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Topic: Deprotection Mechanism  (Read 1633 times)

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Offline vikram

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Deprotection Mechanism
« on: August 01, 2018, 03:00:27 AM »
Dear all,

Do anyone know the possible mechanism of deprotection of 3-Bum group in Fmoc-His(3-Bum)-OH by TFA?

I think there is a formation of t-bu carbocation.However the reference provided below says there's also formation of formaldehyde type by-product. Can anyone show how it might be possible?

Mergler M, Dick F, Sax B, Schwindling J, Vorherr TH. Synthesis and Application of Fmoc‐His (3‐Bum)‐OH. Journal of peptide science: an official publication of the European Peptide Society. 2001 Sep;7(9):502-10.

Thanks in advance :)
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Offline clarkstill

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Re: Deprotection Mechanism
« Reply #1 on: August 01, 2018, 08:51:43 AM »
How are you forming the t-Bu carbocation?

I would suggest starting by protonating the most basic part of the 3-Bum group (the imidazole) and going from there...
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