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Side Reactions in Peptide Synthesis || Cys Disulfide-Related Side Reactions in Peptide Synthesis


Abstract The acid catalyzed O → C migration of the benzyl group in the side chain of tyrosine could be reduced by applying HBr in a mixture of phenol and p-cresol instead of HBr in trifluoroacetic acid for acidolytic deprotection. This side reaction occurs also during the removal of Boc groups. The loss of O-benzyl protection and the formation of 3-benzyltyrosine residues could be suppressed by the application of a 7:3 mixture of trifluoroacetic acid and acetic acid. The acid- and base-catalyzed ring closure of β-benzylaspartyl residues to aminosuccinyl derivatives was also studied. In this case HBr in trifluoroacetic acid was found to be relatively harmless. 

Deprotection with HBr in a mixture of trifluoroacetic acid and p-cresol can be applied for peptides that contain both β-benzylaspartyl and O-benzyltyrosyl residues. An attempt to reduce the rate of the base-catalyzed side reaction by application of hindered tertiary amines was abandoned because the tertiary amines which were effective in this respect led to significant reduction of the rate of the desired reaction, the aminolysis of active esters, as well.

Disulfide moiety is ubiquitously located in many peptides and plays important roles in the establishment and reinforcement of the peptide/protein overall structure, as well as the regulation of the activity of the peptide/protein. Due to the inherent instability of the disulfide bond toward a variety of conditions it could undergo divergent side reactions such as a thiol-disulfide exchange that reversibly modifies the pattern of the disulfide bonds and hence the activity of the affected peptide/protein molecule. On top of this process disulfide bridge moiety could also suffer from other degradation such as hydrolysis, β-elimination or relatively infrequent α-degradation, leading to the formation of degradative side products, e.g., trisulfide or lanthionine derivatives.

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