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
5.3.3.4
-
RECOMMENDED NAME
GeneOntology No.
muconolactone DELTA-isomerase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
(S)-5-oxo-2,5-dihydrofuran-2-acetate = 5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
-
-
-
-
(S)-5-oxo-2,5-dihydrofuran-2-acetate = 5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
stereochemical course
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
intramolecular oxidoreduction
-
-
-
-
isomerization
-
-
-
-
isomerization
C5MR75, -
-
isomerization
Pseudomonas reinekei MT1
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
4-methylcatechol degradation (ortho cleavage)
-
Benzoate degradation
-
catechol degradation to beta-ketoadipate
-
Metabolic pathways
-
Microbial metabolism in diverse environments
-
SYSTEMATIC NAME
IUBMB Comments
5-oxo-4,5-dihydrofuran-2-acetate Delta3-Delta2-isomerase
-
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
CATC
-
gene name
Isomerase, muconolactoneDELTA-
-
-
-
-
Methylmuconolactone isomerase
-
-
-
-
Methylmuconolactone isomerase
C5MR75
-
Methylmuconolactone isomerase
Pseudomonas reinekei MT1
C5MR75
-
-
MI
-
-
-
-
MIase
-
-
-
-
MmlJ
Pseudomonas reinekei MT1
C5MR75
-
-
Muconolactone DELTA-isomerase
-
-
-
-
Muconolactone isomerase
-
-
-
-
Muconolactone isomerase
C5MR75
-
Muconolactone isomerase
Pseudomonas reinekei MT1
C5MR75
-
-
CAS REGISTRY NUMBER
COMMENTARY
37318-46-0
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
basonym Alcaligenes eutrophus; strain JMP134
-
-
Manually annotated by BRENDA team
strain PRS2113
-
-
Manually annotated by BRENDA team
Pseudomonas putida PRS2113
strain PRS2113
-
-
Manually annotated by BRENDA team
strain MT1
UniProt
Manually annotated by BRENDA team
Pseudomonas reinekei MT1
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 ACCESSION NO.
COMMENTARY
LITERATURE
metabolism
C5MR75, -
the mml gene cluster consists of 10 genes encoding enzymes involved in the metabolism of 4-methylmuconolactone
metabolism
Pseudomonas reinekei MT1
-
the mml gene cluster consists of 10 genes encoding enzymes involved in the metabolism of 4-methylmuconolactone
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
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-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-chloro-3-methylmuconolactone
(2S)-chloro(3-methyl-5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
preferred substrate over the natural substrate (4S)-muconolactone
-
-
(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
C5MR75, -
-
-
-
?
(S)-5-oxo-2,5-dihydrofuran-2-acetate
5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
Pseudomonas reinekei MT1
C5MR75
-
-
-
?
3-methylmuconolactone
4-methyl-3-oxoadipate enol-lactone
show the reaction diagram
C5MR75, -
-
-
-
?
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
?
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
(4S)-(+)-muconolactone
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
(4S)-(+)-muconolactone
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
Pseudomonas putida A.3.12.
-
-
-
-
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
-
-
-
-
?
muconolactone
(5-oxo-4,5-dihydrofuran-2-yl)acetic acid
show the reaction diagram
Pseudomonas putida PRS2113
-
-
-
-
muconolactone
3-oxoadipate enol-lactone
show the reaction diagram
C5MR75, -
-
-
-
?
muconolactone
3-oxoadipate enol-lactone
show the reaction diagram
Pseudomonas reinekei MT1
C5MR75
-
-
-
?
3-methylmuconolactone
4-methyl-3-oxoadipate enol-lactone
show the reaction diagram
Pseudomonas reinekei MT1
C5MR75
-
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
constitutive enzyme
-
-
-
additional information
?
-
-
enzyme is required for the dissimilation of benzoate to beta-ketoadipate
-
-
-
additional information
?
-
-
enzyme of beta-ketoadipate pathway
-
-
-
additional information
?
-
-
enzyme of beta-ketoadipate pathway
-
-
-
additional information
?
-
-
formation of protoanemonin from 2-chloro-cis,cis-muconate by the combined action of muconate cycloisomerase and muconolactone isomerase
-
?
additional information
?
-
Pseudomonas putida A.3.12.
-
enzyme of beta-ketoadipate pathway
-
-
-
additional information
?
-
-
constitutive enzyme
-
-
-
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
(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
C5MR75, -
-
-
-
?
(S)-5-oxo-2,5-dihydrofuran-2-acetate
5-oxo-4,5-dihydrofuran-2-acetate
show the reaction diagram
Pseudomonas reinekei MT1
C5MR75
-
-
-
?
3-methylmuconolactone
4-methyl-3-oxoadipate enol-lactone
show the reaction diagram
C5MR75, -
-
-
-
?
muconolactone
3-oxoadipate enol-lactone
show the reaction diagram
C5MR75, -
-
-
-
?
muconolactone
3-oxoadipate enol-lactone
show the reaction diagram
Pseudomonas reinekei MT1
C5MR75
-
-
-
?
3-methylmuconolactone
4-methyl-3-oxoadipate enol-lactone
show the reaction diagram
Pseudomonas reinekei MT1
C5MR75
-
-
-
?
additional information
?
-
-
-
-
-
-
additional information
?
-
-
constitutive enzyme
-
-
-
additional information
?
-
-
enzyme is required for the dissimilation of benzoate to beta-ketoadipate
-
-
-
additional information
?
-
-
enzyme of beta-ketoadipate pathway
-
-
-
additional information
?
-
-
enzyme of beta-ketoadipate pathway
-
-
-
additional information
?
-
-
formation of protoanemonin from 2-chloro-cis,cis-muconate by the combined action of muconate cycloisomerase and muconolactone isomerase
-
?
additional information
?
-
Pseudomonas putida A.3.12.
-
enzyme of beta-ketoadipate pathway
-
-
-
additional information
?
-
-
constitutive enzyme
-
-
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
(4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
isomerization of (4R,5R)-(+/-)-5-chloro-3-methylmuconolactone
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.66
-
(4R,5R)-5-chloro-3-methylmuconolactone
-
pH 7.5, 25C
0.66
-
(4R,5R/4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
-
9.8
-
(4R,5R/4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
-
5.2
-
(4R,5S)-(+)-5-Chloromuconolactone
-
-
10.3
-
(4R,5S)-(+)-5-Chloromuconolactone
-
-
10.3
-
(4R,5S)-5-chloromuconolactone
-
pH 7.5, 25C
6
-
(4S)-(+)-muconolactone
-
-
8.9
-
(4S)-(+)-muconolactone
-
-
3.6
-
(4S)-2-chloromuconolactone
-
pH 7.5, 25C
6
-
(4S)-muconolactone
-
pH 7.5, 25C
0.08
-
muconolactone
-
-
0.64
-
muconolactone
-
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
42.5
-
(4R,5R)-5-chloro-3-methylmuconolactone
-
pH 7.5, 25C
42.5
-
(4R,5R/4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
-
267
-
(4R,5R/4S,5S)-(+/-)-5-chloro-3-methylmuconolactone
-
-
317
-
(4R,5S)-(+)-5-Chloromuconolactone
-
-
5950
-
(4R,5S)-(+)-5-Chloromuconolactone
-
-
5950
-
(4R,5S)-5-chloromuconolactone
-
pH 7.5, 25C
367
-
(4S)-(+)-muconolactone
-
-
683
-
(4S)-(+)-muconolactone
-
-
0.03
0.55
(4S)-2-chloromuconolactone
-
pH 7.5, 25C
7.17
-
(4S)-2-chloromuconolactone
-
pH 7.5, 25C
286
-
(4S)-muconolactone
-
pH 7.5, 25C
66.67
-
muconolactone
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
-
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.5
8.5
-
-
9
-
-
5R/4R,5S)-(+/-)-5-chloro-3-methylmuconolactone, more active in potassium sodium phosphate buffer than in Tris/HCl or borate buffer
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
9.5
-
pH 7: about 80% of maximal activity, pH 9.5: about 70% of maximal activity
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
10000
-
C5MR75, -
determined by SDS-PAGE
89000
-
-
gel filtration
93000
-
-
gel filtration
93000
-
-
-
94000
-
-
gel filtration
100000
-
-
gel filtration
100000
-
-
gel filtration
111000
-
-
sedimentation equilibrium ultracentrifugation
additional information
-
-
partial amino acid sequence of cyanogen bromide fragments of the enzyme
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
-
x * 12000, SDS-PAGE
?
-
x * 12000, SDS-PAGE
?
-
x * 11500, SDS-PAGE
?
-
x * 10300, SDS-PAGE
decamer
-
or dodecamer, 10 * or 12 * 11300, SDS-PAGE. Oligomer may be composed of two stacked discs of pentamers or hexamers
decamer
-
10 * 11000, crystallographic data, decamer with a 5fold symmetry axis
decamer
-
10 * 10100, SDS-PAGE
dodecamer
-
or decamer, 12 * or 10 * 11300, SDS-PAGE. Oligomer may be composed of two stacked discs of pentamers or hexamers
octamer
-
8 * 12000, SDS-PAGE
octamer
-
8 * 12000, SDS-PAGE
-
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
crystal structure at 3.3 A resolution
-
low resolution crystal structure
-
pH STABILITY
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
10.5
-
stable
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
55
-
-
half-life: 2.5 h
65
-
-
rapid inactivation at
70
-
-
20 min, stable up to
90
-
-
20 min, 25% loss of activity
90
-
-
pH 8.0, 10 min, enzyme maintains more than 80% of activity
95
-
-
pH 8.0, 10 min, enzyme maintains 64% of activity
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
resistant to proteolytic cleavage by trypsin
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
4C, pH 7.5, 100 mM potassium sodium phosphate, 3 months stable
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
ammonium sulfate precipitation
-
MmlJ is partially purified by anion exchange chromatography using a MonoQ HR 5/5 column
C5MR75, -
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression in Pseudomonas putida and Escherichia coli
-
expressed in Escherichia coli strain H7
-
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
-
a 75-bp and a 125-bp fragment of the mmlJ gene are cloned into the vector pGEM-T Easy
C5MR75, -
EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
the cat genes are induced by phenol and benzoate
-