O-Acyl isopeptide method: development of an O-acyl isodipeptide unit for Boc SPPS and its application to the synthesis of Aβ1-42 isopeptide

• Published in: Journal of peptide science 2014-09, Vol.20 (9), p.669-674
• Main Authors: Yoshiya, Taku, Uemura, Tsuyoshi, Maruno, Takahiro, Kubo, Shigeru, Kiso, Yoshiaki, Sohma, Youhei, Kobayashi, Yuji, Yoshizawa-Kumagaye, Kumiko, Nishiuchi, Yuji
• Format: Article
• Language: English
• Subjects: Alzheimer's disease; Amyloid beta-Peptides - chemical synthesis; Amyloid beta-Peptides - chemistry; Amyloid beta-Peptides - isolation & purification; amyloid β peptide; difficult sequence-containing peptide; Humans; Islet Amyloid Polypeptide - chemical synthesis; Islet Amyloid Polypeptide - chemistry; Islet Amyloid Polypeptide - isolation & purification; O-acyl isopeptide; O-to-N intramolecular acyl migration; Peptide Fragments - chemical synthesis; Peptide Fragments - chemistry; Peptide Fragments - isolation & purification; Protein Structure, Secondary; Solid-Phase Synthesis Techniques - methods; SPPS
• ISSN: 1075-2617; 1099-1387
• DOI: 10.1002/psc.2662

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. The O‐acyl isopeptide method was developed for the efficient preparation of difficult sequence‐containing peptides. 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.