Entry M0130    naphthalene 1,2-dioxygenase

Previous Step     Next Step

Step 04

The peroxo group attacks the naphthalene substrate in a nucleophilic addition that causes the double bond to attack the peroxo group, cleaving the O-O bond and forming the epoxide intermediate.

Rate Determining Step

GIF of Reaction Step M0130.stg04

Comment: Bassan et al. [3] suggest that a feasible reaction pathway leading to naphtalene dioxygenation could be accessed only for the hydroperoxo-iron(III) species.


Bimolecular Nucleophilic Addition
Bimolecular Nucleophilic Substitution

Mechanism Components

Overall Reactant Used
Bond Formation
Bond Cleavage
Bond Order Change
Intermediate Formation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
His104 Side Chain spectator Metal Ligand
Hydrogen Bond Donor
Asp205E Side Chain spectator Hydrogen Bond Acceptor
His208E Side Chain spectator Metal Ligand
Hydrogen Bond Donor

Organic Cofactors involved in the reaction step

Cofactor Type Cofactor Activity Function
FAD FAD spectator Not Active

Metal Cofactors involved in Step 04

Metal Type Metal Identity Chain Activity Function
iron FES 451 A spectator Not Active
iron FE 452 A spectator Substrate Binding
iron FE(not in PDB) 1 x spectator Not Present
iron FE(not in PDB) 2 x spectator Not Present

Reactive Centre

Bonds Formed Bonds Cleaved Bonds Changed in Order Atom Types Involved
The C-C bond changes from a double to single bond

View similar reactions in MACiE.