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(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid + H2O
4-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
2-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
(2E,4E)-6-(3,4-dichlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3,4-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
(2E,4E)-6-(3,5-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3,5-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2,4-dihydroxypenta-2,4-dienoic acid
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-4-chloro-2-hydroxypenta-2,4-dienoic acid
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E,4Z)-5-chloro-2-hydroxypenta-2,4-dienoic acid
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2Z)-3-chloro-2-hydroxypenta-2,4-dienoic acid
2,6-dihydroxy-6-phenylhexa-2,4-dienoate
benzaldehyde + (2E)-2-hydroxypenta-2,4-dienoic acid
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
2-hydroxy-6-oxo-6-(2,3-dihydroxyphenyl)-hexa-2,4-dienoate + H2O
2,3-dihydroxybenzoate + 2-oxopent-4-enoate + H+
2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid + H2O
2-aminobenzoic acid + 2-hydroxypenta-2,4-dienoic acid
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O
2-oxopent-4-enoate + salicylate + H+
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)hexa-2,4-dienoate + H2O
2-oxopent-4-enoate + salicylate
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
benzoate + 2-hydroxypenta-2,4-dienoate
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
benzoate + 2-oxopent-4-enoate
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
2-hydroxypenta-2,4-dienoic acid + benzoate
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
?
-
i.e. HOPDA
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + 2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
3-isopropylcatechol + H2O
?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
3-[(7aR)-7a-hydroxy-1,5-dioxooctahydro-1H-inden-4-yl]propanoic acid + (2Z,4Z)-5-hydroxyhexa-2,4-dienoic acid
4-nitrophenyl benzoate + H2O
4-nitrophenol + benzoate
-
the serine nucleophile is activated by the His-Asp dyad
-
-
?
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid + H2O
2-hydroxypenta-2,4-dienoic acid + benzoate
biphenyl-2,3-diol + H2O
?
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate + H2O
benzoate + ethyl 2-(acetyloxy)penta-2,4-dienoate
-
-
-
-
?
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate + H2O
benzoate + ethyl-2-(acetyloxy)penta-2,4-dienoate
-
-
-
-
?
meta-ring fission intermediate + H2O
?
additional information
?
-
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid + H2O

4-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid + H2O
4-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid + H2O
4-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid + H2O
4-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O

benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O

2-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
2-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
2-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
2-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3,4-dichlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O

3,4-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3,4-dichlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3,4-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3,5-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O

3,5-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3,5-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3,5-dichlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O

3-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid + H2O
3-chlorobenzoate + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O

benzoate + (2E)-2,4-dihydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2,4-dihydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-2,4-dihydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O

benzoate + (2E)-4-chloro-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E)-4-chloro-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O

benzoate + (2E,4Z)-5-chloro-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2E,4Z)-5-chloro-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O

benzoate + (2Z)-3-chloro-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
benzoate + (2Z)-3-chloro-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
2,6-dihydroxy-6-phenylhexa-2,4-dienoate

benzaldehyde + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
2,6-dihydroxy-6-phenylhexa-2,4-dienoate
benzaldehyde + (2E)-2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O

benzoate + 2-oxopent-4-enoate
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
-
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
enzyme BphD catalyses the hydrolysis of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid, HOPDA, and many substrate analogues
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
enzyme BphD catalyses the hydrolysis of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid, HOPDA, and many substrate analogues
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
-
-
-
?
2,6-dioxo-6-phenylhexa-3-enoate + H2O
benzoate + 2-oxopent-4-enoate
enzyme BphD catalyses the hydrolysis of 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid, HOPDA, and many substrate analogues
-
-
?
2-hydroxy-6-oxo-6-(2,3-dihydroxyphenyl)-hexa-2,4-dienoate + H2O

2,3-dihydroxybenzoate + 2-oxopent-4-enoate + H+
-
-
enzyme is involved in metabolism of 2,2'-dihydroxybiphenyl
-
?
2-hydroxy-6-oxo-6-(2,3-dihydroxyphenyl)-hexa-2,4-dienoate + H2O
2,3-dihydroxybenzoate + 2-oxopent-4-enoate + H+
-
-
enzyme is involved in metabolism of 2,2'-dihydroxybiphenyl
-
?
2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid + H2O

2-aminobenzoic acid + 2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid + H2O
2-aminobenzoic acid + 2-hydroxypenta-2,4-dienoic acid
-
-
-
-
?
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O

2-oxopent-4-enoate + salicylate + H+
-
-
enzyme is involved in metabolism of 2,2'-dihydroxybiphenyl
-
?
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)-hexa-2,4-dienoate + H2O
2-oxopent-4-enoate + salicylate + H+
-
-
enzyme is involved in metabolism of 2,2'-dihydroxybiphenyl
-
?
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)hexa-2,4-dienoate + H2O

2-oxopent-4-enoate + salicylate
-
-
-
?
2-hydroxy-6-oxo-6-(2-hydroxyphenyl)hexa-2,4-dienoate + H2O
2-oxopent-4-enoate + salicylate
-
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O

benzoate + 2-hydroxypenta-2,4-dienoate
-
-
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
benzoate + 2-hydroxypenta-2,4-dienoate
-
-
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O

benzoate + 2-oxopent-4-enoate
-
-
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate + H2O
benzoate + 2-oxopent-4-enoate
-
-
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O

2-hydroxypenta-2,4-dienoic acid + benzoate
i.e. HOPDA, a biphenyl meta-cleavage product
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
2-hydroxypenta-2,4-dienoic acid + benzoate
i.e. HOPDA, a biphenyl meta-cleavage product
-
-
?
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid + H2O
2-hydroxypenta-2,4-dienoic acid + benzoate
i.e. HOPDA
-
-
?
3-isopropylcatechol + H2O

?
-
-
-
-
?
3-isopropylcatechol + H2O
?
-
-
-
-
?
3-methylcatechol + H2O

?
-
-
-
-
?
3-methylcatechol + H2O
?
-
-
-
-
?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O

3-[(7aR)-7a-hydroxy-1,5-dioxooctahydro-1H-inden-4-yl]propanoic acid + (2Z,4Z)-5-hydroxyhexa-2,4-dienoic acid
i.e. DSHA, a cholesterol meta-cleavage product
-
-
?
4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid + H2O
3-[(7aR)-7a-hydroxy-1,5-dioxooctahydro-1H-inden-4-yl]propanoic acid + (2Z,4Z)-5-hydroxyhexa-2,4-dienoic acid
i.e. DSHA, a cholesterol meta-cleavage product
-
-
?
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid + H2O

2-hydroxypenta-2,4-dienoic acid + benzoate
i.e. HOPODA, a HOPDA synthetic analogue
-
-
?
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid + H2O
2-hydroxypenta-2,4-dienoic acid + benzoate
i.e. HOPODA, a HOPDA synthetic analogue
-
-
?
biphenyl-2,3-diol + H2O

?
-
-
-
-
?
biphenyl-2,3-diol + H2O
?
-
-
-
-
?
catechol + H2O

?
-
-
-
-
?
catechol + H2O
?
-
-
-
-
?
meta-ring fission intermediate + H2O

?
-
catalysis of the hydrolytic C-C cleavage on phenylpropionic acid pathway
-
-
?
meta-ring fission intermediate + H2O
?
-
catalysis of the hydrolytic C-C cleavage on biphenyl degradation pathway
-
-
?
additional information

