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‘O-Acyl isopeptide method’ for peptide synthesis: Solvent effects in the synthesis of Aβ1–42 isopeptide using ‘O-acyl isodipeptide unit’

✍ Scribed by Atsuhiko Taniguchi; Taku Yoshiya; Naoko Abe; Fukue Fukao; Youhei Sohma; Tooru Kimura; Yoshio Hayashi; Yoshiaki Kiso

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
278 KB
Volume
13
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

‘O‐Acyl isopeptide method’ is an efficient synthetic method for peptides. We designed ‘O‐acyl isodipeptide units’, Boc‐Ser/Thr(Fmoc‐Xaa)‐OH, as important building blocks to enable routine use of the O‐acyl isopeptide method. In the synthesis of an Aβ1–42 isopeptide using O‐acyl isodipeptide unit Boc–Ser(Fmoc–Gly)–OH, a side reaction, resulting in the deletion of Ser^26^ in the O‐acyl isopeptide structure, was noticed during coupling of the unit. We observed that the side reaction occurred during the activation step and was solvent‐dependent. In DMF or NMP, an intramolecular side reaction, originating from the activated species of the unit, occurred during the activation step. In non‐polar solvents such as CHCl~3~ or CH~2~Cl~2~, the side reaction was less likely to occur. Using CH~2~Cl~2~ as solvent in coupling the unit, the target Aβ1–42 isopeptide was synthesized with almost no major side reaction. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.

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