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1,4-dihydroxy-2-naphthoate + O2
?
1-hydroxy-2-naphthoate + O2
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
3,4-dichlorosalicylate + O2
?
3,4-dimethylgentisate + O2
?
3,5-dibromosalicylate + O2
?
3,6-dichlorogentisate + O2
?
3-aminosalicylate + O2
(2E,4Z)-2-amino-6-oxohepta-2,4-dienoate
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
3-bromosalicylate + O2
(2E,4Z)-2-bromo-6-oxohepta-2,4-dienoate
low activity
-
-
?
3-bromosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3-chlorogentisate + O2
3-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-chlorosalicylate + O2
(2E,4Z)-2-chloro-6-oxohepta-2,4-dienoate
low activity
-
-
?
3-chlorosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3-ethylgentisate + O2
3-ethyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
3-hydroxybenzoate + O2
3,4-dihydroxy-6-oxo-hepta-2,4-dienedioic acid
3-hydroxysalicylate + O2
(2E,4Z)-2-hydroxy-6-oxohepta-2,4-dienoate
low activity
-
-
?
3-hydroxysalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3-isopropyl-gentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
3-isopropylgentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
3-methylgentisate + O2
3-methyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
Vmax is 10.1% of Vmax for gentisate
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
3-methylsalicylate + O2
(2Z,4Z)-2-methyl-6-oxohepta-2,4-dienoate
low activity
-
-
?
3-methylsalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3-O-methylgentisate + O2
?
4-aminosalicylate + O2
(2Z,4E)-3-amino-6-oxohepta-2,4-dienoate
-
-
-
?
4-bromosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
4-chlorogentisate + O2
2-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
4-chlorosalicylate + O2
(2Z,4E)-3-chloro-6-oxohepta-2,4-dienoate
low activity
-
-
?
4-chlorosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
4-fluorogentisate + O2
2-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
4-hydroxysalicylate + O2
(2Z,4E)-3-hydroxy-6-oxohepta-2,4-dienoate
low activity
-
-
?
4-hydroxysalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
4-isopropylgentisate + O2
4-hydroxy-2-isopropyl-6-oxo-hepta-2,4-dienedioic acid
4-methylgentisate + O2
4-hydroxy-2-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-methylgentisate + O2
4-hydroxy-2-methyl-6-oxo-hepta-2,4-dienedioic acid
4-methylsalicylate + O2
(2Z,4Z)-3-methyl-6-oxohepta-2,4-dienoate
low activity
-
-
?
4-methylsalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
4-O-methylgentisate + O2
?
5-aminosalicylate + O2
(2Z,4E)-4-amino-6-oxohepta-2,4-dienedioate
5-bromosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
5-chlorosalicylate + O2
(2Z,4E)-4-chloro-6-oxohepta-2,4-dienoate
low activity
-
-
?
5-chlorosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
5-fluorosalicylate + O2
(2Z,4E)-4-fluoro-6-oxohepta-2,4-dienoate
low activity
-
-
?
5-fluorosalicylate + O2
?
5-methylsalicylate + O2
(2Z,4Z)-4-methyl-6-oxohepta-2,4-dienoate
low activity
-
-
?
5-methylsalicylate + O2
?
benzoate + O2
3-hydroxy-6-oxoheptadienoic acid
-
-
-
-
?
cinnamate + O2
?
-
-
-
-
?
gentisate + O2
maleylpyruvate
phenylpropionate + O2
?
-
-
-
-
?
salicylate + O2
(2Z,4Z)-6-oxohepta-2,4-dienoate
-
-
-
?
salicylate + O2
2-oxohepta-3,5-dienedioic acid
salicylate + O2
?
-
-
-
-
?
additional information
?
-
1,4-dihydroxy-2-naphthoate + O2

?
-
-
-
-
?
1,4-dihydroxy-2-naphthoate + O2
?
-
-
-
-
?
1,4-dihydroxy-2-naphthoate + O2
?
-
-
-
?
1,4-dihydroxy-2-naphthoate + O2
?
-
-
-
?
1-hydroxy-2-naphthoate + O2

