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Information on EC 1.17.9.1 - 4-methylphenol dehydrogenase (hydroxylating)

for references in articles please use BRENDA:EC1.17.9.1

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IUBMB Comments

This bacterial enzyme contains a flavin (FAD) subunit and a cytochrome c subunit. The flavin subunit abstracts two hydrogen atoms from the substrate, forming a quinone methide intermediate, then hydrates the latter at the benzylic carbon with a hydroxyl group derived from water. The protons are lost to the bulk solvent, while the electrons are passed to the heme on the cytochrome subunit, and from there to azurin, a small copper-binding protein that is co-localized with the enzyme in the periplasm. The first hydroxylation forms 4-hydroxybenzyl alcohol; a second hydroxylation converts this into 4-hydroxybenzaldehyde.

The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
hide(Overall reactions are displayed. Show all >>)
4-methylphenol
+
4
oxidized azurin
+
H2O
=
4-hydroxybenzaldehyde
+
4
reduced azurin
+
4
H+
+
4
oxidized azurin
+
=
+
4
+
4

Synonyms
p-cresol methylhydroxylase, p-cresol methylhydroxylase a, para-cresol methylhydroxylase, more

REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
4-hydroxybenzyl alcohol + 2 oxidized azurin = 4-hydroxybenzaldehyde + 2 reduced azurin + 2 H+
show the reaction diagram
(1b)
-
-
-
4-methylphenol + 2 oxidized azurin + H2O = 4-hydroxybenzyl alcohol + 2 reduced azurin + 2 H+
show the reaction diagram
(1a)
-
-
-
4-methylphenol + 4 oxidized azurin + H2O = 4-hydroxybenzaldehyde + 4 reduced azurin + 4 H+
show the reaction diagram
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