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Literature summary extracted from
- Structural and functional characterization of 4-hydroxyphenylacetate 3-hydroxylase from Escherichia coli (2020), ChemBioChem, 21, 163-170 .
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 1.14.14.9 | synthesis | enzyme shows relatively broad substrate specificity, which allows the conversion of a number of non-natural phenolic compounds, into the corresponding catechols. The reaction can be performed based on formate as the electron donor and the organometallic complex [Rh(bpy)-Cp*(H2O)]2+ (Cp*: 1,2,3,4,5-pentamethylcyclopentadiene, bpy: 2,2'-bipyridyl) as the catalyst for FAD reduction | Escherichia coli |
Crystallization (Commentary)
| EC Number | Crystallization (Comment) | Organism |
|---|---|---|
| 1.14.14.9 | in complex with FAD, to 1.94 A resolution | Escherichia coli |
Protein Variants
| EC Number | Protein Variants | Comment | Organism |
|---|---|---|---|
| 1.14.14.9 | H155A | drastically decreased hydroxylase activity with substrate 3-hydroxyphenylacetate | Escherichia coli |
| 1.14.14.9 | I157A | complete loss of hydroxylase activity | Escherichia coli |
| 1.14.14.9 | I157G | complete loss of hydroxylase activity | Escherichia coli |
| 1.14.14.9 | I157S | complete loss of hydroxylase activity | Escherichia coli |
| 1.14.14.9 | R113A | drastically decreased hydroxylase activity with substrate 3-hydroxyphenylacetate | Escherichia coli |
| 1.14.14.9 | S210A | drastically decreased hydroxylase activity | Escherichia coli |
| 1.14.14.9 | S210Q | drastically decreased hydroxylase activity | Escherichia coli |
| 1.14.14.9 | V158G | complete loss of hydroxylase activity | Escherichia coli |
| 1.14.14.9 | Y117A | drastically decreased hydroxylase activity with substrate 3-hydroxyphenylacetate | Escherichia coli |
KM Value [mM]
| EC Number | KM Value [mM] | KM Value Maximum [mM] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.9 | 0.0094 | - |
3-hydroxyphenylacetate | pH 7.5, 23°C | Escherichia coli |  |
| 1.14.14.9 | 0.0247 | - |
DL-4-hydroxymandelic acid | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.0339 | - |
2-(4-hydroxyphenyl)ethanol | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.0461 | - |
(3,4-dihydroxyphenyl)acetate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.054 | - |
4-coumarate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.253 | - |
phenol | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.515 | - |
methyl 4-hydroxybenzoate | pH 7.5, 23°C | Escherichia coli | |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 1.14.14.9 | Escherichia coli | - |
- |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 1.14.14.9 | (3,4-dihydroxyphenyl)acetate + NADH + H+ + O2 | - |
Escherichia coli | ? + NAD+ + H2O | - |
? | |
| 1.14.14.9 | 2-(4-hydroxyphenyl)ethanol + NADH + H+ + O2 | - |
Escherichia coli | ? + NAD+ + H2O | - |
? | |
| 1.14.14.9 | 3-hydroxyphenylacetate + NADH + H+ + O2 | - |
Escherichia coli | 3,4-hydroxyphenylacetate + NAD+ + H2O | - |
? | |
| 1.14.14.9 | 4-coumarate + NADH + H+ + O2 | - |
Escherichia coli | ? + NAD+ + H2O | - |
? | |
| 1.14.14.9 | DL-4-hydroxymandelic acid + NADH + H+ + O2 | - |
Escherichia coli | ? + NAD+ + H2O | - |
? | |
| 1.14.14.9 | methyl 4-hydroxybenzoate + NADH + H+ + O2 | - |
Escherichia coli | ? + NAD+ + H2O | - |
? | |
| 1.14.14.9 | additional information | no substrates: benzoic acid, dihydroxybenzoic acid, 4-methoxyphenylacetic acid, catechol, 4-hydroxy-D-2-phenylglycine, 4-hydroxy-L-2-phenylglycine, 3-hydroxy-4-methoxyphenylacetic acid, 4-tert-butylphenol, 3-methoxyphenylacetic acid, 4-hydroxy-3-methoxyphenylacetic acid | Escherichia coli | ? | - |
- |
|
| 1.14.14.9 | phenol + NADH + H+ + O2 | - |
Escherichia coli | ? + NAD+ + H2O | - |
? | |
Turnover Number [1/s]
| EC Number | Turnover Number Minimum [1/s] | Turnover Number Maximum [1/s] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.9 | 0.2 | - |
methyl 4-hydroxybenzoate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.3 | - |
phenol | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 0.6 | - |
4-coumarate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 1.5 | - |
2-(4-hydroxyphenyl)ethanol | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 2.1 | - |
(3,4-dihydroxyphenyl)acetate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 2.7 | - |
DL-4-hydroxymandelic acid | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 4.4 | - |
3-hydroxyphenylacetate | pH 7.5, 23°C | Escherichia coli | |
kcat/KM [mM/s]
| EC Number | kcat/KM Value [1/mMs-1] | kcat/KM Value Maximum [1/mMs-1] | Substrate | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 1.14.14.9 | 0.39 | - |
methyl 4-hydroxybenzoate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 1.1 | - |
phenol | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 11 | - |
4-coumarate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 44 | - |
2-(4-hydroxyphenyl)ethanol | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 46 | - |
(3,4-dihydroxyphenyl)acetate | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 110 | - |
DL-4-hydroxymandelic acid | pH 7.5, 23°C | Escherichia coli | |
| 1.14.14.9 | 470 | - |
3-hydroxyphenylacetate | pH 7.5, 23°C | Escherichia coli | |
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