Information on EC 5.5.1.7 - Chloromuconate cycloisomerase

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The expected taxonomic range for this enzyme is: Bacteria

EC NUMBER
COMMENTARY
5.5.1.7
-
RECOMMENDED NAME
GeneOntology No.
Chloromuconate cycloisomerase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
2-chloro-2,5-dihydro-5-oxofuran-2-acetate = 3-chloro-cis,cis-muconate
show the reaction diagram
syn cycloisomerization
-
2-chloro-2,5-dihydro-5-oxofuran-2-acetate = 3-chloro-cis,cis-muconate
show the reaction diagram
syn cycloisomerization
Pseudomonas sp. B13
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,4-dichlorotoluene degradation
-
-
3-chlorocatechol degradation
-
-
4-chlorocatechol degradation
-
-
4-methylcatechol degradation (ortho cleavage)
-
-
Chlorocyclohexane and chlorobenzene degradation
-
-
chlorosalicylate degradation
-
-
Fluorobenzoate degradation
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
Toluene degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
2-chloro-2,5-dihydro-5-oxofuran-2-acetate lyase (decyclizing)
Requires Mn2+. The product of cycloisomerization of 3-chloro-cis,cis-muconate spontaneously eliminates chloride to produce cis-4-carboxymethylenebut-2-en-4-olide. Also acts (in the reverse direction) on 2-chloro-cis,cis-muconate. Not identical with EC 5.5.1.1 (muconate cycloisomerase) or EC 5.5.1.11 (dichloromuconate cycloisomerase).
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
2-chloro-5-oxo-2,5-dihydrofuran-2-acetate lyase (decyclizing)
-
-
-
-
2CMA-cycloisomerase
-
-
-
-
CMC
-
-
-
-
Isomerase, chloromuconate cyclo-
-
-
-
-
MLE II
-
-
-
-
Muconate cycloisomerase II
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
95990-33-3
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain A7-2
-
-
Manually annotated by BRENDA team
Alcaligenes sp. A7-2
strain A7-2
-
-
Manually annotated by BRENDA team
basonym Alcaligenes eutrophus
-
-
Manually annotated by BRENDA team
basonym Alcaligenes eutrophus; JMP134(pJP4)
-
-
Manually annotated by BRENDA team
basonym Alcaligenes eutrophus; JMP134, pJP4-encoded enzyme
-
-
Manually annotated by BRENDA team
basonym Alcaligenes eutrophus; strain RD330 a transposon mutant of JMP134
-
-
Manually annotated by BRENDA team
Cupriavidus necator JMP134(pJP4)
JMP134(pJP4)
-
-
Manually annotated by BRENDA team
Cupriavidus necator RD330
strain RD330 a transposon mutant of JMP134
-
-
Manually annotated by BRENDA team
DH1(pDC100), pAC27-encoded enzyme
-
-
Manually annotated by BRENDA team
Pseudomonas sp. B13
B13
-
-
Manually annotated by BRENDA team
strain PS12
-
-
Manually annotated by BRENDA team
Ralstonia sp. PS12
strain PS12
-
-
Manually annotated by BRENDA team
Rhodococcus erythropolis 1CP
1CP
-
-
Manually annotated by BRENDA team
strain1CP
-
-
Manually annotated by BRENDA team
Rhodococcus opacus strain1CP
strain1CP
-
-
Manually annotated by BRENDA team
Xanthobacter flavus 14p1
14p1
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(+)-2-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
show the reaction diagram
-
-
-
-
(+)-5-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
show the reaction diagram
-
-
-
-
(+)-5-Chloromuconolactone
trans-4-Carboxymethylenebut-2-en-4-olide + Cl-
show the reaction diagram
-
elimination of chloride is not catalyzed
-
-
-
2,4-Dichloro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2,4-Dichloro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2,4-Dichloro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2,5-Dichloro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2-chloro-3-methylmuconate
5-chloro-4-methylmuconolactone + 2-chloro-3-methylmuconolactone
show the reaction diagram
Ralstonia sp., Ralstonia sp. PS12
-
-
-
-
?
2-chloro-4-methylmuconate
5-chloro-3-methylmuconolactone + 2-chloro-4-methylmuconolactone
show the reaction diagram
Ralstonia sp., Ralstonia sp. PS12
-
-
-
-
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
show the reaction diagram
-
-
-
-
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
show the reaction diagram
-
-
-
-
-
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
show the reaction diagram
Q8G9L1
-
-
-
?
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
show the reaction diagram
-
-
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
show the reaction diagram
-
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
show the reaction diagram
Pseudomonas sp. B13
-
-
-
-
2-Chloro-cis,cis-muconate
4-Carboxymethyl-2-chloro-but-2-en-4-olide
show the reaction diagram
Xanthobacter flavus 14p1
-
-
-
-
-
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
show the reaction diagram
-
-
-
?
