5.5.1.1: Muconate cycloisomerase
This is an abbreviated version!
For detailed information about Muconate cycloisomerase, go to the full flat file.
Word Map on EC 5.5.1.1
-
5.5.1.1
-
muconolactone
-
beta-ketoadipate
-
cycloisomerization
-
protoanemonin
-
5-chloromuconolactone
-
maleylacetate
-
2-chloro-cis,cis-muconate
-
cutaneum
-
cis-dienelactone
-
chlorocatechols
-
o-succinylbenzoate
-
4-chlorophenol
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5.3.3.4
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3-chloro
-
4-chlorocatechol
-
gerlt
-
phenol-degrading
-
ortho-cleavage
-
trans-dienelactone
- 5.5.1.1
- muconolactone
-
beta-ketoadipate
-
cycloisomerization
- protoanemonin
- 5-chloromuconolactone
- maleylacetate
- 2-chloro-cis,cis-muconate
- cutaneum
- cis-dienelactone
- chlorocatechols
- o-succinylbenzoate
- 4-chlorophenol
-
5.3.3.4
-
3-chloro
- 4-chlorocatechol
-
gerlt
-
phenol-degrading
-
ortho-cleavage
- trans-dienelactone
Reaction
Synonyms
(chloro)-muconate cycloisomerase, (chloro)muconate cycloisomerase, 2-chloromuconate cycloisomerase, ADP1, anti-MLE, CatB, cis,cis-Muconate cycloisomerase, cis,cis-muconate lactonizing enzyme, cis,cis-Muconate-lactonizing enzyme, Enzymes, muconate-lactonizing, Isomerase, muconate cyclo-, MC, MC II, MC O, MCI, MCIase, MCIccaB, MLE, MLE-1, MLE-2, MLEI, muconate cycloisomerase, Muconate cycloisomerase I, Muconate lactonizing enzyme, Rho-2-CMCI, syn-MLE, TcMLE
ECTree
5.5.1.1 Muconate cycloisomeraseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 5.5.1.1 - Muconate cycloisomerase
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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
2,3-dimethyl-cis,cis-muconate
2,3-dimethylmuconolactone
-
-
-
?
2,4-dimethyl-cis,cis-muconate
2,4-dimethylmuconolactone
-
-
-
?
2-chloro-cis,cis-muconate
(+)-2-chloromuconolactone + (+)-5-chloromuconolactone
-
-
mutant enzymes I54V and I54V/Y59W form 5-chloromuconolactone almost exclusively. Mutant enzymes F329I and Y59W form 2-chloromuconolactone as the main product. Mutant enzyme A271S hehaves similar to wild-type enzyme
?
3-Bromo-cis,cis-muconate
?
-
at 9% of the activity relative to 3-methyl-cis,cis-muconate
-
-
?
3-chloro-cis,cis-muconate
protoanemonin + ?
-
-
formed by wild-type enzyme and mutant enzymes I54V, A271S, K276N, F329I, L333V, I54V/F329I
?
3-chloromuconate
cis-dienelactone + protoanemonin
the highest turnover rate, 10fold higher than with 3-methylmuconate, is observed with 3-chloromuconate
-
-
?
cis,cis-muconate
(+)-(4S)-muconolactone
-
syn-cycloisomerization
-
-
?
2-chloro-cis,cis-muconate
5-chloromuconolactone + 2-chloromuconolactone
-
-
?
2-chloro-cis,cis-muconate
5-chloromuconolactone + 2-chloromuconolactone
-
-
-
?
2-chloro-cis,cis-muconate
5-chloromuconolactone + 2-chloromuconolactone
-
-
-
?
2-chloro-cis,cis-muconate
5-chloromuconolactone + 2-chloromuconolactone
-
-
-
-
?
2-chloro-cis,cis-muconate
5-chloromuconolactone + 2-chloromuconolactone
-
-
-
-
?
2-Chloro-cis,cis-muconate
?
-
0.8% of the activity relative to cis,cis-muconate
-
-
?
2-Chloro-cis,cis-muconate
?
-
0.8% of the activity relative to cis,cis-muconate
-
-
?
2-Methyl-cis,cis-muconate
?
-
at 80% of the activity relative to cis,cis-muconate
-
-
?
