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What is the mechanism of benzylamine oxidation by flavins?
Accepted Answer
The oxidation of benzylamine by flavins is a complex reaction involving several steps. The mechanism can be summarized as follows:
1. Initial Binding: Benzylamine binds to the flavin cofactor, likely through an interaction with the N5 atom of the flavin ring. This interaction facilitates electron transfer from the benzylamine to the flavin.
2. Hydride Transfer: The benzylamine undergoes a hydride transfer to the flavin, resulting in the formation of a reduced flavin species (FADH2) and an iminium ion intermediate. This step is often the rate-limiting step in the reaction.
3. Proton Transfer: The iminium ion intermediate is protonated by the solvent or another molecule in the solution. This protonation step stabilizes the iminium ion.
4. Hydrolysis: The protonated iminium ion undergoes hydrolysis, resulting in the formation of benzaldehyde and ammonia. The hydrolysis step is usually fast and irreversible.
5. Flavin Regeneration: The reduced flavin (FADH2) is reoxidized by an electron acceptor, such as molecular oxygen, regenerating the oxidized flavin (FAD) and completing the catalytic cycle.
The specific details of the mechanism can vary depending on the nature of the flavin cofactor, the solvent, and the pH of the reaction environment.
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