconate
-
-
0.047
2-methyl-cis,cis-muconate
-
-
0.065
2-methyl-cis,cis-muconate
-
-
0.05
3-chloro-cis,cis-muconate
-
-
0.1286
3-chloro-cis,cis-muconate
-
-
0.173
3-chloro-cis,cis-muconate
-
-
1.24
3-chloro-cis,cis-muconate
pH and temperature not specified in the publication
0.0134
3-methyl-cis,cis-muconate
-
-
0.0487
3-methyl-cis,cis-muconate
pH and temperature not specified in the publication
0.066
3-methyl-cis,cis-muconate
-
-
0.0813
cis,cis-muconate
pH and temperature not specified in the publication
0.083
cis,cis-muconate
-
-
0.0928
cis,cis-muconate
-
-
0.0928
cis,cis-muconate
-
3-chloro-cis,cis-muconate
6.997
cis,cis-muconate
-
-
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2.12 - 3.95
(+)-2-Chloromuconolactone
24.7
(+)-5-chloromuconolactone
-
-
22.3 - 44.7
2,4-dichloro-cis,cis-muconate
2.2 - 171000
2-chloro-cis,cis-muconate
0.0567
2-methyl-cis,cis-muconate
-
-
8.8 - 60.7
3-chloro-cis,cis-muconate
6.07
3-fluoro-cis,cis-muconate
-
-
0.8 - 3.2
3-methyl-cis,cis-muconate
4.33 - 24.66
cis,cis-muconate
additional information
additional information
-
-
-
2.12
(+)-2-Chloromuconolactone
-
measurement of substrate consumption
3.95
(+)-2-Chloromuconolactone
-
measurement of product formation
22.3
2,4-dichloro-cis,cis-muconate
-
-
44.7
2,4-dichloro-cis,cis-muconate
-
-
2.2
2-chloro-cis,cis-muconate
-
-
3.6
2-chloro-cis,cis-muconate
pH and temperature not specified in the publication
3.83
2-chloro-cis,cis-muconate
-
measurement of substrate consumption
10.3
2-chloro-cis,cis-muconate
-
measurement of product formation
171000
2-chloro-cis,cis-muconate
-
-
8.8
3-chloro-cis,cis-muconate
pH and temperature not specified in the publication
57.7
3-chloro-cis,cis-muconate
-
-
60.7
3-chloro-cis,cis-muconate
-
-
0.8
3-methyl-cis,cis-muconate
-
-
3.2
3-methyl-cis,cis-muconate
pH and temperature not specified in the publication
4.33
cis,cis-muconate
-
-
24.66
cis,cis-muconate
pH and temperature not specified in the publication
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Schmidt, E.; Knackmuss, H.J.
Chemical structure and biodegradability of halogenated aromatic compounds. Conversion of chlorinated muconic acids into maleoylacetic acid
Biochem. J.
192
339-347
1980
Pseudomonas sp.
brenda
Mazur, P.; Piecken, W.A.; Budihas, S.R.; Williams, S.E.; Wong, S.; Kozarich, J.W.
cis,cis-Muconate lactonizing enzyme from Trichosporon cutaneum: evidence for a novel class of cycloisomerases in eucaryotes
Biochemistry
33
1961-1970
1994
Pseudomonas sp., Pseudomonas sp. B13
brenda
Hinteregger, C.; Ferschl, A.; Loidl, M.; Streichsbier, F.
Metabolism of aniline and 3-chloroaniline in Pseudomonas acidovorans CA28: evidence of isofunctional muconate cycloisomerases
J. Basic Microbiol.
33
301-309
1993
Delftia acidovorans
-
brenda
Solyanikova, I.P.; Maltseva, O.V.; Vollmer, M.D.; Golovleva, L.A.; Schlmann, M.
Characterization of muconate and chloromuconate cycloisomerase from Rhodococcus erythropolis 1CP: indications for functionally convergent evolution among bacterial cycloisomerases
J. Bacteriol.
177
2821-2826
1995
Rhodococcus erythropolis, Rhodococcus erythropolis 1CP
brenda
Schmidt, E.; Remberg, G.; Knackmuss, H.J.
Chemical structure and biodegradability of halogenated aromatic compounds. Halogenated muconic acids as intermediates
Biochem. J.
192
331-337
1980
Pseudomonas sp., Pseudomonas sp. B13
brenda
Don, R.H.; Weightman, A.J.; Knackmuss, H.J.; Timmis, K.N.
