Abstract
O-Acyl isopeptides, in which the N-acyl linkage on the hydroxyamino acid residue (e.g., Ser and Thr) is replaced with an O-acyl linkage, generally possess superior water-solubility to their corresponding native peptides, as well as other distinct physicochemical properties. In addition, O-acyl isopeptides can be rapidly converted into their corresponding native peptide under neutral aqueous conditions through an O-to-N acyl migration. By exploiting these characteristics, researchers have applied the O-acyl isopeptide method to various peptide-synthesis fields, such as the synthesis of aggregative peptides and convergent peptide synthesis. This O-acyl-isopeptide approach also serves as a means to control the biological function of the peptide in question. Herein, we report the synthesis of O-acyl isopeptides and some of their applications.
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