Side reactions in peptide synthesis. V.A reexamination of the mixed anhydride method.
Acylation of amino acid beta-naphthylamides with protected (Boc) amino acidisobutylcarbonic acid mixed anhydrides resulted in each case in the formation of some undesired by-product: an isobutyloxycarbonylamino acid beta-naphthylamide. The amount of this second acylation product was particularly high, with the hindered amino acids valine and isoleucine as carboxyl-components. The nature of the amino component had no major influence on the extent of this side reaction.
D000215:Acylation; D000595:Amino Acid Sequence; D000812:Anhydrides; D055598:Chemical Phenomena; D002621:Chemistry; D010455:Peptides / Q000138:chemical synthesis*
D000812:Anhydrides; D010455:Peptides