Transposon mutagenesis and cloning analysis of the pathways for degradation of 2,4-dichlorophenoxyacetic acid and 3-chlorobenzoate in Alcaligenes eutrophus JMP134(pJP4)
J. Bacteriol.
161
85-90
1985
Cupriavidus necator, Cupriavidus necator JMP134(pJP4)
brenda
Schmidt, E.
Bioconversion of 3-chlorobenzoate to 2-chloromuconate controlled by on line HPLC
Appl. Microbiol. Biotechnol.
27
347-350
1988
Cupriavidus necator, Cupriavidus necator RD330
-
brenda
Ngai, K.L.; Ornston, L.N.
Abundant expression of pseudomonas genes for chlorocatechol metabolism
J. Bacteriol.
170
2412-2413
1988
Pseudomonas sp.
brenda
Schmidt, E.; Knackmuss, H.J.
Production of cis,cis-muconate from benzoate and 2-fluoro-cis,cis-muconate from 3-fluorobenzoate by 3-chlorobenzoate degrading bacteria
Appl. Microbiol. Biotechnol.
20
351-355
1984
Alcaligenes sp., Pseudomonas sp., Pseudomonas sp. B13, Alcaligenes sp. A7-2
-
brenda
Schwien, U.; Schmidt, E.; Knackmuss, H.J.; Reineke, W.
Degradation of chlorosubstituted aromatic compounds by pseudomonas sp. Strain B13: fate of 3,5-dichlorocatechol
Arch. Microbiol.
150
78-84
1988
Pseudomonas sp., Pseudomonas sp. B13
-
brenda
Kleywegt, G.J.; Hoier, H.; Jones, T.A.
A re-evaluation of the crystal structure of chloromuconate cycloisomerase
Acta Crystallogr. Sect. D
52
858-863
1996
Cupriavidus necator
brenda
Hoier, H.; Schlmann, M.; Hammer, A.; Glusker, J.P.; Carrell, H.L.; Goldman, A.; Stezowski, J.J.; Heinemann, U.
Crystal structure of chloromuconate cycloisomerase from Alcaligenes eutrophus JMP134(pJP4) at 3 A resolution
Acta Crystallogr. Sect. D
50
75-84
1994
Cupriavidus necator
brenda
Sommer, C.; Grisch, H.
Enzymology of the degradation of (di)chlorobenzenes by Xanthomonas flavus 14p1
Arch. Microbiol.
167
384-391
1997
Xanthobacter flavus
brenda
Vollmer, M.D.; Schlmann, M.
Conversion of 2-chloro-cis,cis-muconate and its metabolites 2-chloro- and 5-chloromuconolactone by chloromuconate cycloisomerases of pJP4 and pAC27
J. Bacteriol.
177
2938-2941
1995
Cupriavidus necator, Escherichia coli
brenda
Eulberg, D.; Kourbatova, E.M.; Golovleva, L.A.; Schlmann, M.
Evolutionary relationship between chlorocatechol catabolic enzymes from Rhodococcus opacus 1CP and their counterparts in proteobacteria: sequence divergence and functional convergence
J. Bacteriol.
180
1082-1094
1998
Rhodococcus opacus
brenda
Moiseeva, O.V.; Belova, O.V.; Solyanikova, I.P.; Schlomann, M.; Golovleva, L.A.
Enzymes of a new modified ortho-pathway utilizing 2-chlorophenol in Rhodococcus opacus 1CP
Biochemistry (Moscow)
66
548-555
2001
Rhodococcus opacus, Rhodococcus opacus 1CP
brenda
Pollmann, K.; Wray, V.; Pieper, D.H.
Chloromethylmuconolactones as critical metabolites in the degradation of chloromethylcatechols: recalcitrance of 2-chlorotoluene
J. Bacteriol.
187
2332-2340
2005
Ralstonia sp., Ralstonia sp. PS12
brenda
Kolomytseva, M.; Ferraroni, M.; Chernykh, A.; Golovleva, L.; Scozzafava, A.
Structural basis for the substrate specificity and the absence of dehalogenation activity in 2-chloromuconate cycloisomerase from Rhodococcus opacus 1CP
Biochim. Biophys. Acta
1844
1541-1549
2014
Rhodococcus opacus (Q8G9L1)
brenda
Kumar, A.; Trefault, N.; Olaniran, A.O.
Microbial degradation of 2,4-dichlorophenoxyacetic acid Insight into the enzymes and catabolic genes involved, their regulation and biotechnological implications
Crit. Rev. Microbiol.
42
194-208
2016
Cupriavidus necator
brenda