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Entry M0103    1.1.3.38    vanillyl-alcohol oxidase

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Step 06

Asp170 deprotonates water, which initiates a nucleophilic attack on the methoxy group, in a substitution reaction which eliminates methoxide.

GIF of Reaction Step M0103.stg06


Comment: Upon flavin reoxidation, Arg504 is deprived of its anionic partner, triggering the development of a negative charge on the quinone oxygen atom. Thus increasing the electrophilicity of the methide carbon [2].



Mechanisms

Proton Transfer
Bimolecular Nucleophilic Substitution

Mechanism Components

Overall Reactant Used
Bond Formation
Bond Cleavage
Intermediate Collapse
Intermediate Formation
Hydrolysis

Amino acids involved in the reaction step.

Amino Acid Location of Function Activity Function
Arg504 Side Chain spectator Hydrogen Bond Donor
Activator
Tyr503 Side Chain spectator Hydrogen Bond Donor
Tyr108 Side Chain spectator Hydrogen Bond Donor
Asp170 Side Chain reactant Hydrogen Bond Acceptor
Proton Acceptor
His422 Side Chain spectator Covalently Attached

Organic Cofactors involved in the reaction step

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

Reactive Centre

Bonds Formed Bonds Cleaved Bonds Changed in Order Atom Types Involved
C-O
O-H
C-O
O-H
None
C
H
O

View similar reactions in MACiE.


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