Oxidoreductases;
Acting on CH or CH2 groups;
With a copper protein as acceptor
BRITE hierarchy

4-methylphenol:oxidized azurin oxidoreductase (methyl-hydroxylating)

4-methylphenol + 4 oxidized azurin + H2O = 4-hydroxybenzaldehyde + 4 reduced azurin + 4 H+ (overall reaction) [RN:R02675];
(1a) 4-methylphenol + 2 oxidized azurin + H2O = 4-hydroxybenzyl alcohol + 2 reduced azurin + 2 H+ [RN:R12133];
(1b) 4-hydroxybenzyl alcohol + 2 oxidized azurin = 4-hydroxybenzaldehyde + 2 reduced azurin + 2 H+ [RN:R12134]

R02675 R12133 R12134;
(other) R11194
Reaction

4-methylphenol [CPD:C01468];
oxidized azurin [CPD:C05357];
H2O [CPD:C00001];
4-hydroxybenzyl alcohol [CPD:C17467]

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.

EC 1.17.9.1 created 1983 as EC 1.17.99.1, modified 2001, modified 2011, modified 2015, transferred 2018 to EC 1.17.9.1

1  [PMID:588247]

2  [PMID:7391034]

3  [PMID:3920077]

4  [PMID:2722739]

5  [PMID:1697166]

6  [PMID:17449613]

7  [PMID:18658262]