docberto - 30-5-2005 at 16:54
Would it be possible to do acylation with an amino acid that isn't N-protected? I know an acyl halide or acyl anhydride would readily react with
any available nitrogen. But would the N-protection be necessary when using the acid itself and using polyphosphoric acid or P2O5 as the Lewis acid?
stoichiometric_steve - 22-12-2007 at 06:17
i think that lewis acids might most likely catalyze the formation of peptides as well.
Aluminium Tungstophosphate may do the job, or may not. experiment is king.
solo - 27-12-2007 at 14:24
Just look at the Dakin-West Reaction and you will see that that both the COOH and the NH2 will get acylated unless you protect the amine group aside
you need a strong base to do the deed.....see March 5th edition page 812 under "Replacement of a Carboxyl Group by an Acyl Group".........solo
[Edited on 27-12-2007 by solo]