2-Methyl-cis,cis-muconate
?
-
at 80% of the activity relative to cis,cis-muconate
-
-
?
2-Methyl-cis,cis-muconate
?
-
90% of the activity relative to cis,cis-muconate
-
-
?
2-Methyl-cis,cis-muconate
?
-
90% of the activity relative to cis,cis-muconate
-
-
?
2-Methyl-cis,cis-muconate
?
-
at 6.1% of the activity relative to cis,cis-muconate
-
-
?
2-Methyl-cis,cis-muconate
?
-
at 6.1% of the activity relative to cis,cis-muconate
-
-
?
3-chloro-cis,cis-muconate
4-chloro-muconolactone
-
-
unstable
-
?
3-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
at 11% of the activity relative to 3-methyl-cis,cis-muconate
-
-
?
3-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
7.1% of the activity relative to cis,cis-muconate
-
-
?
3-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
7.1% of the activity relative to cis,cis-muconate
-
-
?
3-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
-
dehalogenation is not catalyzed
?
3-Chloro-cis,cis-muconate
5-Chloromuconolactone
-
-
dehalogenation is not catalyzed
?
3-chloro-cis,cis-muconate
cis-dienelactone + protoanemonin + Cl- + H2O + CO2
-
in vitro activity
product ratio is 76:24, protoanemonin is antibiotically active
-
?
3-chloro-cis,cis-muconate
cis-dienelactone + protoanemonin + Cl- + H2O + CO2
-
in vitro activity
product ratio is 76:24, protoanemonin is antibiotically active
-
?
3-Fluoro-cis,cis-muconate
(+)-4-Fluoromuconolactone
-
at 17% of the activity relative to 3-methyl-cis,cis-muconate
-
-
?
3-Methyl-cis,cis-muconate
?
-
enzyme of the beta-ketoadipate pathway that also functions in the reaction sequence for converting 3-methyl-cis,cis-muconate
-
-
?
3-Methyl-cis,cis-muconate
beta-Methylmuconolactone
-
11.7% of the activity relative to cis,cis-muconate
-
-
?
3-Methyl-cis,cis-muconate
beta-Methylmuconolactone
-
11.7% of the activity relative to cis,cis-muconate
-
-
?
3-Methyl-cis,cis-muconate
beta-Methylmuconolactone
-
at 5.6% of the activity relative to cis,cis-muconate
-
-
?
3-Methyl-cis,cis-muconate
beta-Methylmuconolactone
-
at 5.6% of the activity relative to cis,cis-muconate
-
-
?
cis,cis-hexadienedioate
2,5-dihydro-5-oxofuran-2-acetate
-
conversion of cis,cis-muconate to muconolactone, two proximal Lys residues exist in the active sites, which can potentially lead, via a single intermediate form, to the formation of either the syn- or anti-products. The enzyme from Mycobacterium smegmatis forms a syn-product, overview
-
-
r
cis,cis-hexadienedioate
2,5-dihydro-5-oxofuran-2-acetate
-
conversion of cis,cis-muconate to muconolactone, two proximal Lys residues exist in the active sites, which can potentially lead, via a single intermediate form, to the formation of either the syn- or anti-products. The enzyme from Pseudomonas fluorescens forms an anti-product, overview
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-
r
cis,cis-Muconate
(+)-Muconolactone
-
-
i.e. 5-oxo-2,5-dihydrofuran-2-acetate, , (4S)-muconolactone
?
cis,cis-Muconate
(+)-Muconolactone
-
no activity against trans-trans-muconate
-
-
?
cis,cis-Muconate
(+)-Muconolactone
-
-
-
-
?
cis,cis-Muconate
(+)-Muconolactone
-
i.e. cis,cis-2,4-hexadiendioate, , r
-
?
cis,cis-Muconate
(+)-Muconolactone
-
i.e. cis,cis-2,4-hexadiendioate, , r
-
-
?
cis,cis-muconate
(4S)-muconolactone
syn-cycloisomerization
-
-
?
cis,cis-Muconate
?
-
the enzyme plays a key role in the beta-ketoadipate pathway of benzoate degradation
-
-
?
cis,cis-Muconate
?
