title: O-acyl isopeptide method: development of an O-acyl isodipeptide unit for Boc SPPS and its application to the synthesis of Aβ1-42 isopeptide.
abstract: The O-acyl isopeptide method was developed for the efficient preparation of difficult sequence-containing peptide. Furthermore, development of the O-acyl isodipeptide unit for Fmoc chemistry simplified its synthetic procedure by solid-phase peptide synthesis. Here, we report a novel isodipeptide unit for Boc chemistry, and the unit was successfully applied to the synthesis of amyloid β peptide. Combination of Boc chemistry and the isodipeptide unit would be an effective method for the synthesis of many difficult peptides. Copyright © 2014 European Peptide Society and John Wiley & Sons, Ltd.
authors.affiliation: Peptide Institute, Inc., Osaka, 567-0085, Japan.
authors.forename: Taku
authors.initials: T
authors.lastname: Yoshiya
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Uemura
authors.forename: Takahiro
authors.initials: T
authors.lastname: Maruno
authors.forename: Shigeru
authors.initials: S
authors.lastname: Kubo
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Kiso
authors.forename: Youhei
authors.initials: Y
authors.lastname: Sohma
authors.forename: Yuji
authors.initials: Y
authors.lastname: Kobayashi
authors.forename: Kumiko
authors.initials: K
authors.lastname: Yoshizawa-Kumagaye
authors.forename: Yuji
authors.initials: Y
authors.lastname: Nishiuchi
mesh_terms: D016229:Amyloid beta-Peptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D006801:Humans; D058228:Islet Amyloid Polypeptide / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D017433:Protein Structure, Secondary; D060327:Solid-Phase Synthesis Techniques / Q000379:methods*
chemical_list: D016229:Amyloid beta-Peptides; D058228:Islet Amyloid Polypeptide; D010446:Peptide Fragments; C075222:amyloid beta-protein (1-42)
keywords: Alzheimer's disease; O-acyl isopeptide; O-to-N intramolecular acyl migration; SPPS; amyloid β peptide; difficult sequence-containing peptide