Information on EC 5.5.1.11 - dichloromuconate cycloisomerase

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The expected taxonomic range for this enzyme is: Cupriavidus

EC NUMBER
COMMENTARY hide
5.5.1.11
-
RECOMMENDED NAME
GeneOntology No.
dichloromuconate cycloisomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2,4-dichloro-2,5-dihydro-5-oxofuran-2-acetate = 2,4-dichloro-cis,cis-muconate
show the reaction diagram
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-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
intramolecular lyase reaction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
1,4-dichlorobenzene degradation
-
-
3,5-dichlorocatechol degradation
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-
Chlorocyclohexane and chlorobenzene degradation
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Microbial metabolism in diverse environments
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-
SYSTEMATIC NAME
IUBMB Comments
2,4-dichloro-2,5-dihydro-5-oxofuran-2-acetate lyase (decyclizing)
Requires Mn2+. The product of cycloisomerization of dichloro-cis,cis-muconate spontaneously eliminates chloride to produce cis-4-carboxymethylene-3-chlorobut-2-en-4-olide. Also acts, in the reverse direction, on cis,cis-muconate and its monochloro-derivatives, but with lower affinity. Not identical with EC 5.5.1.1 (muconate cycloisomerase) or EC 5.5.1.7 (chloromuconate cycloisomerase).
CAS REGISTRY NUMBER
COMMENTARY hide
126904-95-8
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
JMP 134
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-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,4-dichloro-cis,cis-muconate
4-carboxymethylene-3-chlorobut-2-en-4-olide + HCl
show the reaction diagram
2-chloro-4-methyl-cis,cis-muconate
2-chloro-4-methyl-muconolactone
show the reaction diagram
-
-
4-carboxymethyl-2-chlorobut-4-methylbut-2-en-4-olide
?
2-Chloro-cis,cis-muconate
?
show the reaction diagram
2-Methyl-cis,cis-muconate
?
show the reaction diagram
3-chloro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
?
3-Methyl-cis,cis-muconate
?
show the reaction diagram
cis,cis-Muconate
?
show the reaction diagram
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2,4-dichloro-cis,cis-muconate
4-carboxymethylene-3-chlorobut-2-en-4-olide + HCl
show the reaction diagram
-
enzyme is involved in 3,5-dichloro-catechol metabolism
The intermediate (2,4-dichloro-5-oxo-2,5-dihydrofuran-2-yl)acetic acid (i.e. 3,5-dichloro-2,5-dihydro-2-oxofuran-5-acetate) is spontanously dehalogenated to 4-carboxymethylene-3-chlorobut-2-en-4-olide (i.e. 2-chlorodienelactone)
ir
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
-
thiol groups required
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Mn2+
-
requirement
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
EDTA
-
1.3 mM
phosphate
-
-
succinate
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.02
2,4-dichloro-cis,cis-muconate
-
-
0.06
2-chloro-4-methyl-cis,cis-muconate
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pH 8.0
0.502
2-chloro-cis,cis-muconate
-
-
0.128
2-methyl-cis,cis-muconate
-
-
0.304
3-chloro-cis,cis-muconate
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-
0.158
3-methyl-cis,cis-muconate
-
-
4.2
cis,cis-muconate
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-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
63.7
2,4-dichloro-cis,cis-muconate
Cupriavidus necator
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-
15.8
2-chloro-cis,cis-muconate
Cupriavidus necator
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-
10.2
2-methyl-cis,cis-muconate
Cupriavidus necator
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-
119
3-chloro-cis,cis-muconate
Cupriavidus necator
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-
54.8
3-methyl-cis,cis-muconate
Cupriavidus necator
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-
51.5
cis,cis-muconate
Cupriavidus necator
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-
additional information
additional information
Cupriavidus necator
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kcat of 2-chloro-4-methyl-cis,cis-musconate is about 55% of that found for 2,4-dichloro-cis,cis-musconate
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.13
-
enzyme from cells induced with 2-chloro-4-methylphenoxyacetic acid
0.24
-
enzyme from cells induced with 2,4-dichlorophenoxyacetic acid
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 8
-
above 80% of activity maximum at pH 5.5 and 8
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
40000
-
6 * 40000, SDS-PAGE
270000
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gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexamer
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-16°C, without MnSO4, 95% loss of activity after 10 days
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4°C, pH 7.5-8.5, 10-30% loss of activity after 24 h
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE