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Information on EC 5.4.99.14 - 4-carboxymethyl-4-methylbutenolide mutase
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5.4.99.14 4-carboxymethyl-4-methylbutenolide mutaseSpecify your search results
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
4-Methyl-3-enelactone methyl isomerase, 4-Methylmuconolactone methylisomerase, Isomerase, 4-methyl-2-enelactone, methymuconolactone isomerase, MLMI, MmlJ, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
4-Methyl-3-enelactone methyl isomerase
-
-
-
-
4-Methylmuconolactone methylisomerase
Isomerase, 4-methyl-2-enelactone
-
-
-
-
MLMI
4-Methylmuconolactone methylisomerase
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
4-Carboxymethyl-4-methylbut-2-en-1,4-olide = 4-carboxymethyl-3-methylbut-2-en-1,4-olide
mechanism
-
4-Carboxymethyl-4-methylbut-2-en-1,4-olide = 4-carboxymethyl-3-methylbut-2-en-1,4-olide
isomerization does not involve actual methyl migration, but proceeds via the 1-methylbislactone
-
4-Carboxymethyl-4-methylbut-2-en-1,4-olide = 4-carboxymethyl-3-methylbut-2-en-1,4-olide
isomerization does not involve actual methyl migration, but proceeds via the 1-methylbislactone
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-
4-Carboxymethyl-4-methylbut-2-en-1,4-olide = 4-carboxymethyl-3-methylbut-2-en-1,4-olide
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-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
intramolecular transfer reaction
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-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
4-Carboxymethyl-4-methylbut-2-en-1,4-olide methylmutase
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CAS REGISTRY NUMBER
COMMENTARY
115300-03-3
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
?
-
enzyme of the modified 3-oxoadipate pathway in the Gram-negative bacterium Alcaligenes eutrophus JMP 134
-
-
?
(4R,5R)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
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-
-
r
(4R,5R)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
-
-
-
r
(4S,5S)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
-
-
-
r
(4S,5S)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
-
-
-
r
1-Methylbislactone
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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i.e. 1-methyl-3,7-dioxo-2,6-dioxabicyclo[3.3.0]octane
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-
?
1-Methylbislactone
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
1-Methylbislactone
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
highly specific, accepts only (+)-(4S)-4-methylmuconolactone, i.e. 4-carboxymethyl-4-methylbut-2-en-1,4-olide and the putative reaction intermediate 1-methylbislactone
i.e. (-)-(4S)-3-methylmuconolactone
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
highly specific, accepts only (+)-(4S)-4-methylmuconolactone, i.e. 4-carboxymethyl-4-methylbut-2-en-1,4-olide and the putative reaction intermediate 1-methylbislactone
i.e. (-)-(4S)-3-methylmuconolactone
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
-
-
-
?
additional information
?
-
-
not: isomeric methyl-substituted 4-carboxymethylbut-2-en-4-olides
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-
?
additional information
?
-
activity with 3-methyl-cis,cis-muconate is below the detection limit
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-
?
additional information
?
-
-
activity with 3-methyl-cis,cis-muconate is below the detection limit
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-Carboxymethyl-4-methylbut-2-en-1,4-olide
?
-
enzyme of the modified 3-oxoadipate pathway in the Gram-negative bacterium Alcaligenes eutrophus JMP 134
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
4-chloromercuribenzoate
remaining activity of 6% after incubation with 0.02 mM 4-chloromercuribenzoate for 30 min
additional information
-
not: isomeric methyl-substituted 4-carboxymethylbut-2-en-4-olides
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.045
(4S)-4-methylmuconolactone
mutant enzyme Y39F, in phosphate buffer, 50 mM, pH 7.3
0.052
(4S)-4-methylmuconolactone
wild type enzyme, in phosphate buffer, 50 mM, pH 7.3
0.0972
(4S)-4-methylmuconolactone
mutant enzyme C67S, in phosphate buffer, 50 mM, pH 7.3
0.4583
(4S)-4-methylmuconolactone
mutant enzyme H52A, in phosphate buffer, 50 mM, pH 7.3
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
5.8
(4S)-4-methylmuconolactone
mutant enzyme Y39F, in phosphate buffer, 50 mM, pH 7.3
7.3
(4S)-4-methylmuconolactone
mutant enzyme C67S, in phosphate buffer, 50 mM, pH 7.3
24.2
(4S)-4-methylmuconolactone
wild type enzyme, in phosphate buffer, 50 mM, pH 7.3
47.2
(4S)-4-methylmuconolactone
mutant enzyme H52A, in phosphate buffer, 50 mM, pH 7.3
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
100
(4S)-4-methylmuconolactone
mutant enzyme C67S, in phosphate buffer, 50 mM, pH 7.3
100
(4S)-4-methylmuconolactone
mutant enzyme H52A, in phosphate buffer, 50 mM, pH 7.3
100
(4S)-4-methylmuconolactone
mutant enzyme Y39F, in phosphate buffer, 50 mM, pH 7.3
500
(4S)-4-methylmuconolactone
wild type enzyme, in phosphate buffer, 50 mM, pH 7.3
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
28.8
toward 1-methylbis-lactone, in phosphate buffer, 50 mM, pH 7.3
57.3
toward (4S)-4-methylmuconolactone, in phosphate buffer, 50 mM, pH 7.3
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6 - 8.5
-
active in this range, rapid decrease of activity above pH 8.5
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
25
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
the enzyme is involved in the modified ortho-cleavage pathway and methylmuconolactone degradation of Ralstonia eutropha strain JMP134
physiological function
-
the enzyme is involved in the modified ortho-cleavage pathway and methylmuconolactone degradation of Ralstonia eutropha strain JMP134
-
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
40000
-
1 * 40000, Alcaligenes eutrophus (JMP 134, cloned into Pseudomonas sp. B13 FR1), SDS-PAGE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
homodimer
monomer
-
1 * 40000, Alcaligenes eutrophus (JMP 134, cloned into Pseudomonas sp. B13 FR1), SDS-PAGE
tetramer
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
in complex with (4S)-4-methylmuconolactone and (4S)-3-methylmuconolactone, sitting drop vapor diffusion method, at 19°C, using 25% (w/v) polyethylene glycol 1500, 0.1 M MMT buffer, pH 5 (DL-malic acid, MES, and Tris base in a 1:2:2 molar ratio)
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C67S
incubation of variant C67S with 4-chloromercuribenzoate does not significantly decrease its activity (above 65% of activity remaining after a 30-min incubation)
H26A
the mutant shows a marked decrease in catalytic activity (kcat) by two orders of magnitude
H52A
the mutation results in an increase in Km by a factor of 9, but only a small change in kcat
Y39F
the mutant displays reduced activity compared to the wild type enzyme
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
Chelating agents like EDTA or thiol-group modifying reagents like DTT stabilize
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
4°C, 24 h, 10% loss of activity, highly purified enzyme, 5% loss of activity with addition of chelating agents like EDTA or thiol-group modifying reagents like DTT
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
gene mmlI, DNA and amino acid sequence determination and analysis, expression in Escherichia coli strain BL21(DE3)
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Bruce, N.C.; Cain, R.B.
beta-Methylmuconolactone, a key intermediate in the dissimilation of methylaromatic compounds by a modified 3-oxoadipate pathway evolved in nocardioform actinomycetes
FEMS Microbiol. Lett.
50
233-239
1988
Gordonia rubripertincta, Rhodococcus ruber, Rhodococcus rhodochrous, Rhodococcus sp., Rhodococcus rhodochrous N5, Gordonia rubripertincta N657, Rhodococcus ruber N75
-
brenda
Bruce, N.C.; Cain, R.B.; Pieper, D.H.; Engesser, K.H.
Purification and characterization of 4-methylmuconolactone methyl-isomerase, a novel enzyme of the modified 3-oxoadipate pathway in nocardioform actinomycetes
Biochem. J.
262
303-312
1989
Rhodococcus rhodochrous, Rhodococcus rhodochrous N75
brenda
Pieper, D.H.; Stadler-Fritzsche, K.; Knackmuss, H.J.; Engesser, K.H.; Bruce, N.C.; Cain, R.B.
Purification and characterization of 4-methylmuconolactone methylisomerase, a novel enzyme of the modified 3-oxoadipate pathway in the gram-negative bacterium Alcaligenes eutrophus JMP 134
Biochem. J.
271
529-534
1990
Cupriavidus necator
brenda
Marin, M.; Perez-Pantoja, D.; Donoso, R.; Wray, V.; Gonzalez, B.; Pieper, D.H.
Modified 3-oxoadipate pathway for the biodegradation of methylaromatics in Pseudomonas reinekei MT1
J. Bacteriol.
192
1543-1552
2010
Pseudomonas reinekei
brenda
Marin, M.; Heinz, D.W.; Pieper, D.H.; Klink, B.U.
Crystal structure and catalytic mechanism of 4-methylmuconolactone methylisomerase
J. Biol. Chem.
284
32709-32716
2009
Pseudomonas reinekei (C5MR76), Pseudomonas reinekei
brenda
Erb, R.W.; Timmis, K.N.; Pieper, D.H.
Characterization of a gene cluster from Ralstonia eutropha JMP134 encoding metabolism of 4-methylmuconolactone
Gene
206
53-62
1998
Cupriavidus necator (O51799), Cupriavidus necator, Cupriavidus necator JMP 134-1 (O51799)
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