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EC Tree
The enzyme appears in viruses and cellular organisms
Synonyms
4-Methyl-3-enelactone methyl isomerase, 4-Methylmuconolactone methylisomerase, Isomerase, 4-methyl-2-enelactone, methymuconolactone isomerase, MLMI, MmlJ,
more
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4-Methyl-3-enelactone methyl isomerase
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4-Methylmuconolactone methylisomerase
Isomerase, 4-methyl-2-enelactone
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methymuconolactone isomerase
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4-Methylmuconolactone methylisomerase
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4-Methylmuconolactone methylisomerase
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4-Methylmuconolactone methylisomerase
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4-Methylmuconolactone methylisomerase
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4-Methylmuconolactone methylisomerase
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MLMI
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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
mechanism
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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
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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intramolecular transfer reaction
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4-Carboxymethyl-4-methylbut-2-en-1,4-olide methylmutase
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(4R,5R)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
(4S)-4-methylmuconolactone
(4S)-3-methylmuconolactone
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?
(4S,5S)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
1-methylbis-lactone
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?
1-Methylbislactone
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
3-methylmuconolactone
4-methyl-3-oxoadipate enollactone
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?
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
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enzyme of the modified 3-oxoadipate pathway in the Gram-negative bacterium Alcaligenes eutrophus JMP 134
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4-methyl-muconolactone
3-methyl-muconolactone
additional information
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(4R,5R)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
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r
(4R,5R)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
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r
(4S,5S)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
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r
(4S,5S)-5-chloro-3-methylmuconolactone
trans-3-methyldienelactone
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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
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1-Methylbislactone
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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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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4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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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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4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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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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4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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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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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
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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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4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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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
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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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4-Carboxymethyl-4-methylbut-2-en-1,4-olide
4-Carboxymethyl-3-methylbut-2-en-1,4-olide
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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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4-methyl-muconolactone
3-methyl-muconolactone
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r
4-methyl-muconolactone
3-methyl-muconolactone
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r
additional information
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not: isomeric methyl-substituted 4-carboxymethylbut-2-en-4-olides
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additional information
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activity with 3-methyl-cis,cis-muconate is below the detection limit
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additional information
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activity with 3-methyl-cis,cis-muconate is below the detection limit
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4-Carboxymethyl-4-methylbut-2-en-1,4-olide
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enzyme of the modified 3-oxoadipate pathway in the Gram-negative bacterium Alcaligenes eutrophus JMP 134
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4-methyl-muconolactone
3-methyl-muconolactone
4-methyl-muconolactone
3-methyl-muconolactone
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r
4-methyl-muconolactone
3-methyl-muconolactone
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r
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(-)1-Methyl-8-bromobislactone
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weak
2,4-dimethyl-2-enelactone
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weak
2-Bromo-4-methylbutan-1,4-olide
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weak
2-Bromobutan-1,4-olide
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2-Methyl-2-enelactone
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weak
2-Methylbutan-1,4-olide
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3-methyl-2-enelactone
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weak
4-carboxymethylbut-2-en-4-olide
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4-methyl-2-enelactone
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weak
4-Methylbut-3-en-1,4-olide
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angelicalactone
4-methylbutan-1,4-olide
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trans-dienelactone
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weak
4-chloromercuribenzoate
inhibition is reversible by DTT
4-chloromercuribenzoate
remaining activity of 6% after incubation with 0.02 mM 4-chloromercuribenzoate for 30 min
CuSO4
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PCMB
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additional information
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not: isomeric methyl-substituted 4-carboxymethylbut-2-en-4-olides
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additional information
no inhibition by EDTA
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additional information
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no inhibition by EDTA
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additional information
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EDTA
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0.045 - 0.4583
(4S)-4-methylmuconolactone
0.028
1-methyl-3,7-dioxo-2,6-dioxabicyclo[3.3.0]octane
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0.17
1-methyl-bislactone
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0.176 - 0.23
4-carboxymethyl-4-methylbut-2-en-1,4-olide
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
0.176
4-carboxymethyl-4-methylbut-2-en-1,4-olide
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0.23
4-carboxymethyl-4-methylbut-2-en-1,4-olide
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5.8 - 47.2
(4S)-4-methylmuconolactone
3.75
1-methyl-3,7-dioxo-2,6-dioxabicyclo[3.3.0]octane
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98.5
4-carboxymethyl-4-methylbut-2-en-1,4-olide
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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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100 - 500
(4S)-4-methylmuconolactone
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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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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6 - 8.5
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active in this range, rapid decrease of activity above pH 8.5
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25
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assay at
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gene mmlI
UniProt
brenda
N657
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brenda
N657
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brenda
N5
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brenda
N75
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brenda
N75
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brenda
N75
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brenda
strains BCN1, BCN2 and 4PH1
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brenda
basonym Alcaligenes eutrophus
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brenda
gene mmlI
UniProt
brenda
JMP 134, cloned into Pseudomonas sp. B13 FR1
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brenda
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brenda
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UniProt
brenda
N5
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brenda
N75
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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brenda
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physiological function
the enzyme is involved in the modified ortho-cleavage pathway and methylmuconolactone degradation of Ralstonia eutropha strain JMP134
physiological function
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the enzyme is involved in the modified ortho-cleavage pathway and methylmuconolactone degradation of Ralstonia eutropha strain JMP134
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C5MR76_9PSED
107
0
12540
TrEMBL
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O51799_CUPNE
113
0
12874
TrEMBL
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12900
2 * 12900, about, sequence calculation
17000
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4 * 17000, Rhodococcus rhodochrous, SDS-PAGE
40000
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1 * 40000, Alcaligenes eutrophus (JMP 134, cloned into Pseudomonas sp. B13 FR1), SDS-PAGE
75500
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Rhodococcus rhodochrous, gel filtration
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monomer
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1 * 40000, Alcaligenes eutrophus (JMP 134, cloned into Pseudomonas sp. B13 FR1), SDS-PAGE
homodimer
2 * 12900, about, sequence calculation
homodimer
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2 * 12900, about, sequence calculation
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homodimer
x-ray crystallography
tetramer
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4 * 17000, Rhodococcus rhodochrous, SDS-PAGE
tetramer
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4 * 17000, Rhodococcus rhodochrous, SDS-PAGE
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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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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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Chelating agents like EDTA or thiol-group modifying reagents like DTT stabilize
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-30°C, slow loss of activity on prolonged storage
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4°C or -20°C, highly purified enzyme is rather unstable
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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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JMP 134, cloned into Pseudomonas sp. B13 FR1
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MonoQ column chromatography
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Strep-Tactin-Sepharose column chromatography
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expressed in Escherichia coli JM109 cells
gene mmlI, DNA and amino acid sequence determination and analysis, expression in Escherichia coli strain BL21(DE3)
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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
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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)
brenda
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