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revised on 22.08.2020 and posted on 24.08.2020by Skander Abboud, Vincent AUCAGNE
An in-depth study of the Fmoc-based solid phase peptide synthesis of
N-Hnb-Cys crypto-thioester peptides, advantageous building blocks for
the native chemical ligation-based synthesis of proteins, led to the
identification of epimerized and imidazolidinone side products formed
during a key reductive amination step. The understanding of the
underlying reaction mechanisms was crucial for the developement of an
automatable optimized synthetic protocol.