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 hide
5.5.1.7
-
RECOMMENDED NAME
GeneOntology No.
Chloromuconate cycloisomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(2R)-2-chloro-2,5-dihydro-5-oxofuran-2-acetate = 3-chloro-cis,cis-muconate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
elimination/addition
-
-
intramolecular
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
2,4-dichlorotoluene degradation
-
-
2,5-dichlorotoluene degradation
-
-
3,4-dichlorotoluene degradation
-
-
3-chlorocatechol degradation
-
-
3-chlorocatechol degradation I (ortho)
-
-
3-chlorocatechol degradation II (ortho)
-
-
4,5-dichlorocatechol degradation
-
-
4-chlorocatechol degradation
-
-
4-methylcatechol degradation (ortho cleavage)
-
-
5-chloro-3-methyl-catechol degradation
-
-
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 on 2-chloro-cis,cis-muconate. Not identical with EC 5.5.1.1 (muconate cycloisomerase) or EC 5.5.1.11 (dichloromuconate cycloisomerase).
CAS REGISTRY NUMBER
COMMENTARY hide
95990-33-3
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain A7-2
-
-
Manually annotated by BRENDA team
strain A7-2
-
-
Manually annotated by BRENDA team
Cupriavidus necator JMP134(pJP4)
JMP134(pJP4)
-
-
Manually annotated by BRENDA team
strain RD330 a transposon mutant of JMP134
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
DH1(pDC100), pAC27-encoded enzyme
-
-
Manually annotated by BRENDA team
B13
-
-
Manually annotated by BRENDA team
strain PS12
-
-
Manually annotated by BRENDA team
strain PS12
-
-
Manually annotated by BRENDA team
1CP
-
-
Manually annotated by BRENDA team
strain1CP
-
-
Manually annotated by BRENDA team
14p1
-
-
Manually annotated by BRENDA team
14p1
-
-
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-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
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
2-chloro-4-methylmuconate
5-chloro-3-methylmuconolactone + 2-chloro-4-methylmuconolactone
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
5-Chloromuconolactone
show the reaction diagram
2-Methyl-cis,cis-muconate
?
show the reaction diagram
3-Bromo-cis,cis-muconate
Corresponding (E)-dienelactone
show the reaction diagram
3-chloro-2-methylmuconate
5-methyl-cis-dienelactone + 2-chloro-3-methylmuconolactone
show the reaction diagram
3-chloro-2-methylmuconolactone + 3-chloro-2-methylmuconolactone
?
show the reaction diagram
3-Chloro-cis,cis-muconate
cis-4-Carboxymethylenebut-2-en-4-olide
show the reaction diagram
3-Fluoro-cis,cis-muconate
?
show the reaction diagram
-
-
-
-
-
3-Methyl-cis,cis-muconate
?
show the reaction diagram
4-chloro-2-methylmuconate
2-methyl-cis-dienelactone + 3-chloro-5-methylmuconolactone
show the reaction diagram
cis,cis-Muconate
?
show the reaction diagram
additional information
?
-
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
additional information
?
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2.12 - 3.95
(+)-2-Chloromuconolactone
24.7
(+)-5-chloromuconolactone
Cupriavidus necator
-
-
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
Rhodococcus erythropolis
-
-
8.8 - 60.7
3-chloro-cis,cis-muconate
6.07
3-fluoro-cis,cis-muconate
Rhodococcus erythropolis
-
-
0.8 - 3.2
3-methyl-cis,cis-muconate
4.33 - 24.66
cis,cis-muconate
additional information
additional information
Pseudomonas sp.
-
-
-
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
65
2-chloro-cis,cis-muconate
Rhodococcus opacus
Q8G9L1
pH and temperature not specified in the publication
2005
6.66
3-chloro-cis,cis-muconate
Rhodococcus opacus
Q8G9L1
pH and temperature not specified in the publication
1912
65
3-methyl-cis,cis-muconate
Rhodococcus opacus
Q8G9L1
pH and temperature not specified in the publication
2009
303
cis,cis-muconate
Rhodococcus opacus
Q8G9L1
pH and temperature not specified in the publication
1375
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.7
-
in borate-phosphate-acetate buffer
6.2
-
in bis-Tris-HCl and Tris-HCl buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
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 hide
LITERATURE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Cupriavidus pinatubonensis (strain JMP 134 / LMG 1197)
Pseudomonas sp. (strain P51)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
230000 - 250000
-
gel filtration, nondenaturing electrophoresis
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60
-
10 min, strongly effected
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
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE