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(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + succinate
(2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + fumarate
(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + succinate
(1)
-
-
-
(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + succinate
a catalytic mechanism is proposed involving stabilisation of reactive intermediates and activation of a nucleophilic water molecule by Ser110
(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + succinate
although MCP hydrolases have a catalytic serine in the active site, the mechanism proceeds via a geminal diol, rather than an acyl-enzyme intermediate, reaction mechanism of the hydrolysis reaction, overview. MCP hydrolases accept alternative nucleophiles in addition to water, and accepts hydroxylamine in the C-C cleavage reaction. MhpC has a typical serine-hydrolase catalytic triad (Ser107, Asp228 and His256), but mechanistic studies indicate that the serine in the active site does not act as a nucleophile in the hydrolysis, but rather the reaction proceeds via general base catalysis.The serine in the active site might stabilise the oxyanion intermediate by hydrogen bonding
(2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + fumarate
(2)
-
-
-
(2Z,4E,7E)-2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate + H2O = (2Z)-2-hydroxypenta-2,4-dienoate + fumarate
a catalytic mechanism is proposed involving stabilisation of reactive intermediates and activation of a nucleophilic water molecule by Ser110
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(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O
(2Z)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme also catalyses the reverse reaction of C-C hydrolysis, namely C-C bond formation
Products: -
r
2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid + H2O
?
-
Substrates: MhpC mutant is able to accept the 2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid, on a shorter time scale
Products: -
?
additional information
?
-
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: -
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: -
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme is involved catabolism of 3-(3-hydroxyphenyl)propionate
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: -
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
additional information
?
-
Substrates: MCP hydrolases catalyse the C-C bond cleavage of compounds with a common structure, 2-hydroxy-6-oxohexa-2,4-dienoate with different substituents at the C-6 carbon
Products: -
?
additional information
?
-
Substrates: the enzyme is able to catalyse carbon-carbon bond formation. In addition to its natural substrate 2-hydroxy-6-oxonona-1,9-dienedioic acid, enzyme MhpC also hydrolyses various analogues and also the hydrolysis of ester bonds of monoethyl adipate and 4-nitrophenyl valerate. The H114A mutant of the enzyme also hydrolyses 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid, HOPDA, a substrate of enzyme BphD, EC 3.7.1.8. Incubation of monomethyl succinate and ethyl 2-hydroxypentadienoate with the wild-type freeze-dried MhpC in hexane result in C-C bond formation product
Products: -
?
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(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
(2Z,4E)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + H2O
(2Z)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme also catalyses the reverse reaction of C-C hydrolysis, namely C-C bond formation
Products: -
r
additional information
?
-
Substrates: MCP hydrolases catalyse the C-C bond cleavage of compounds with a common structure, 2-hydroxy-6-oxohexa-2,4-dienoate with different substituents at the C-6 carbon
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme is involved catabolism of 3-(3-hydroxyphenyl)propionate
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate + H2O
(2E)-2-hydroxypenta-2,4-dienoate + succinate
-
Substrates: the enzyme is involved in 3-phenylpropanoate catabolism
Products: -
?
