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Literature summary for 5.5.1.1 extracted from

  • Vollmer, M.D.; Hoier, H.; Hecht, H.J.; Schell, U.; Groning, J.; Goldman, A.; Schlomann, M.
    Substrate specificity of and product formation by muconate cycloisomerases: an analysis of wild-type enzymes and engineered variants (1998), Appl. Environ. Microbiol., 64, 3290-3299.
    View publication on PubMedView publication on EuropePMC

Protein Variants

Protein Variants Comment Organism
A271S ratio of turnover number to Km-value: 1.5fold decrease with cis,cis-muconate as substrate, 3.3fold decrease with 2-chloro-cis,cis-muconate as substrate, 27fold increase with 3-chloro-cis,cis-muconate as substrate, 1.9fold decrease with 2,4-dichloro-cis,cis-muconate as substrate, 1.5fold decrease with 3-fluoro-cis,cis-muconate as substrate, 1.1fold increase with 2-methyl-cis,cis-muconate as substrate, 1.1fold decrease with 3-methyl-cis,cis-muconate as substrate Pseudomonas putida
F329I ratio of turnover number to Km-value: 5.7fold decrease with cis,cis-muconate as substrate, 1.6fold increase with 2-chloro-cis,cis-muconate as substrate, 3.4fold increase with 3-chloro-cis,cis-muconate as substrate, 3.2fold increase with 2,4-dichloro-cis,cis-muconate as substrate, 1.7fold decrease with 3-fluoro-cis,cis-muconate as substrate, 1.5fold increase with 2-methyl-cis,cis-muconate as substrate, 5.8fold decrease with 3-methyl-cis,cis-muconate as substrate Pseudomonas putida
I54V ratio of turnover number to Km-value: 11.9fold decrease with cis,cis-muconate as substrate, nearly identical to wild-type value with 2-chloro-cis,cis-muconate and 3-methyl-cis,cis-muconate as substrate, 22fold increase with 3-chloro-cis,cis-muconate as substrate, 1.67fold decrease with 2,4-dichloro-cis,cis-muconate as substrate, 5.8fold decrease with 3-fluoro-cis,cis-muconate as substrate, 8.8fold decrease with 2-methyl-cis,cis-muconate as substrate Pseudomonas putida
I54V/F329I ratio of turnover number to Km-value: 81.5fold decrease with cis,cis-muconate as substrate, 2.6fold decrease with 2-chloro-cis,cis-muconate as substrate, 2.7fold increase with 3-chloro-cis,cis-muconate as substrate, 3.8fold increase with 2,4-dichloro-cis,cis-muconate as substrate, 2fold decrease with 3-fluoro-cis,cis-muconate as substrate, 4fold decrease with 2-methyl-cis,cis-muconate as substrate, 2fold decrease with 3-methyl-cis,cis-muconate as substrate Pseudomonas putida
K276N ratio of turnover number to Km-value: 10.7fold decrease with cis,cis-muconate as substrate, 8.7fold decrease with 2-chloro-cis,cis-muconate as substrate, 3.5fold increase with 3-chloro-cis,cis-muconate as substrate, 8.7fold decrease with 2,4-dichloro-cis,cis-muconate as substrate, 4.1fold decrease with 3-fluoro-cis,cis-muconate as substrate, 16.7fold decrease with 2-methyl-cis,cis-muconate as substrate, 12.1fold decrease with 3-methyl-cis,cis-muconate as substrate Pseudomonas putida
L333V ratio of turnover number to Km-value: 238fold decrease with cis,cis-muconate as substrate, 41.5fold decrease with 2-chloro-cis,cis-muconate as substrate, 3.4fold increase with 3-chloro-cis,cis-muconate as substrate, 5.9fold decrease with 2,4-dichloro-cis,cis-muconate as substrate, 1.4fold decrease with 3-fluoro-cis,cis-muconate as substrate, 34.6fold decrease with 2-methyl-cis,cis-muconate as substrate, 16.5fold decrease with 3-methyl-cis,cis-muconate as substrate Pseudomonas putida
Y59W ratio of turnover number to Km-value: 12.9fold decrease with cis,cis-muconate as substrate, nearly identical to wild-type value with 2-chloro-cis,cis-muconate as substrate, 4.4fold decrease with 3-fluoro-cis,cis-muconate, 1.8fold decrease with 2-methyl-cis,cis-muconate as substrate, 10.2fold decrease with 3-methyl-cis,cis-muconate as substrate Pseudomonas putida

Inhibitors

Inhibitors Comment Organism Structure
2,4-dichloro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Acinetobacter calcoaceticus
2,4-dichloro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Pseudomonas putida
2-fluoro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Acinetobacter calcoaceticus
2-fluoro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Pseudomonas putida
3-chloro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Pseudomonas putida

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.006
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.0064
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S or I54V/F329 Pseudomonas putida
0.0072
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.0091
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.0097
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
0.012
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.015
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
0.016
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
0.017
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
0.026
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.033
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
0.034
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.035
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
0.036
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.037
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
0.039
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.04
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.04
-
cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.04
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.044
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
0.045
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.045
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
0.047
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.047
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W and F329I Pseudomonas putida
0.052
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.057
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S or I54V/F329 Pseudomonas putida
0.058
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.059
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
0.059
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.06
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
0.063
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.068
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
0.069
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
0.074
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.074
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.076
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.078
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
0.093
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.096
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
0.097
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.099
-
3-methyl-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
0.1
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
0.1
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S or I54V/F329 Pseudomonas putida
0.11
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
0.13
-
cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
0.14
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
0.15
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
0.15
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
0.18
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
0.18
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.21
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
0.23
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.29
-
2-chloro-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
0.32
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
0.49
-
2-methyl-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
0.55
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
0.69
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
cis,cis-muconate Pseudomonas putida 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 muconolactone
-
?
cis,cis-muconate Acinetobacter calcoaceticus 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 muconolactone
-
?
cis,cis-muconate Pseudomonas putida PRS2000 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 muconolactone
-
?

