Information on EC 5.3.3.4 - muconolactone DELTA-isomerase

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The expected taxonomic range for this enzyme is: Bacteria

EC NUMBER
COMMENTARY hide
5.3.3.4
-
RECOMMENDED NAME
GeneOntology No.
muconolactone DELTA-isomerase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(S)-5-oxo-2,5-dihydrofuran-2-acetate = 5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
intramolecular oxidoreduction
-
-
-
-
isomerization
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
4-methylcatechol degradation (ortho cleavage)
-
-
Benzoate degradation
-
-
catechol degradation to beta-ketoadipate
-
-
Metabolic pathways
-
-
Microbial metabolism in diverse environments
-
-
phenol degradation
-
-
SYSTEMATIC NAME
IUBMB Comments
5-oxo-4,5-dihydrofuran-2-acetate Delta3-Delta2-isomerase
-
CAS REGISTRY NUMBER
COMMENTARY hide
37318-46-0
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain PRS2113
-
-
Manually annotated by BRENDA team
strain MT1
UniProt
Manually annotated by BRENDA team
strain MT1
UniProt
Manually annotated by BRENDA team
strain AN-22
-
-
Manually annotated by BRENDA team
strain AN-22
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(4R,5R)-(+/-)-5-chloro-3-methylmuconolactone
2-chloro(3-methyl-5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
(4R,5R)-5-chloro-3-methylmuconolactone
?
show the reaction diagram
(4R,5S)-(+)-5-chloromuconolactone
(2S)-chloro(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
(4R,5S)-(+/-)-5-chloro-3-methylmuconolactone
(2S)-chloro(3-methyl-5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
(4R,5S)-5-chloromuconolactone
?
show the reaction diagram
(4S)-2-chloromuconolactone
?
show the reaction diagram
(4S)-muconolactone
5-oxo-3,4-dihydrofuran-2-acetate
show the reaction diagram
(4S)-Muconolactone
?
show the reaction diagram
(S)-5-oxo-2,5-dihydrofuran-2-acetate
5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
3-methylmuconolactone
4-methyl-3-oxoadipate enol-lactone
show the reaction diagram
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
muconolactone
3-oxoadipate enol-lactone
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
(4S)-Muconolactone
?
show the reaction diagram
(S)-5-oxo-2,5-dihydrofuran-2-acetate
5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
3-methylmuconolactone
4-methyl-3-oxoadipate enol-lactone
show the reaction diagram
muconolactone
3-oxoadipate enol-lactone
show the reaction diagram
additional information
?
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
isomerization of (4R,5R)-(+/-)-5-chloro-3-methylmuconolactone
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.66
(4R,5R)-5-chloro-3-methylmuconolactone
9.8
(4R,5R/4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
-
5.2 - 10.3
(4R,5S)-(+)-5-Chloromuconolactone
10.3
(4R,5S)-5-chloromuconolactone
-
pH 7.5, 25C
6 - 8.9
(4S)-(+)-muconolactone
3.6
(4S)-2-chloromuconolactone
-
pH 7.5, 25C
6
(4S)-muconolactone
-
pH 7.5, 25C
0.08 - 0.64
muconolactone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
42.5
(4R,5R)-5-chloro-3-methylmuconolactone
267
(4R,5R/4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
Cupriavidus necator
-
-
317 - 5950
(4R,5S)-(+)-5-Chloromuconolactone
5950
(4R,5S)-5-chloromuconolactone
Cupriavidus necator
-
pH 7.5, 25C
367 - 683
(4S)-(+)-muconolactone
0.03 - 7.17
(4S)-2-chloromuconolactone
286
(4S)-muconolactone
Cupriavidus necator
-
pH 7.5, 25C
66.67
muconolactone
Rhodococcus sp.
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.5 - 8.5
-
-
7.5 - 9
-
-
9
-
5R/4R,5S)-(+/-)-5-chloro-3-methylmuconolactone, more active in potassium sodium phosphate buffer than in Tris/HCl or borate buffer
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 9.5
-
pH 7: about 80% of maximal activity, pH 9.5: about 70% of maximal activity
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10000
determined by SDS-PAGE
89000
-
gel filtration
94000
-
gel filtration
100000
111000
-
sedimentation equilibrium ultracentrifugation
additional information
-
partial amino acid sequence of cyanogen bromide fragments of the enzyme
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
decamer
dodecamer
-
or decamer, 12 * or 10 * 11300, SDS-PAGE. Oligomer may be composed of two stacked discs of pentamers or hexamers
octamer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure at 3.3 A resolution
-
low resolution crystal structure
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7 - 10.5
-
stable
661015
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
55
-
half-life: 2.5 h
65
-
rapid inactivation at
70
-
20 min, stable up to
95
-
pH 8.0, 10 min, enzyme maintains 64% of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
resistant to proteolytic cleavage by trypsin
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4C, pH 7.5, 100 mM potassium sodium phosphate, 3 months stable
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate precipitation
-
MmlJ is partially purified by anion exchange chromatography using a MonoQ HR 5/5 column
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a 75-bp and a 125-bp fragment of the mmlJ gene are cloned into the vector pGEM-T Easy
catB and catC genes that encode EC 5.5.1.1. and EC 5.3.3.4 respectively, share a single inducible promoter which is located upstream of catB
-
expressed in Escherichia coli strain H7
-
expression in Pseudomonas putida and Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the cat genes are induced by phenol and benzoate
-
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