?
-
-
-
-
?
1-hydroxy-2-naphthoate + O2
?
-
-
-
-
?
1-hydroxy-2-naphthoate + O2
?
weak activity
-
-
?
1-hydroxy-2-naphthoate + O2
?
weak activity
-
-
?
2,5-dihydroxybenzoate + O2

maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
the enzyme is highly specific for 2,5-dihydroxybenzoate
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
the enzyme is highly specific for 2,5-dihydroxybenzoate
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
the enzyme is involbved in the 3-phenylpropionic acid deg´radation pathway
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
ir
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
ir
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
i.e. gentisate
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
i.e. gentisate
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
i.e. gentisate
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
i.e. gentisate
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
i.e. gentisic acid
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
ir
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
ir
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
ir
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-dihydroxybenzoate + O2
maleylpyruvate
-
-
-
?
2,5-xylenol + O2

?
-
-
-
-
?
2,5-xylenol + O2
?
-
-
-
-
?
3,4-dichlorosalicylate + O2

?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3,4-dichlorosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3,4-dimethylgentisate + O2

?
-
-
-
-
?
3,4-dimethylgentisate + O2
?
-
-
-
-
?
3,5-dibromosalicylate + O2

?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3,5-dibromosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3,6-dichlorogentisate + O2

?
-
-
-
-
?
3,6-dichlorogentisate + O2
?
-
-
-
-
?
3-aminosalicylate + O2

(2E,4Z)-2-amino-6-oxohepta-2,4-dienoate
-
-
-
?
3-aminosalicylate + O2
(2E,4Z)-2-amino-6-oxohepta-2,4-dienoate
-
-
-
?
3-aminosalicylate + O2

?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3-aminosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
3-bromogentisate + O2

3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
Vmax is 48.5% of Vmax for gentisate
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-bromogentisate + O2
3-bromo-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-ethylgentisate + O2

3-ethyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-ethylgentisate + O2
3-ethyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-ethylgentisate + O2
3-ethyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-ethylgentisate + O2
3-ethyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
Vmax is 39.7% of Vmax for gentisate
-
-
?
3-ethylgentisate + O2
3-ethyl-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
Vmax is 39.7% of Vmax for gentisate
-
-
?
3-fluorogentisate + O2

3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
Vmax of recombinant enzyme is 20.5% higher compared to gentisate
-
-
?
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-fluorogentisate + O2
3-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
Vmax of recombinant enzyme is 20.5% higher compared to gentisate
-
-
?
3-hydroxybenzoate + O2

3,4-dihydroxy-6-oxo-hepta-2,4-dienedioic acid
-
minor pathway
-
-
?
3-hydroxybenzoate + O2
3,4-dihydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-hydroxybenzoate + O2
3,4-dihydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-hydroxybenzoate + O2
3,4-dihydroxy-6-oxo-hepta-2,4-dienedioic acid
-
main pathway
-
-
?
3-hydroxybenzoate + O2
3,4-dihydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-hydroxybenzoate + O2

?
-
-
-
-
?
3-hydroxybenzoate + O2
?
-
-
-
-
?
3-isopropyl-gentisate + O2

4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropyl-gentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropyl-gentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropyl-gentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropylgentisate + O2

4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropylgentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropylgentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-isopropylgentisate + O2
4-hydroxy-3-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
Vmax is 57.1% of Vmax for gentisate
-
-
?
3-methylgentisate + O2

4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-methylgentisate + O2
4-hydroxy-3-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
3-O-methylgentisate + O2

?
-
-
-
-
?
3-O-methylgentisate + O2
?
-
-
-
-
?
4-chlorogentisate + O2

2-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-chlorogentisate + O2
2-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-chlorogentisate + O2
2-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-chlorogentisate + O2
2-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-chlorogentisate + O2
2-chloro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-fluorogentisate + O2

2-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-fluorogentisate + O2
2-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-fluorogentisate + O2
2-fluoro-4-hydroxy-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-hydroxybenzoate + O2