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
show the reaction diagram
-
r
the enzyme is unable to catalyze dehalogenation
-
2-Chloro-cis,cis-muconate
5-Chloromuconolactone
show the reaction diagram
Rhodococcus opacus strain1CP
-
-
-
?
2-Methyl-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2-Methyl-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2-Methyl-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
2-Methyl-cis,cis-muconate
?
show the reaction diagram
-
most effective substrate
-
-
-
2-Methyl-cis,cis-muconate
?
show the reaction diagram
Delftia acidovorans CA28
-
-
-
-
-
2-Methyl-cis,cis-muconate
?
show the reaction diagram
Xanthobacter flavus 14p1
-
-
-
-
-
3-Bromo-cis,cis-muconate
Corresponding (E)-dienelactone
show the reaction diagram
Pseudomonas sp., Pseudomonas sp. B13
-
-
-
-
3-chloro-2-methylmuconate
5-methyl-cis-dienelactone + 2-chloro-3-methylmuconolactone
show the reaction diagram
Ralstonia sp., Ralstonia sp. PS12
-
-
-
-
?
3-chloro-2-methylmuconolactone + 3-chloro-2-methylmuconolactone
?
show the reaction diagram
Ralstonia sp., Ralstonia sp. PS12
-
-
-
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
-
-
-
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
-
-
-
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
-
-
-
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
Q8G9L1
-
-
-
?
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
-
-
corresponding (E)-dienenlactone
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
-
73% of the activity relative to 2-methyl-cis,cis-muconate
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
-
about 90% of the activity compared to 2-methyl-cis,cis-muconate
-
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
Pseudomonas sp. B13
-
-
corresponding (E)-dienenlactone
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
Delftia acidovorans CA28
-
about 90% of the activity compared to 2-methyl-cis,cis-muconate
-
-
-
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
Xanthobacter flavus 14p1
-
-
-
-
-
3-Fluoro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
3-Methyl-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
3-Methyl-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
3-Methyl-cis,cis-muconate
?
show the reaction diagram
Q8G9L1
-
-
-
?
3-Methyl-cis,cis-muconate
?
show the reaction diagram
-
84% of the activity relative to 2-methyl-cis,cis-muconate
-
-
-
3-Methyl-cis,cis-muconate
?
show the reaction diagram
Xanthobacter flavus 14p1
-
-
-
-
-
4-chloro-2-methylmuconate
2-methyl-cis-dienelactone + 3-chloro-5-methylmuconolactone
show the reaction diagram
Ralstonia sp., Ralstonia sp. PS12
-
-
-
-
?
cis,cis-Muconate
?
show the reaction diagram
-
-
-
-
-
cis,cis-Muconate
?
show the reaction diagram
-
-
-
-
-
cis,cis-Muconate
?
show the reaction diagram
-
-
-
-
-
cis,cis-Muconate
?
show the reaction diagram
Q8G9L1
-
-
-
?
cis,cis-Muconate
?
show the reaction diagram
-
about 30% of the activity compared to 2-methyl-cis,cis-muconate
-
-
-
cis,cis-Muconate
?
show the reaction diagram
-
36% of the activity relative to 2-methyl-cis,cis-muconate
-
-
-
cis,cis-Muconate
?
show the reaction diagram
Delftia acidovorans CA28
-
about 30% of the activity compared to 2-methyl-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
?
-
-
no activity with cis,cis-muconate, 3-chloromuconate, 3-methylmuconate and 2,4-dichloromuconate
-
?
additional information
?
-
-
the enzyme is involved in the degradation of 3,5-dichlorocatechol
-
-
-
additional information
?
-
-
rate-limiting step in the conversion of dichloromuconate to chloromaleylacetate
-
-
-
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
?
-
-
key enzyme in a modified ortho-pathway in cells utilizing 2-chlorophenol via a 3-chlorocatechol branch of a modified ortho-pathway
-
?
additional information
?
-
Pseudomonas sp. B13
-
the enzyme is involved in the degradation of 3,5-dichlorocatechol
-
-
-
additional information
?
-
Pseudomonas sp. B13, Alcaligenes sp. A7-2
-
completely inactive with 2-fluoro-cis,cis-muconate
-
-
-
additional information
?
-
Rhodococcus opacus strain1CP
-
no activity with cis,cis-muconate, 3-chloromuconate, 3-methylmuconate and 2,4-dichloromuconate, key enzyme in a modified ortho-pathway in cells utilizing 2-chlorophenol via a 3-chlorocatechol branch of a modified ortho-pathway
-
?
additional information
?
-
Xanthobacter flavus 14p1
-
rate-limiting step in the conversion of dichloromuconate to chloromaleylacetate
-
-
-
additional information
?
-
Cupriavidus necator RD330
-
induced at low levels in strain RD330 by 3-chlorobenzoate and its metabolites
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
the enzyme is involved in the degradation of 3,5-dichlorocatechol
-
-
-
additional information
?
-
-
rate-limiting step in the conversion of dichloromuconate to chloromaleylacetate
-
-
-
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
?