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0.0012 - 0.125
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
0.0238
2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid
-
pH 8.0, 25Ā°C
0.0012
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S40A
0.0025
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme H114A
0.004
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme N109A
0.004
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme N109H
0.0042
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme C261A
0.0055
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme H263A
0.0068
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, wild-type enzyme
0.0068
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°, wild-type enzyme
0.01
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme F173D
0.0175
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S110G
0.0185
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S110A
0.038
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme R188K
0.058
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme F173G
0.077
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme R188Q
0.125
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme W264G
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0.001 - 12
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
0.036
2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid
-
pH 8.0, 25Ā°C
0.001
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S110G
0.0029
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme H263A
0.0054
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S110A
0.016
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme D235A, approximate value from activity of the cell extract
0.08
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme N109H
0.1
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme R188Q
0.13
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme N109A
0.26
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme F173D
0.74
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme R188K
2 - 8
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, wild-type enzyme
2 - 8
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°, wild-type enzyme
2.7
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme W264G
2.9
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S40A
4.5
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme H114A
7.5
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme F173G
12
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme C261A
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0.057 - 4118
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
1.51
2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid
-
pH 8.0, 25Ā°C
0.057
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S110G
0.29
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S110A
1.4
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme R188Q
5.27
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme H263A
19
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme N109H
19
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme R188K
21
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme W264G
26
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme F173D
33
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme N109A
130
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme F173G
242
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme S40A
412
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, wild-type enzyme
1800
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme H114A
2900
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°C, mutant enzyme C261A
4118
(2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
pH 8.0, 25Ā°, wild-type enzyme
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C261A
1.4fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
F173D
158fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
F173G
32fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
H263A
mutant exhibits very slow ketonisation and C-C cleavage
N109A
125fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
N109H
217fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
R188K
217fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
R188Q
2941fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
S110A
exhibits fast ketonisation, an intermediate phase, and slow C-C cleavage
S110G
exhibits fast ketonisation, an intermediate phase, and slow C-C cleavage
S40A
shows twofold reduced catalytic efficiency, but shows a very fast interconversion of dienol to dienolate forms of the substrate
W264G
196fold decrease in kcat/Km for (2E,4Z)-2-hydroxy-6-oxonona-2,4-dienedioate
H114A
-
MhpC mutant is able to accept the 2-hydroxy-6-keto-6-phenylhexa-2,4-dienoic acid, on a shorter time scale
H114A
shows twofold-reduced catalytic efficiency, ruling out a catalytic role, but shows a fivefold-reduced KM for the natural substrate, and an ability to process an aryl-containing substrate, implying a role for His114 in positioning of the substrate
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Burlingame, R.; Chapmen, P.J.
Catabolism of phenylpropionic acid and its 3-hydroxy-derivative by Escherichia coli
J. Bacteriol.
155
113-121
1983
Escherichia coli
brenda
Burlingame, R.P.; Wyman, L.; Chapman, P.J.
Isolation and characterization of Escherichia coli mutants defective for phenylpropionate degradation
J. Bacteriol.
168
55-64
1986
Escherichia coli
brenda
Diaz, E.; Ferrandez, A.; Garcia, J.L.
Characterization of the hca cluster encoding the dioxygenolytic pathway for initial catabolism of 3-phenylpropionic acid in Escherichia coli K-12
J. Bacteriol.
180
2915-2923
1998
Escherichia coli (P0ABW0)
brenda
Li, J.J.; Li, C.; Blindauer, C.A.; Bugg, T.D.
Evidence for a gem-diol reaction intermediate in bacterial C-C hydrolase enzymes BphD and MhpC from 13C NMR spectroscopy
Biochemistry
45
12461-12469
2006
Escherichia coli
brenda
Li, C.; Li, J.J.; Montgomery, M.G.; Wood, S.P.; Bugg, T.D.
Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD
Biochemistry
45
12470-12479
2006
Escherichia coli (P77044)
brenda
Ferrandez, A.; Garcia, J.L.; Diaz, E.
Genetic characterization and expression in heterologous hosts of the 3-(3-hydroxyphenyl)propionate catabolic pathway of Escherichia coli K-12
J. Bacteriol.
179
2573-2581
1997
Escherichia coli (P77044)
brenda
Li, C.; Montgomery, M.G.; Mohammed, F.; Li, J.J.; Wood, S.P.; Bugg, T.D.
Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants
J. Mol. Biol.
346
241-251
2005
Escherichia coli (P77044)
brenda
Dunn, G.; Montgomery, M.G.; Mohammed, F., Coker, A.; Cooper, J.B.; Robertson, T.; Garcia, J.L.; Bugg, T.D.; Wood, S.P.
The structure of the C-C bond hydrolase MhpC provides insights into its catalytic mechanism
J. Mol. Biol.
346
253-265
2005
Escherichia coli (P77044), Escherichia coli
brenda
Siirola, E.; Frank, A.; Grogan, G.; Kroutil, W.
C-C hydrolases for biocatalysis
Adv. Synth. Catal.
355
1677-1691
2013
Escherichia coli (P77044)
-
brenda
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