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

J Pept Sci. 2014 Sep;20(9):669-74. doi: 10.1002/psc.2662. Epub 2014 May 28.

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.

Keywords: Alzheimer's disease; O-acyl isopeptide; O-to-N intramolecular acyl migration; SPPS; amyloid β peptide; difficult sequence-containing peptide.

MeSH terms

  • Amyloid beta-Peptides / chemical synthesis*
  • Amyloid beta-Peptides / chemistry
  • Amyloid beta-Peptides / isolation & purification*
  • Humans
  • Islet Amyloid Polypeptide / chemical synthesis
  • Islet Amyloid Polypeptide / chemistry
  • Islet Amyloid Polypeptide / isolation & purification
  • Peptide Fragments / chemical synthesis*
  • Peptide Fragments / chemistry
  • Peptide Fragments / isolation & purification*
  • Protein Structure, Secondary
  • Solid-Phase Synthesis Techniques / methods*

Substances

  • Amyloid beta-Peptides
  • Islet Amyloid Polypeptide
  • Peptide Fragments
  • amyloid beta-protein (1-42)