Organism

Organism UniProt Comment Textmining
Acinetobacter calcoaceticus
-
-
-
Pseudomonas putida
-
PRS2000
-
Pseudomonas putida PRS2000
-
PRS2000
-

Purification (Commentary)

Purification (Comment) Organism
-
Pseudomonas putida
-
Acinetobacter calcoaceticus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2,4-dichloro-cis,cis-muconate
-
Pseudomonas putida ?
-
?
2,4-dichloro-cis,cis-muconate
-
Pseudomonas putida PRS2000 ?
-
?
2-Chloro-cis,cis-muconate
-
Acinetobacter calcoaceticus ?
-
?
2-chloro-cis,cis-muconate
-
Pseudomonas putida (+)-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 ?
2-Methyl-cis,cis-muconate
-
Acinetobacter calcoaceticus ?
-
?
2-methyl-cis,cis-muconate
-
Pseudomonas putida 2-methylmuconolactone
-
?
3-chloro-cis,cis-muconate
-
Pseudomonas putida protoanemonin + ? formed by wild-type enzyme and mutant enzymes I54V, A271S, K276N, F329I, L333V, I54V/F329I ?
3-Fluoro-cis,cis-muconate
-
Pseudomonas putida ?
-
?
3-Fluoro-cis,cis-muconate
-
Acinetobacter calcoaceticus ?
-
?
3-Fluoro-cis,cis-muconate
-
Pseudomonas putida PRS2000 ?
-
?
3-Methyl-cis,cis-muconate
-
Pseudomonas putida ?
-
?
3-Methyl-cis,cis-muconate
-
Acinetobacter calcoaceticus ?
-
?
3-Methyl-cis,cis-muconate
-
Pseudomonas putida PRS2000 ?
-
?
cis,cis-muconate
-
Pseudomonas putida muconolactone
-
?
cis,cis-muconate
-
Acinetobacter calcoaceticus muconolactone
-
?
cis,cis-muconate 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 Pseudomonas putida muconolactone
-
?
cis,cis-muconate 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 Acinetobacter calcoaceticus muconolactone
-
?
cis,cis-muconate
-
Pseudomonas putida PRS2000 muconolactone
-
?
cis,cis-muconate 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 Pseudomonas putida PRS2000 muconolactone
-
?
additional information no activity with 3-chloro-cis,cis-muconate and 2,4-dichloro-cis,cis-muconate Acinetobacter calcoaceticus ?
-
?

Synonyms

Synonyms Comment Organism
ADP1
-
Acinetobacter calcoaceticus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.4
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
3.4
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
36.6
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
43.8
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
52.8
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
174
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
192
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
198
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
432
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
600
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
900
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W and A271S Pseudomonas putida
1020
-
2-chloro-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
1320
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
1920
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
2100
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
2880
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
2940
-
2-chloro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
3120
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
3240
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
3840
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
4080
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
5700
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
6600
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
8400
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
12000
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
16200
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
18600
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S or I54V/F329 Pseudomonas putida
19200
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
22800
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
27600
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
32400
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
35400
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
39000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
40800
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
44400
-
3-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
57600
-
3-chloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
66000
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
72000
-
2,4-dichloro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
84000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S or I54V/F329 Pseudomonas putida
108000
-
3-methyl-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
126000
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
150000
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V Pseudomonas putida
156000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
156000
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
192000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
202000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
222000
-
cis,cis-muconate pH 7.5, 25°C Acinetobacter calcoaceticus
222000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme Y59W Pseudomonas putida
234000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
246000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme L333V Pseudomonas putida
294000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme I54V/F329I Pseudomonas putida
304000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
312000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N Pseudomonas putida
360000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
426000
-
cis,cis-muconate pH 7.5, 25°C, mutant enzyme A271S Pseudomonas putida
480000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, mutant enzyme F329I Pseudomonas putida
534000
-
3-fluoro-cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida
600000
-
2-methyl-cis,cis-muconate pH 7.5, 25°C, mutant enzyme K276N or F329I Pseudomonas putida
756000
-
cis,cis-muconate pH 7.5, 25°C, wild-type enzyme Pseudomonas putida

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.0035
-
2,4-dichloro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Pseudomonas putida
0.027
-
2-fluoro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Acinetobacter calcoaceticus
0.031
-
2-fluoro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Pseudomonas putida
0.035
-
2,4-dichloro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Acinetobacter calcoaceticus
0.095
-
3-chloro-cis,cis-muconate inhibitor of cis,cis-muconate conversion Pseudomonas putida