I was wondering if in solid phase peptide synthesis (SPPS) the unprotected hydroxyl groups are prone to undergo side reactions during the coupling and deprotection steps, e.g ester formation with the newly added amino acid. Or do you use always the fully side chain protected amino acids?
Yes it is mandatary to protect hydroxyl side chains in aminoacids because the impurities will form which may lead to decreasing in the Purity.
Yes.. it is always a necessity to use fully protected amino acids during SPPS. the amino group is either protected with Boc or Fmoc and side chain via various sise chain protecting groups, which is usually Trityl in case of -OH groups. and they can be easily bought. you will end up getting a number of side reactions if you don't do that.
The longer the synthesis the greater the possibility of various side reactions and other problems typical to SPPS. Fully protected AA's reduce those risks. In my case the OH group is usually protected by tBu.
I think that it is necessary, because OH is compararively reactive and you will have a lot of side products.
Yes it is mandatory, since they might compete as nucleophiles upon any coupling.
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