title: Synthesis of O-acyl isopeptides.
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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1, Hongo, Tokyo 113-0033, Japan. ysohma@mol.f.u-tokyo.ac.jp
authors.forename: Youhei
authors.initials: Y
authors.lastname: Sohma
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Kiso
mesh_terms: D000215:Acylation; D000595:Amino Acid Sequence; D016229:Amyloid beta-Peptides / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D016229:Amyloid beta-Peptides; D010455:Peptides