Abstract
Hydroxyl and carboxyl plays critical roles in peptide synthesis. The carboxyl group is the underlying basis for peptide bond construction. It could, nonetheless, be entangled in a variety of side reactions in the process of peptide synthesis that are characteristic of carboxyl group, e.g., imide formation, transesterification, other undesired esterification, and so forth. The hydroxyl group could also induce a plethora of side reactions in peptide synthesis due to its evident nucleophilicity that mediates acyl migration, and consequent peptide fragmentation. Some of the carboxyl and hydroxyl-related side reactions, e.g., aspartimide formation, acidolysis of the peptide C-terminal N-Me-AA, O-acyl isopeptide-induced des-Ser/Thr formation, sulfonation, and acyl migration have been dedicatedly introduced in other sections, and will not be reiterated in this chapter.
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