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 ACCESSION NO.
LITERATURE
2-chloro-2,5-dihydro-5-oxofuran-2-acetate = 3-chloro-cis,cis-muconate
show the reaction diagram
-
-
-
-
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
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
elimination/addition
-
-
intramolecular
-
PATHWAY
KEGG Link
MetaCyc Link
2,4-dichlorotoluene 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 ACCESSION NO.
COMMENTARY
LITERATURE
2-chloro-5-oxo-2,5-dihydrofuran-2-acetate lyase (decyclizing)
-
-
-
-
2CMA-cycloisomerase
-
-
-
-
CMC
-
-
-
-
CMCI
Rhodococcus opacus strain1CP
-
-
-
Isomerase, chloromuconate cyclo-
-
-
-
-
MLE II
-
-
-
-
Muconate cycloisomerase II
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
95990-33-3
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
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 ACCESSION NO.
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
-
-
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
-
-
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
-
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
-
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 ACCESSION NO.
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]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
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
-
-
0.0601
-
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
-
-
0.052
-
3-Fluoro-cis,cis-muconate
-
-
0.0134
-
3-methyl-cis,cis-muconate
-
-
0.066
-
3-methyl-cis,cis-muconate
-
-
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]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
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
-
-
3.83
-
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
-
-
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
-
-
4.33
-
cis,cis-Muconate
-
-
additional information
-
additional information
-
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
2.8
-
-
-
additional information
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.7
-
-
in borate-phosphate-acetate buffer
6.2
-
-
in bis-Tris-HCl and Tris-HCl buffer
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
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
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
PDB
SCOP
CATH
ORGANISM
Cupriavidus pinatubonensis (strain JMP 134 / LMG 1197)
Cytophaga hutchinsonii (strain ATCC 33406 / NCIMB 9469)
Cytophaga hutchinsonii (strain ATCC 33406 / NCIMB 9469)
Pseudomonas sp. (strain P51)
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
230000
250000
-
gel filtration, nondenaturing electrophoresis
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 40000-42000, SDS-PAGE
?
-
x * 39780, calculation from nucleotide sequence
?
-
x * 38000-40000, SDS-PAGE
?
-
x * 39000, SDS-PAGE
?
Rhodococcus erythropolis 1CP
-
x * 40000-42000, SDS-PAGE
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
crystal structure at 3 A resolution
-
re-evaluation of the crystal structure
-
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
60
-
-
10 min, strongly effected
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
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 ACCESSION NO.
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE