Mechanism: acid-catalyzed rearrangement (hydride/methyl shifts)

this is done by an enzyme but I'm supposed to propose the rearrangement that occurs. is this plausible?

Question

Mechanism: acid-catalyzed rearrangement (hydride/methyl shifts)

this is done by an enzyme but I'm supposed to propose the rearrangement that occurs. is this plausible?

aaronq · Answer

attachment

abb0t · Answer

Yes, the mechanism you proposed there looks correct. The charge sort of "opens" the ring causing a 1, 2-methyl shift. Idk what the BH is though. Is that just some acid?

aaronq · Answer

hm we'll it's supposed to be a general base. It's not stated it in the question but it says that it's acid catalyzed so i'm guessing a proton is supposed to come off somehow, so i just included B as any amino acid residue in the active site that can act as a base.

aaronq · Answer

because i couldn't think of another way to get rid of the proton

abb0t · Answer

Oh. Well, looks plausible on paper. I don't know if it works, cause you know how there are methods that may work on paper but not in real life...

aaronq · Answer

ohh yeah of course. This is just the rearrangement, the actual work is done by an enzyme so i'm  just speculating on the steps.  thanks still !