?
-
-
-
-
?
4-hydroxybenzoate + O2
?
-
-
-
-
?
4-isopropylgentisate + O2

4-hydroxy-2-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-isopropylgentisate + O2
4-hydroxy-2-isopropyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-methylgentisate + O2

4-hydroxy-2-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-methylgentisate + O2
4-hydroxy-2-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-methylgentisate + O2
4-hydroxy-2-methyl-6-oxo-hepta-2,4-dienedioic acid
-
-
-
-
?
4-O-methylgentisate + O2

?
-
-
-
-
?
4-O-methylgentisate + O2
?
-
-
-
-
?
5-aminosalicylate + O2

(2Z,4E)-4-amino-6-oxohepta-2,4-dienedioate
-
-
-
?
5-aminosalicylate + O2
(2Z,4E)-4-amino-6-oxohepta-2,4-dienedioate
-
-
-
?
5-aminosalicylate + O2

?
-
-
-
?
5-aminosalicylate + O2
?
-
-
-
?
5-aminosalicylate + O2
?
-
-
-
-
?
5-aminosalicylate + O2
?
-
a gentisate 1,2-dioxygenase with an extremely relaxed substrate specificity is responsible for the unusual oxidation of salicylate by Pseudoaminobacter salicylatoxidans BN12. Relative activities with salicylate, 5-aminosalicylate, 1-hydroxy-2-naphthoate, and gentisate with both preparations are about 1:10:40:120
-
-
?
5-aminosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
5-aminosalicylate + O2
?
-
-
-
-
?
5-aminosalicylate + O2
?
-
a gentisate 1,2-dioxygenase with an extremely relaxed substrate specificity is responsible for the unusual oxidation of salicylate by Pseudoaminobacter salicylatoxidans BN12. Relative activities with salicylate, 5-aminosalicylate, 1-hydroxy-2-naphthoate, and gentisate with both preparations are about 1:10:40:120
-
-
?
5-aminosalicylate + O2
?
-
kcat/KM is less than 1% of the kcat/Km for gentisate
-
-
?
5-aminosalicylate + O2
?
partly preferred substrate
-
-
?
5-aminosalicylate + O2
?
partly preferred substrate
-
-
?
5-fluorosalicylate + O2

?
-
-
-
?
5-fluorosalicylate + O2
?
-
-
-
?
5-fluorosalicylate + O2
?
-
-
-
-
?
5-fluorosalicylate + O2
?
-
kcat/KM is 1.4% of the kcat/Km for gentisate
-
-
?
5-fluorosalicylate + O2
?
-
-
-
-
?
5-methylsalicylate + O2

?
-
-
-
-
?
5-methylsalicylate + O2
?
-
kcat/KM is 1.5% of the kcat/Km for gentisate
-
-
?
gentisate + O2

?
-
-
-
-
?
gentisate + O2
?
-
-
-
-
?
gentisate + O2
?
-
-
-
-
?
gentisate + O2
?
-
-
-
-
?
gentisate + O2

maleylpyruvate
-
-
-
-
?
gentisate + O2
maleylpyruvate
-
preferred substrate
-
-
?
gentisate + O2
maleylpyruvate
-
gentisate 1,2-dioxygenase with an extraordinary substrate range. Relative activities with salicylate, 5-aminosalicylate, 1-hydroxy-2-naphthoate, and gentisate with both preparations are about 1:10:40:120
-
-
?
gentisate + O2
maleylpyruvate
-
-
-
-
?
gentisate + O2
maleylpyruvate
-
gentisate 1,2-dioxygenase with an extraordinary substrate range. Relative activities with salicylate, 5-aminosalicylate, 1-hydroxy-2-naphthoate, and gentisate with both preparations are about 1:10:40:120
-
-
?
gentisate + O2
maleylpyruvate
-
preferred substrate
-
-
?
gentisate + O2
maleylpyruvate
-
-
-
-
?
gentisate + O2
maleylpyruvate
-
-
-
-
?
gentisate + O2
maleylpyruvate
-
-
-
-
?
gentisate + O2
maleylpyruvate
-
-
-
-
?
lactate + O2

?
-
-
-
-
?
salicylate + O2

2-oxohepta-3,5-dienedioic acid
-
-
-
-
?
salicylate + O2
2-oxohepta-3,5-dienedioic acid
-
a gentisate 1,2-dioxygenase with an extremely relaxed substrate specificity is responsible for the unusual oxidation of salicylate by Pseudoaminobacter salicylatoxidans BN12. Relative activities with salicylate, 5-aminosalicylate, 1-hydroxy-2-naphthoate, and gentisate with both preparations are about 1:10:40:120
-
-
?
salicylate + O2
2-oxohepta-3,5-dienedioic acid
-
kcat/KM is 6.6% of the kcat/Km for gentisate
-
-
?
salicylate + O2
2-oxohepta-3,5-dienedioic acid
-
a gentisate 1,2-dioxygenase with an extremely relaxed substrate specificity is responsible for the unusual oxidation of salicylate by Pseudoaminobacter salicylatoxidans BN12. Relative activities with salicylate, 5-aminosalicylate, 1-hydroxy-2-naphthoate, and gentisate with both preparations are about 1:10:40:120
-
-
?
salicylate + O2
2-oxohepta-3,5-dienedioic acid
-
-
-
-
?
additional information

?
-
no activity with salicylate, 3-methylsalicylate, 4-methylsalicylate, 5-methylsalicylate, 3-bromosalicylate, 4-bromosalicylate, 5-iodosalicylate, and 1-hydroxy-2-naphthoate
-
-
?
additional information
?
-
-
no activity with salicylate, 3-methylsalicylate, 4-methylsalicylate, 5-methylsalicylate, 3-bromosalicylate, 4-bromosalicylate, 5-iodosalicylate, and 1-hydroxy-2-naphthoate
-
-
?
additional information
?
-
no activity with salicylate, 3-methylsalicylate, 4-methylsalicylate, 5-methylsalicylate, 3-bromosalicylate, 4-bromosalicylate, 5-iodosalicylate, and 1-hydroxy-2-naphthoate
-
-
?
additional information
?
-
-
broad substrate specificity
-
-
?
additional information
?
-
methyl 2,5-dihydroxybenzoate, 1,4-benzoquinone, 2,5-dihydroxybenzaldehyde, 4,5-dihydroxy-1,3-benzene-disulphonic acid and 2,3,5,6-tetrachloro-1,4-benzenediol give no substrate activity
-
-
?
additional information
?
-
-
methyl 2,5-dihydroxybenzoate, 1,4-benzoquinone, 2,5-dihydroxybenzaldehyde, 4,5-dihydroxy-1,3-benzene-disulphonic acid and 2,3,5,6-tetrachloro-1,4-benzenediol give no substrate activity
-
-
?
additional information
?
-
-
benzoate does not serve as substrate
-
-
?
additional information
?
-
-
benzoate does not serve as substrate
-
-
?
additional information
?
-
-
broad substrate specificity
-
-
?
additional information
?
-
-
no activity with: 6-methylgentisate, 3,4-dimethylgentisate
-
-
?
additional information
?
-
-
the salicylate 1,2-dioxygenase from Pseudaminobacter salicylatoxidans strain BN12 is a versatile gentisate 1,2-dioxygenase that converts both gentisate (2,5-dihydroxybenzoate) and various monohydroxylated substrates
-
-
?
additional information
?
-
the purified enzyme is able to convert various salicylates that carried methyl-, fluoro-, chloro-, bromo-, or iodo-substituents in the 3-, 4-, or 5-position, although in general with much lower specific activities than observed with 5-amino- or 5-hydroxysalicylate. No activity with 6-hydroxysalicylate, 5-carboxysalicylate, 5-sulfosalicylate, 5-nitrosalicylate, 3,5-dibromosalicylate, 3,5-diiodosalicylate, or 3,4-dihydroxysalicylate
-
-
?
additional information
?
-
-
the purified enzyme is able to convert various salicylates that carried methyl-, fluoro-, chloro-, bromo-, or iodo-substituents in the 3-, 4-, or 5-position, although in general with much lower specific activities than observed with 5-amino- or 5-hydroxysalicylate. No activity with 6-hydroxysalicylate, 5-carboxysalicylate, 5-sulfosalicylate, 5-nitrosalicylate, 3,5-dibromosalicylate, 3,5-diiodosalicylate, or 3,4-dihydroxysalicylate
-
-
?
additional information
?
-
-
the salicylate 1,2-dioxygenase from Pseudaminobacter salicylatoxidans strain BN12 is a versatile gentisate 1,2-dioxygenase that converts both gentisate (2,5-dihydroxybenzoate) and various monohydroxylated substrates
-
-
?
additional information
?
-
the purified enzyme is able to convert various salicylates that carried methyl-, fluoro-, chloro-, bromo-, or iodo-substituents in the 3-, 4-, or 5-position, although in general with much lower specific activities than observed with 5-amino- or 5-hydroxysalicylate. No activity with 6-hydroxysalicylate, 5-carboxysalicylate, 5-sulfosalicylate, 5-nitrosalicylate, 3,5-dibromosalicylate, 3,5-diiodosalicylate, or 3,4-dihydroxysalicylate
-
-
?
additional information
?
-
-
GDO-II is strictly inducible by aromatic substrates such as 3-hydroxybenzoate and gentisate
-
-
?
additional information
?
-
-
GDO-II is unable to utilize gentisate that is substituted at the carbon-4 position (i.e., 4-chloro- and 4-methylgentisate)
-
-
?
additional information
?
-
-
GDO-II is strictly inducible by aromatic substrates such as 3-hydroxybenzoate and gentisate
-
-
?
additional information
?
-
-
GDO-II is unable to utilize gentisate that is substituted at the carbon-4 position (i.e., 4-chloro- and 4-methylgentisate)
-
-
?
additional information
?
-
no activity against catechol, benzoate, 5-methylsalicylate, 5-chlorosalicylate, and homogentisate
-
-
?
additional information
?
-
no activity against catechol, benzoate, 5-methylsalicylate, 5-chlorosalicylate, and homogentisate
-
-
?
additional information
?
-
-
no activity against catechol, benzoate, 5-methylsalicylate, 5-chlorosalicylate, and homogentisate
-
-
?
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A112D
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
A112G
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
A112I
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
A112S
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
A112D
-
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
-
A112G
-
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
-
A112I
-
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
-
A112S
-
the mutant gains the ability to oxidize salicylate and several other monohydroxylated substrates
-
H108D
-
complete loss of activity
H110D
-
complete loss of activity
H118D
-
complete loss of activity
H120D
-
complete loss of activity
H149D
-
complete loss of activity
H151D
-
complete loss of activity
H159D
-
complete loss of activity
H161D
-
complete loss of activity
H108D
-
complete loss of activity
-
H110D
-
complete loss of activity
-
H149D
-
complete loss of activity
-
H151D
-
complete loss of activity
-
H161D
-
complete loss of activity
-
F159Y
-
site-directed mutagenesis
G106A
-
site-directed mutagenesis, in contrast to the wild-type enzyme, mutant G106A oxidizes only gentisate, while 1-hydroxy-2-naphthoate and salicylate are not converted. The mutant shows slightly decreased activity with salicylate, but shows a higher affinity to this substratecompared to the wild-type. Salicylate is coordinated in the G106A variant with the catalytically active Fe(II) ion in an unusual and unproductive manner because of the inability of salicylate to displace a hydrogen bond that is formed between Trp104 and Asp174 in the G106A variant
G111A
-
site-directed mutagenesis
M103L
-
site-directed mutagenesis
R113G
-
site-directed mutagenesis
S147R
-
site-directed mutagenesis
G106A
-
site-directed mutagenesis, in contrast to the wild-type enzyme, mutant G106A oxidizes only gentisate, while 1-hydroxy-2-naphthoate and salicylate are not converted. The mutant shows slightly decreased activity with salicylate, but shows a higher affinity to this substratecompared to the wild-type. Salicylate is coordinated in the G106A variant with the catalytically active Fe(II) ion in an unusual and unproductive manner because of the inability of salicylate to displace a hydrogen bond that is formed between Trp104 and Asp174 in the G106A variant
-
G111A
-
site-directed mutagenesis
-
M103L
-
site-directed mutagenesis
-
R113G
-
site-directed mutagenesis
-
S147R
-
site-directed mutagenesis
-
D120K
-
complete loss of activity
E223A
-
102% relative activity compared to the wild type enzyme
G123N
-
75% relative activity compared to the wild type enzyme
G164T
-
complete loss of activity
H108D
-
no enzymatic activity
H110D
-
no enzymatic activity
H149D
-
no enzymatic activity
H151D
-
no enzymatic activity
K338Y
-
156% relative activity compared to the wild type enzyme
M146T
-
complete loss of activity
M169T
-
complete loss of activity
N153H
-
183% relative activity compared to the wild type enzyme
N43T
-
317% relative activity compared to the wild type enzyme
S113P
-
complete loss of activity
T260C
-
complete loss of activity
V326Q
-
complete loss of activity
V36A
-
complete loss of activity
Y17C
-
161% relative activity compared to the wild type enzyme
Y181D
-
68% relative activity compared to the wild type enzyme
Y181F
-
mutant demonstrates 4-, 3-, 6-, and 16fold increase in relative activity towards 2,5-dihydroxybenzoate, 3-fluoro-, 4-methyl-, and 3-methylgentisate, respectively, and shows 464% relative activity compared to the wild type enzyme for 2,5-dihydroxybenzoate
Y181H
-
98% relative activity compared to the wild type enzyme
Y284I
-
260% relative activity compared to the wild type enzyme
D120K
-
complete loss of activity
-
G123N
-
75% relative activity compared to the wild type enzyme
-
N43T
-
317% relative activity compared to the wild type enzyme
-
Y17C
-
161% relative activity compared to the wild type enzyme
-
Y181F
-
mutant demonstrates 4-, 3-, 6-, and 16fold increase in relative activity towards 2,5-dihydroxybenzoate, 3-fluoro-, 4-methyl-, and 3-methylgentisate, respectively, and shows 464% relative activity compared to the wild type enzyme for 2,5-dihydroxybenzoate
-
H108D
-
complete loss of activity
H110D
-
complete loss of activity
H118D
-
complete loss of activity
H120D
-
complete loss of activity
H149D
-
complete loss of activity
H151D
-
complete loss of activity
H159D
-
complete loss of activity
H161D
-
complete loss of activity
H108D
-
complete loss of activity
-
H110D
-
complete loss of activity
-
H149D
-
complete loss of activity
-
H151D
-
complete loss of activity
-
H161D
-
complete loss of activity
-
D175N
inactive mutant enzyme
D225N
activity is comparable to wild-type activity
E47Q
activity is comparable to wild-type activity
H119A/H121A
despite its wild-type like structural propertie, the mutant shows extremely low gentisate 1,2-dioxygenase activity
H290A/H292A
mutant can not be expressed in a soluble form
L39T
activity is comparable to wild-type activity
P253_Y254del
mutation reduces the activity to 30%
Q108E
inactive mutant enzyme
Q108E/D175N
activity is near zero
additional information

-
construction of individual knockout mutants of all three nagI genes via 2 bp unmarked gene deletion mutagenesis, all three nagI knockout mutants still contain stop codons within their nagI genes. Mutant CJ2DELTAnagI3 shows severely diminished GDO activity and grows slowest on aromatic substrates
additional information
-
double mutant Phe3Leu, Val334Ala, doubled enzymatic activity, mutants in conserved core regions with less activity
additional information
-
knockout mutant G56
additional information
-
knockout mutant G56
-
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