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Entry M0103    1.1.3.38    vanillyl-alcohol oxidase

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Step 02

The oxyanion collapses with double bond rearrangement, eliminating a hydride from the 1-methoxy carbon, which is added to FAD.

Rate Determining Step

This reaction is irreversible.

GIF of Reaction Step M0103.stg02



Mechanisms

Aromatic Unimolecular Elimination by the conjugate base
Hydride Transfer
Aromatic Bimolecular Nucleophilic Addition

Mechanism Components

Cofactor Used
Bond Formation
Bond Cleavage
Bond Order Change
Intermediate Formation

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Arg504 Side Chain spectator Hydrogen Bond Donor
Electrostatic Stabiliser
Tyr503 Side Chain spectator Hydrogen Bond Donor
Electrostatic Stabiliser
Tyr108 Side Chain spectator Hydrogen Bond Donor
Electrostatic Stabiliser
Asp170 Side Chain spectator Not Active
His422 Side Chain spectator Covalently Attached
Activator

Organic Cofactors involved in the reaction step

Cofactor Type Cofactor Activity Function
FAD FAD600 reactant Covalently Attached
Hydrogen Bond Acceptor
Hydrogen Bond Donor
Hydride Acceptor

Reactive Centre

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

View similar reactions in MACiE.


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