-
-
key enzyme in a modified ortho-pathway in cells utilizing 2-chlorophenol via a 3-chlorocatechol branch of a modified ortho-pathway
-
?
additional information
?
-
Pseudomonas sp. B13
-
the enzyme is involved in the degradation of 3,5-dichlorocatechol
-
-
-
additional information
?
-
Rhodococcus opacus strain1CP
-
key enzyme in a modified ortho-pathway in cells utilizing 2-chlorophenol via a 3-chlorocatechol branch of a modified ortho-pathway
-
?
additional information
?
-
Xanthobacter flavus 14p1
-
rate-limiting step in the conversion of dichloromuconate to chloromaleylacetate
-
-
-
additional information
?
-
Cupriavidus necator RD330
-
induced at low levels in strain RD330 by 3-chlorobenzoate and its metabolites
-
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.274
(+)-2-Chloromuconolactone
-
measurement of substrate consumption
0.819
(+)-2-Chloromuconolactone
-
measurement of product formation
0.805
(+)-5-chloromuconolactone
-
-
0.0182
2,4-dichloro-cis,cis-muconate
-
-
0.119
2,4-dichloro-cis,cis-muconate
-
-
0.0559
2-chloro-cis,cis-muconate
Q8G9L1
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
Q8G9L1
pH and temperature not specified in the publication
0.052
3-Fluoro-cis,cis-muconate
-
-
0.0134
3-methyl-cis,cis-muconate
-
-
0.0487
3-methyl-cis,cis-muconate
Q8G9L1
pH and temperature not specified in the publication
0.066
3-methyl-cis,cis-muconate
-
-
0.0813
cis,cis-Muconate
Q8G9L1
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
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2.12
(+)-2-Chloromuconolactone
-
measurement of substrate consumption
3.95
(+)-2-Chloromuconolactone
-
measurement of product formation
24.7
(+)-5-chloromuconolactone
-
-
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
Q8G9L1
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
-
-
0.0567
2-Methyl-cis,cis-muconate
-
-
8.8
3-chloro-cis,cis-muconate
Q8G9L1
pH and temperature not specified in the publication
57.7
3-chloro-cis,cis-muconate
-
-
60.7
3-chloro-cis,cis-muconate
-
-
6.07
3-Fluoro-cis,cis-muconate
-
-
0.8
3-methyl-cis,cis-muconate
-
-
3.2
3-methyl-cis,cis-muconate
Q8G9L1
pH and temperature not specified in the publication
4.33
cis,cis-Muconate
-
-
24.66
cis,cis-Muconate
Q8G9L1
pH and temperature not specified in the publication
additional information
additional information
-
-
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
65
2-chloro-cis,cis-muconate
Q8G9L1
pH and temperature not specified in the publication
2005
6.66
3-chloro-cis,cis-muconate
Q8G9L1
pH and temperature not specified in the publication
1912
65
3-methyl-cis,cis-muconate
Q8G9L1
pH and temperature not specified in the publication
2009
303
cis,cis-Muconate
Q8G9L1
pH and temperature not specified in the publication
1375
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.7
-
in borate-phosphate-acetate buffer
6.2
-
in bis-Tris-HCl and Tris-HCl buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 8.5
-
pH 6: about 60% of maximal activity, pH 8.5: about 40% of maximal activity
7.2 - 8.2
-
4 C, 36 h, 40 mM Tris-HCl, MOPS or HEPES buffer, enzyme concentration 0.03 mg/ml
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PDB
SCOP
CATH
ORGANISM
Cupriavidus pinatubonensis (strain JMP 134 / LMG 1197)
Pseudomonas sp. (strain P51)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
230000 - 250000
-
gel filtration, nondenaturing electrophoresis
3656
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 40000-42000, SDS-PAGE
?
-
x * 39000, SDS-PAGE
?
-
x * 38000-40000, SDS-PAGE
?
-
x * 39780, calculation from nucleotide sequence
?
Rhodococcus erythropolis 1CP
-
x * 40000-42000, SDS-PAGE
-
homooctamer
Q8G9L1
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure at 3 A resolution
-
re-evaluation of the crystal structure
-
the crystallographic structure of the homooctameric Rho-2-CMCI is solved at 2.5 A resolution by molecular replacement using the coordinates of the structure of chloromuconate cycloisomerase from Pseudomonas putida PRS2000
Q8G9L1
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
60
-
10 min, strongly effected
3647
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, 24 h, complete loss of activity
-
4°C, enzyme concentration 0.45 mg/ml, 50 mM Tris-HCl buffer, pH 7.5, 2 mM MnSO4, 0.2 M NaCl, 50% loss of activity after 3.5 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
anion-exchange chromatography on DEAE-Toyopearl, hydrophobic chromatography on Phenyl-sepharose with linear gradient (NH4)2SO4, anion-exchange Q3 chromatography and hydrophobic chromatography
Q8G9L1
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE