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Literature summary for 1.14.14.9 extracted from

  • Deng, Y.; Faivre, B.; Back, O.; Lombard, M.; Pecqueur, L.; Fontecave, M.
    Structural and functional characterization of 4-hydroxyphenylacetate 3-hydroxylase from Escherichia coli (2020), ChemBioChem, 21, 163-170 .
    View publication on PubMed
Search for more literature for 1.14.14.9

Application

Application Comment Organism
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)

Crystallization (Comment) Organism
in complex with FAD, to 1.94 A resolution Escherichia coli

Protein Variants

Protein Variants Comment Organism
H155A drastically decreased hydroxylase activity with substrate 3-hydroxyphenylacetate Escherichia coli
I157A complete loss of hydroxylase activity Escherichia coli
I157G complete loss of hydroxylase activity Escherichia coli
I157S complete loss of hydroxylase activity Escherichia coli
R113A drastically decreased hydroxylase activity with substrate 3-hydroxyphenylacetate Escherichia coli
S210A drastically decreased hydroxylase activity Escherichia coli
S210Q drastically decreased hydroxylase activity Escherichia coli
V158G complete loss of hydroxylase activity Escherichia coli
Y117A drastically decreased hydroxylase activity with substrate 3-hydroxyphenylacetate Escherichia coli

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
0.0094
-
 3-hydroxyphenylacetate pH 7.5, 23°C Escherichia coli
0.0247
-
 DL-4-hydroxymandelic acid pH 7.5, 23°C Escherichia coli
0.0339
-
 2-(4-hydroxyphenyl)ethanol pH 7.5, 23°C Escherichia coli
0.0461
-
 (3,4-dihydroxyphenyl)acetate pH 7.5, 23°C Escherichia coli
0.054
-
 4-coumarate pH 7.5, 23°C Escherichia coli
0.253
-
 phenol pH 7.5, 23°C Escherichia coli
0.515
-
 methyl 4-hydroxybenzoate pH 7.5, 23°C Escherichia coli

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(3,4-dihydroxyphenyl)acetate + NADH + H+ + O2
-
 Escherichia coli ? + NAD+ + H2O
-
 ?
2-(4-hydroxyphenyl)ethanol + NADH + H+ + O2
-
 Escherichia coli ? + NAD+ + H2O
-
 ?
3-hydroxyphenylacetate + NADH + H+ + O2
-
 Escherichia coli 3,4-hydroxyphenylacetate + NAD+ + H2O
-
 ?
4-coumarate + NADH + H+ + O2
-
 Escherichia coli ? + NAD+ + H2O
-
 ?
DL-4-hydroxymandelic acid + NADH + H+ + O2
-
 Escherichia coli ? + NAD+ + H2O
-
 ?
methyl 4-hydroxybenzoate + NADH + H+ + O2
-
 Escherichia coli ? + NAD+ + H2O
-
 ?
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 ?
-
-
phenol + NADH + H+ + O2
-
 Escherichia coli ? + NAD+ + H2O
-
 ?

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
0.2
-
 methyl 4-hydroxybenzoate pH 7.5, 23°C Escherichia coli
0.3
-
 phenol pH 7.5, 23°C Escherichia coli
0.6
-
 4-coumarate pH 7.5, 23°C Escherichia coli
1.5
-
 2-(4-hydroxyphenyl)ethanol pH 7.5, 23°C Escherichia coli
2.1
-
 (3,4-dihydroxyphenyl)acetate pH 7.5, 23°C Escherichia coli
2.7
-
 DL-4-hydroxymandelic acid pH 7.5, 23°C Escherichia coli
4.4
-
 3-hydroxyphenylacetate pH 7.5, 23°C Escherichia coli

kcat/KM [mM/s]

kcat/KM Value [1/mMs-1] kcat/KM Value Maximum [1/mMs-1] Substrate Comment Organism Structure
0.39
-
 methyl 4-hydroxybenzoate pH 7.5, 23°C Escherichia coli
1.1
-
 phenol pH 7.5, 23°C Escherichia coli
11
-
 4-coumarate pH 7.5, 23°C Escherichia coli
44
-
 2-(4-hydroxyphenyl)ethanol pH 7.5, 23°C Escherichia coli
46
-
 (3,4-dihydroxyphenyl)acetate pH 7.5, 23°C Escherichia coli
110
-
 DL-4-hydroxymandelic acid pH 7.5, 23°C Escherichia coli
470
-
 3-hydroxyphenylacetate pH 7.5, 23°C Escherichia coli