?
-
-
faint activity towards 2-hydroxy-6-oxohepta-2,4-dienoate and 2-hydroxymuconic semialdehyde
-
-
?
additional information
?
-
-
faint activity towards 2-hydroxy-6-oxohepta-2,4-dienoate and 2-hydroxymuconic semialdehyde
-
-
?
additional information
?
-
key role of non-active-site residue Met148 on the catalytic efficiency of meta-cleavage product hydrolase BphD
-
-
-
additional information
?
-
key role of non-active-site residue Met148 on the catalytic efficiency of meta-cleavage product hydrolase BphD
-
-
-
additional information
?
-
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
-
-
-
additional information
?
-
enzyme BphD accepts small alcohols such as methanol, ethanol, n-propanol and 2-propanol as nucleophiles in C-C bond cleavage of 2,6-dioxo-6-phenylhexa-3-enoate, thereby directly forming benzoate esters.Iin addition to the hydrolysis of C-C bonds, BphD also hydrolyses the ester bond in para-substituted nitrophenyl benzoates
-
-
-
additional information
?
-
-
enzyme is involved in the degradation of biphenyl
-
-
-
additional information
?
-
-
enzyme is involved in the degradation of biphenyl
-
-
-
additional information
?
-
-
6-acryl-2-hydroxy-6-ketohexa-2,4-dienoic acids synthesized as substrates for C-C hydrolase BphD
-
-
-
additional information
?
-
-
first total synthesis of meta ring fission intermediates, 6-acryl-2-hydroxy-6-ketohexa-2,4-dienoic acids synthesized as substrates for C-C hydrolase BphD
-
-
?
additional information
?
-
-
first total synthesis of meta ring fission intermediates, 6-acryl-2-hydroxy-6-ketohexa-2,4-dienoic acids synthesized as substrates for C-C hydrolase BphD
-
-
?
additional information
?
-
-
6-acryl-2-hydroxy-6-ketohexa-2,4-dienoic acids synthesized as substrates for C-C hydrolase BphD
-
-
-
additional information
?
-
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
-
-
-
additional information
?
-
enzyme BphD accepts small alcohols such as methanol, ethanol, n-propanol and 2-propanol as nucleophiles in C-C bond cleavage of 2,6-dioxo-6-phenylhexa-3-enoate, thereby directly forming benzoate esters.Iin addition to the hydrolysis of C-C bonds, BphD also hydrolyses the ester bond in para-substituted nitrophenyl benzoates
-
-
-
additional information
?
-
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
-
-
-
additional information
?
-
enzyme BphD accepts small alcohols such as methanol, ethanol, n-propanol and 2-propanol as nucleophiles in C-C bond cleavage of 2,6-dioxo-6-phenylhexa-3-enoate, thereby directly forming benzoate esters.Iin addition to the hydrolysis of C-C bonds, BphD also hydrolyses the ester bond in para-substituted nitrophenyl benzoates
-
-
-
additional information
?
-
-
enzyme is involved in the degradative pathway for dibenzofuran
-
-
-
additional information
?
-
-
enzyme is involved in the degradative pathway for dibenzofuran
-
-
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.00013 - 0.00065
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid
0.00019 - 0.00047
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.00033 - 0.0129
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
0.00075
(2E,4E)-6-(3,4-dichlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
0.00104
(2E,4E)-6-(3,5-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
0.00043 - 0.00046
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
0.00095 - 0.0044
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.0036 - 0.004
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.0049 - 0.018
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.00054 - 0.0069
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.00028 - 0.0051
2,6-dioxo-6-phenylhexa-3-enoate
0.0046
2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid
-
at 25°C
0.00071 - 0.00085
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
0.0002 - 0.008
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.31
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
pH 7.5, 25°C
0.0017 - 0.0373
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
0.002 - 0.077
meta-ring fission intermediate
-
additional information
additional information
-
0.00013
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid

-
-
0.00065
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid
-
-
0.00019
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
not chlorinated
0.00047
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
not chlorinated
0.00033
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid

-
-
0.0129
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
0.00043
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid

-
-
0.00046
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
0.00095
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
-
0.0044
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.0036
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
-
0.004
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.0049
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
-
0.018
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.00054
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
-
0.0069
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.00028
2,6-dioxo-6-phenylhexa-3-enoate

pH 7.0, 25°C, mutant M148D
0.00044
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148S
0.00047
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148W
0.00058
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148R
0.00074
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148H
0.00075
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, wild-type enzyme
0.00078
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148I
0.00079
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148T
0.00097
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148C
0.0012
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148K; pH 7.0, 25°C, mutant M148V
0.0013
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148Q
0.0014
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148E; pH 7.0, 25°C, mutant M148L; pH 7.0, 25°C, mutant M148N
0.0019
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148Y
0.003
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148P
0.0042
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148F
0.0049
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148G
0.0051
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148A
0.00071
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate

-
at 60°C
0.00085
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
-
at 25°C
0.0002
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
pH 7.5, 25°C, recombinant wild-type BphD, without methanol
0.0003
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
wild-type at 3.2°C
0.00085
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, with 494 mM methanol
0.002
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, with 12940 mM methanol
0.0028
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
S112C mutant at 25°C
0.008
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
pH 7.5, 25°C
0.0017
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate

-
mutant D237N
0.002
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
His6-BphD
0.0238
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
mutant H114A
0.037
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
mutant H265A
0.0373
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
mutant S112A
0.002
meta-ring fission intermediate

