I am pondering on the idea if it is possible to couple an "N-terminal with Fmoc-protection (but unprotected side chain) & with PTM-modification (e.g. brominated & gamma carboxylated)" amino acid, as the last residue in my peptide. I am considering this because these kinds of amino acids are less costly than amino acids with protected side chains.
Is it also possible to couple instead a free amino acid for economic purposes, since it is my last residue in my peptide?
Logically, I am thinking it is possible but could you share the risks and benefits of this strategy?
Seventeen proteinogenic amino acids are usually labelled (derivatized) with a suitable UV/fluorotag – o-phthaldehyde (OPA) for all primary amino acids and Fluorenylmethyloxycarbonyl (FMOC) for the secondary amino acid of proline. The derivatization will shift the pKa of the carboxylic acid that is used in coupling and also gives some steric hinderance for the reaction. You should be more worried about the brominated and gamma-carboxylated influence (specificity) on your reaction.
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