Talk:Solid phase peptide synthesis

Anionic nitrogen
ist there really an anionic nitrogen? wouldn't a carbamate ion be formed in between that splits up after taking in a proton to the N?

I'd rather say it's slow because proton has to be removed from a carbon. May it should be mentioned that there is an aromatic intermediate ion.

FelixP 11:13, 5 July 2006 (UTC)

There's nothing in principle wrong with a nitrogen anion. And there's no guarantee that the nitrogen of the carbamate anion is basic enough to abstract the hydrogen from the BH+ formed in the first step.

I also disagree with (as I read it) abstractions of hydrogen from carbon being slow by their nature (and therefore this deprotection being slow). Hydrogen abstraction from a fluorene carbon is generally seen as a fast reaction, precisely because an aromatic ion is formed. Fmoc deprotection usually only takes 10–20 minutes...that's certainly not slow for an organic reaction. DMacks 04:21, 6 July 2006 (UTC)