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Problem of aspartimide formation in Fmoc-based solid-phase peptide synthesis using Dmab group to protect side chain of aspartic acid

✍ Scribed by JarosŁaw Ruczyński; Brygida Lewandowska; Piotr Mucha; Piotr Rekowski

Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
132 KB
Volume
14
Category
Article
ISSN
1075-2617

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✦ Synopsis

Abstract

The sequence‐dependent, acid‐ or base‐catalysed aspartimide formation is one of the most serious side reactions in solid‐phase synthesis of peptides containing aspartic acid. In the present work, we investigated the susceptibility of 4‐{N‐[1‐(4,4‐dimethyl‐2,6‐dioxocyclohexylidene)‐3‐methylbutyl]amino}benzyl (Dmab), an aspartic acid β‐carboxy side‐chain protecting group, for aspartimide formation. As a model, 15‐amino acid‐residue galanin fragment analogue containing the Asp‐Ala motif was used during Fmoc‐based solid‐phase synthesis. Our study showed a strong tendency of Dmab‐protected peptide to form aspartimide with unusual high efficiency. Furthermore, to investigate the susceptibility of Asp‐Ala motif for aspartimide formation during the synthesis using Asp(ODmab), a 5‐amino acid‐residue galanin fragment LGPDA, different types of resin linkers, variety of Fmoc‐deprotection conditions and coupling methods were applied. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.

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