-
R188K; wild-type
-
0.004
meta-ring fission intermediate
-
N109A; N109H
-
0.0042
meta-ring fission intermediate
-
C261A
-
0.0068
meta-ring fission intermediate
-
wild-type
-
0.01
meta-ring fission intermediate
-
F173D
-
0.0282
meta-ring fission intermediate
-
R188Q
-
0.038
meta-ring fission intermediate
-
R188K
-
0.058
meta-ring fission intermediate
-
F173G
-
0.077
meta-ring fission intermediate
-
R188Q
-
additional information
additional information

-
values between 0.00013 and 0.00106 mM for processing of the 6-acryl-2-hydroxy-6-ketohexa-2,4-dienoic acid substrates
-
additional information
additional information
-
in the steady-state hydrolysis of HOPDA, kcat/Km values are independent of methanol concentration, while both kcat and Km values increase with methanol concentration, stopped-flow spectrophotometry and steady-state kinetics, overview
-
additional information
additional information
pre-steady-state kinetic burst of BphD
-
additional information
additional information
Michaelis-Menten steady-state kinetics, stopped-flow measurements
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
3.13 - 33.7
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid
4.18 - 7.6
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
1.74 - 2.1
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
29
(2E,4E)-6-(3,4-dichlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
11.2
(2E,4E)-6-(3,5-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
3.9 - 15.3
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
0.0055
(2E,4Z)-2,4-dihydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.00059
(2E,4Z)-4-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
1.03 - 1.53
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.0089 - 0.0172
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
0.13 - 9.9
2,6-dioxo-6-phenylhexa-3-enoate
1300
2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid
-
-
1.11
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate
-
at 60°C
0.066 - 26
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
6.3
4-nitrophenyl benzoate
-
pH 7.5, 25°C
0.33
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
pH 7.5, 25°C
0.0009 - 6.5
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
0.009 - 12
meta-ring fission intermediate
-
additional information
additional information
-
3.13
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid

-
-
33.7
(2E,4E)-2-hydroxy-6-(4-chlorophenyl)-6-oxohexa-2,4-dienoic acid
-
-
4.18
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
not chlorinated
7.6
(2E,4E)-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
not chlorinated
1.74
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid

-
-
2.1
(2E,4E)-6-(2-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
3.9
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid

-
-
15.3
(2E,4E)-6-(3-chlorophenyl)-2-hydroxy-6-oxohexa-2,4-dienoic acid
-
-
1.03
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
-
1.53
(2E,4Z)-5-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.0089
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

-
-
0.0172
(2Z,4E)-3-chloro-2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
-
0.13
2,6-dioxo-6-phenylhexa-3-enoate

pH 7.0, 25°C, mutant M148P
0.86
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148R
1.5
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148S; pH 7.0, 25°C, mutant M148Y
2.4
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148K
2.5
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148C
2.6
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148H
3.1
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148L
4.1
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148E
4.5
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148D
4.8
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148V
5.7
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148W
6.5
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148T
6.7
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148N
8
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148F
8.4
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148Q
9.4
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148G
9.5
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148I
9.6
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, wild-type enzyme
9.9
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148A
0.066
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

pH 7.5, 25°C
0.27
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
S112C mutant at 25°C
0.98
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
wild-type at 3.2°C
2 - 8
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, with 12940 mM methanol
6.5
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
wild-type at 25°C
6.5
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, without methanol
26
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, with 494 mM methanol
0.0009
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate

-
mutant S112A
0.0016
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
mutant H265A
0.028
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
mutant D237N
0.036
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
mutant H114A
6.5
ethyl-2-acetoxy-6-keto-6-phenylhexa-2,4-dienoate
-
His6-BphD
0.009
meta-ring fission intermediate

-
R188K
-
0.016
meta-ring fission intermediate
-
R188Q
-
0.08
meta-ring fission intermediate
-
N109H
-
0.1
meta-ring fission intermediate
-
R188Q
-
0.13
meta-ring fission intermediate
-
N109A
-
0.26
meta-ring fission intermediate
-
F173D
-
0.74
meta-ring fission intermediate
-
R188K
-
2 - 8
meta-ring fission intermediate
-
wild-type
-
6.5
meta-ring fission intermediate
-
wild-type
-
7.5
meta-ring fission intermediate
-
F173G
-
12
meta-ring fission intermediate
-
C261A
-
additional information
additional information

-
values between 0.88 and 5.85 s-1 for processing of the 6-acryl-2-hydroxy-6-ketohexa-2,4-dienoic acid substrates
-
additional information
additional information
-
in the steady-state hydrolysis of HOPDA, kcat/Km values are independent of methanol concentration, while both kcat and Km values increase with methanol concentration, stopped-flow spectrophotometry and steady-state kinetics, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
440 - 16100
2,6-dioxo-6-phenylhexa-3-enoate
9 - 32
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
1.1
8-(2-chlorophenyl)-2-hydroxy-5-methyl-6-oxoocta-2,4-dienoic acid
pH 7.5, 25°C
440
2,6-dioxo-6-phenylhexa-3-enoate

pH 7.0, 25°C, mutant M148P
780
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148Y
1490
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148R
1900
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148F
1920
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148G
1940
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148A
2000
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148K
2210
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148L
2610
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148C
2880
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148E
3500
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148S
3590
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148H
4000
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148V
4790
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148N
6460
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148Q
8240
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148T
12100
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148W
12200
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148I
12800
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, wild-type enzyme
16100
2,6-dioxo-6-phenylhexa-3-enoate
pH 7.0, 25°C, mutant M148D
9
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid

pH 7.5, 25°C
14
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, with 12940 mM methanol
31
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, with 494 mM methanol
32
2-Hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid
-
pH 7.5, 25°C, recombinant wild-type BphD, without methanol
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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M148A
site-directed mutagenesis of the non-active-site residue
M148C
site-directed mutagenesis of the non-active-site residue
M148D
site-directed mutagenesis of the non-active-site residue
M148E
site-directed mutagenesis of the non-active-site residue
M148F
site-directed mutagenesis of the non-active-site residue
M148G
site-directed mutagenesis of the non-active-site residue
M148H
site-directed mutagenesis of the non-active-site residue
M148I
site-directed mutagenesis of the non-active-site residue
M148K
site-directed mutagenesis of the non-active-site residue
M148L
site-directed mutagenesis of the non-active-site residue
M148N
site-directed mutagenesis of the non-active-site residue
M148P
site-directed mutagenesis of the non-active-site residue
M148Q
site-directed mutagenesis of the non-active-site residue
M148R
site-directed mutagenesis of the non-active-site residue
M148S
site-directed mutagenesis of the non-active-site residue
M148T
site-directed mutagenesis of the non-active-site residue
M148V
site-directed mutagenesis of the non-active-site residue
M148W
site-directed mutagenesis of the non-active-site residue
M148Y
site-directed mutagenesis of the non-active-site residue
M148A
-
site-directed mutagenesis of the non-active-site residue
-
M148D
-
site-directed mutagenesis of the non-active-site residue
-
M148L
-
site-directed mutagenesis of the non-active-site residue
-
M148P
-
site-directed mutagenesis of the non-active-site residue
-
M148W
-
site-directed mutagenesis of the non-active-site residue
-
C261A
-
2fold decreased turnover rate, Cys-261 seems to be not involved in catalysis
F173D
-
1.5fold increased Km value, 100fold decreased turnover rate
F173G
-
8fold increased Km value, 3.5fold decreased turnover rate
H114A
-
reduced activity, is able to accept the 6-phenyl-containing substrate, on a shorter time scale
H263A
-
overal structure similar, but asymmetry of the enzyme dimer more pronounced than for the native enzyme
N109A
-
similar Km value as wild-type, 200fold decreased turnover rate
N109H
-
similar Km value as wild-type, 350fold decreased turnover rate
R188K
-
5fold increased Km value,35fold decreased turnover rate
R188Q
-
first step of enzyme reaction, keto-enol tautomerization, becomes rate-limiting, 11fold increased Km value, 300fold decreased turnover rate
W264G
-
16fold increased Km value, 10fold decreased turnover rate
R190K
-
similar Km value as wild-type, 700fold decreased turnover rate
R190Q
-
14fold increased Km value, 400fold decreased turnover rate
S112A/H265Q
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme
S112C
-
lower enzyme activity
S114A

active site HsaD mutant, catalytically impaired and binds 4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid with an altered dissociation constant compared to the wild-type enzyme
S114A
-
active site HsaD mutant, catalytically impaired and binds 4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid with an altered dissociation constant compared to the wild-type enzyme
-
H265A

-
reduced activity
H265A
-
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme
H265Q

-
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme, rapid acylation of the variant during C-C bond cleavage suggesting that the serinate forms via a substrate-assisted mechanism in the reaction
H265Q
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme and does not show formation of the carbanion catalytic intermediate in contrast to the wild-type enzyme
S112A

-
reduced activity
S112A
-
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type enzyme
S114A

-
ca. 40fold reduction in activity for the His tagged mutant hydrolase relative to similar lysates of His-tagged native CarC
S114A
-
ca. 40fold reduction in activity for the His tagged mutant hydrolase relative to similar lysates of His-tagged native CarC
-
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Omori, T.; Sugimura, K.; Ishigooka, H.; Minoda, Y.
Purification and some propertiees of a 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid hydrolyzing enzyme from Pseudomonas cruciviae S93 B1 involved in the degradation of biphenyl
Agric. Biol. Chem.
50
931-937
1986
Pseudomonas cruciviae, Pseudomonas cruciviae S93 B1
-
brenda
Buenz, P.V.; Falchetto, R.; Cook, A.M.
Purification of two isofunctional hydrolases (EC 3.7.1.8) in the degradative pathway for dibenzofuran in Sphingomonas sp. strain RW1
Biodegradation
4
171-178
1993
Sphingomonas sp., Sphingomonas sp. RW1
brenda
Ahmad, S.; Fraser, J.; Sylvestre, M.; Larose, A.; Khan, A.; Bergeron, J.; Juteau, J.M.; Sondossi, M.
Sequence of the bphD gene encoding 2-hydroxy-6-oxo-(phenylchlorophenyl) hexa-2,4-dienoic acid (HOP/cPCA) hydrolase involved in the biphenyl/polychlorinated biphenyl degradation pathway in Comamonas testosteroni: evidence suggesting involvement of Ser112 in catalytic activity
Gene
156
69-74
1995
Comamonas testosteroni (Q59324)
brenda
Kim, E.; Kim, Y.; Kim, C.K.
Genetic structures of the genes encoding 2,3-dihydroxybiphenyl 1,2-dioxygenase and 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoic acid hydrolase from biphenyl- and 4-chlorobiphenyl-degrading Pseudomonas sp. strain DJ-12
Appl. Environ. Microbiol.
62
262-265
1996
Pseudomonas sp., Pseudomonas sp. DJ-12
brenda
Lau, P.C.K.; Garnon, J.; Labbe, D.; Wang, Y.
Location and sequence analysis of a 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase-encoding gene (bpdF) of the biphenyl polychlorinated biphenyl degradation pathway in Rhodococcus sp. M5
Gene
171
53-57
1996
Rhodococcus sp.
brenda
Horsman, G.P.; Ke, J.; Dai, S.; Seah, S.Y.; Bolin, J.T.; Eltis, L.D.
Kinetic and structural insight into the mechanism of BphD, a C-C bond hydrolase from the biphenyl degradation pathway
Biochemistry
45
11071-11086
2006
Paraburkholderia xenovorans
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, Paraburkholderia xenovorans
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, Paraburkholderia xenovorans
brenda
Speare, D.M.; Olf, P.; Bugg, T.D.
Hammett analysis of a C-C hydrolase-catalysed reaction using synthetic 6-aryl-2-hydroxy-6-ketohexa-2,4-dienoic acid substrates
Chem. Commun. (Camb. )
2002
2304-2305
2002
Pseudomonas sp., Pseudomonas sp. LB400
brenda
Seah, S.Y.; Labbe, G.; Kaschabek, S.R.; Reifenrath, F.; Reineke, W.; Eltis, L.D.
Comparative specificities of two evolutionarily divergent hydrolases involved in microbial degradation of polychlorinated biphenyls
J. Bacteriol.
183
1511-1516
2001
Rhodococcus globerulus, Rhodococcus globerulus P6
brenda
Seah, S.Y.; Labbe, G.; Nerdinger, S.; Johnson, M.R.; Snieckus, V.; Eltis, L.D.
Identification of a serine hydrolase as a key determinant in the microbial degradation of polychlorinated biphenyls
J. Biol. Chem.
275
15701-15708
2000
Burkholderia cepacia, Burkholderia cepacia LB400
brenda
Lim, J.; Lee, J.; Lim, J.; Min, K.R.; Kim, C.; Kim, Y.