-
enzyme of the beta-ketoadipate pathway
-
-
?
cis,cis-Muconate
?
-
catalyzes the second step of the beta-ketoadipate pathway
-
-
?
cis,cis-Muconate
?
-
catalyzes the second step of the beta-ketoadipate pathway
-
-
?
cis,cis-muconate
muconolactone
-
the enzyme plays a crucial role in the bacterial degradation of aromatic compounds by converting cis,cis-muconate, the product of catechol ring cleavage to (4S)-muconolactone
-
?
cis,cis-muconate
muconolactone
-
different inducible production of MC I and MC II suggest that two catechol branches involved in the beta-ketoadipate pathway function in Frateuria sp. ANA-18
-
?
cis,cis-muconate
muconolactone
-
different inducible production of MC I and MC II suggest that two catechol branches involved in the beta-ketoadipate pathway function in Frateuria sp. ANA-18
-
?
cis,cis-muconate
muconolactone
-
i.e. cis,cis-hexadienedioate or (2Z,4Z)-hexa-2,4-dienedioate, in vitro activity
i.e. (2,5-dihydro-5-oxofuran-2-yl)acetate
-
?
cis,cis-muconate
muconolactone
-
i.e. cis,cis-hexadienedioate or (2Z,4Z)-hexa-2,4-dienedioate, in vitro activity
i.e. (2,5-dihydro-5-oxofuran-2-yl)acetate
-
?
cis,cis-muconate
muconolactone
-
the enzyme plays a crucial role in the bacterial degradation of aromatic compounds by converting cis,cis-muconate, the product of catechol ring cleavage to (4S)-muconolactone
-
?
cis,cis-muconate
muconolactone
-
the enzyme plays a crucial role in the bacterial degradation of aromatic compounds by converting cis,cis-muconate, the product of catechol ring cleavage to (4S)-muconolactone
-
?
cis,cis-muconate
muconolactone
-
enzyme is involved in beta-ketoadipate pathway
-
?
3-chloro-cis,cis-muconate
additional information
-
-
-
wild-type enzyme forms protoanemonin and 2-chloroprotoanemonin, mutant enzyme K169A forms cis-dienelactone and 2-chloro-cis-dienelactone
?
additional information
?
-
-
no activity with 3-chloro-cis,cis-muconate and 2,4-dichloro-cis,cis-muconate
-
?
additional information
?
-
-
no substrate: 2-chloro-cis,cis-muconate, 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
no substrate: 2-chloro-cis,cis-muconate, 2-fluoro-cis,cis-muconate
-
-
?
additional information
?
-
-
the enzyme is involved in degradation of 4-chlorobenzenesulfonic acid, 4CBSA, the major polar by-product of the chemical synthesis of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl) ethane, DDT, overview, 4-chlorobenzenesulfonic acid catabolic pathway, overview
-
-
?
additional information
?
-
-
the enzyme is involved in degradation of 4-chlorobenzenesulfonic acid, 4CBSA, the major polar by-product of the chemical synthesis of 1,1,1-trichloro-2,2-bis-(4-chlorophenyl) ethane, DDT, overview, 4-chlorobenzenesulfonic acid catabolic pathway, overview
-
-
?
additional information
?
-
-
no activity against 2-carboxy-cis,cis-muconate
-
-
?
additional information
?
-
-
the enzyme is a component of the beta-ketoadipate pathway
-
?
additional information
?
-
Pseudomonas putida A.3.12. / ATCC 12633
-
no activity against 2-carboxy-cis,cis-muconate
-
-
?
additional information
?
-
activity of the enzyme with muconate is negligible and at a substrate concentration of 0.1 mM substrate, the activity is only 0.4% of that with 3-chloromuconate, the enzyme is practically inactive with 2-chloromuconate
-
-
?
additional information
?
-
-
the methyl substitution at the C-2 position of muconate directs the cycloisomerization by 1,4-addition rather than 3,6-addition. The steric influence caused by methyl substitution may encourage the 1,4-cycloisomerization
-
?
additional information
?
-
-
the methyl substitution at the C-2 position of muconate directs the cycloisomerization by 1,4-addition rather than 3,6-addition. The steric influence caused by methyl substitution may encourage the 1,4-cycloisomerization
-
?