Characterization of the pcbD gene encoding 2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase from Pseudomonas sp. P20
J. Microbiol. Biotechnol.
10
258-263
2000
Pseudomonas sp., Pseudomonas sp. P20
-
brenda
Nandhagopal, N.; Yamada, A.; Hatta, T.; Masai, E.; Fukuda, M.; Mitsui, Y.; Senda, T.
Crystal structure of 2-hydroxyl-6-oxo-6-phenylhexa-2,4-dienoic acid (HPDA) hydrolase (BphD enzyme) from the Rhodococcus sp. strain RHA1 of the PCB degradation pathway
J. Mol. Biol.
309
1139-1151
2001
Rhodococcus sp. (Q9KWQ6), Rhodococcus sp., Rhodococcus sp. RHA1 (Q9KWQ6)
brenda
Mukerjee-Dhar, G.; Shimura, M.; Miyazawa, D.; Kimbara, K.; Hatta, T.
bph genes of the thermophilic PCB degrader, Bacillus sp. JF8: characterization of the divergent ring-hydroxylating dioxygenase and hydrolase genes upstream of the Mn-dependent BphC
Microbiology
151
4139-4151
2005
Bacillus sp. (in: Bacteria), Bacillus sp. (in: Bacteria) JF8
brenda
Speare, D.M.; Fleming, S.M.; Beckett, M.N.; Li, J.J.; Bugg, T.D.
Synthetic 6-aryl-2-hydroxy-6-ketohexa-2,4-dienoic acid substrates for C-C hydrolase BphD: investigation of a general base catalytic mechanism
Org. Biomol. Chem.
2
2942-2950
2004
Pseudomonas sp., Pseudomonas sp. LB400
brenda
Riddle, R.R.; Gibbs, P.R.; Willson, R.C.; Benedik, M.J.
Purification and properties of 2-hydroxy-6-oxo-6-(2-aminophenyl)hexa-2,4-dienoic acid hydrolase involved in microbial degradation of carbazole
Protein Expr. Purif.
28
182-189
2003
Pseudomonas sp., Pseudomonas sp. LD2
brenda
Lack, N.; Yam, K.; Lowe, E.; Horsman, G.; Owen, R.; Sim, E.; Eltis, L.
Characterization of a carbon-carbon hydrolase from Mycobacterium tuberculosis involved in cholesterol metabolism
J. Biol. Chem.
285
434-443
2010
Mycobacterium tuberculosis (P9WNH5), Mycobacterium tuberculosis H37Rv (P9WNH5)
brenda
Ruzzini, A.C.; Horsman, G.P.; Eltis, L.D.
The catalytic serine of MCP hydrolases is activated differently for C-O bond cleavage than for C-C bond cleavage
Biochemistry
51
5831-5840
2012
Paraburkholderia xenovorans
brenda
Ruzzini, A.C.; Ghosh, S.; Horsman, G.P.; Foster, L.J.; Bolin, J.T.; Eltis, L.D.
Identification of an acyl-enzyme intermediate in a meta-cleavage product hydrolase reveals the versatility of the catalytic triad
J. Am. Chem. Soc.
134
4615-4624
2012
Paraburkholderia xenovorans (P47229)
brenda
Kohler, H.P.; Schmid, A.; van der Maarel, M.
Metabolism of 2,2'-dihydroxybiphenyl by Pseudomonas sp. strain HBP1: production and consumption of 2,2',3-trihydroxybiphenyl
J. Bacteriol.
175
1621-8
1993
Pseudomonas sp., Pseudomonas sp. HBP1
brenda
Siirola, E.; Frank, A.; Grogan, G.; Kroutil, W.
C-C hydrolases for biocatalysis
Adv. Synth. Catal.
355
1677-1691
2013
Paraburkholderia xenovorans (P47229), Rhodococcus sp. (Q75WN8), Rhodococcus sp. RHA1 (Q75WN8)
-
brenda
Zhou, H.; Qu, Y.; Kong, C.; Shen, E.; Wang, J.; Zhang, X.; Ma, Q.; Zhou, J.
The key role of a non-active-site residue Met148 on the catalytic efficiency of meta-cleavage product hydrolase BphD
Appl. Microbiol. Biotechnol.
97
10399-10411
2013
Dyella ginsengisoli (B5SU85), Dyella ginsengisoli LA-4 (B5SU85)
brenda
Li, Y.; Zhang, R.; Du, L.; Zhang, Q.; Wang, W.
Insight into the catalytic mechanism of meta-cleavage product hydrolase BphD: a quantum mechanics/molecular mechanics study
RSC Adv.
5
66591-66597
2015
Paraburkholderia xenovorans
-
brenda