A reversible protection strategy to improve Fmoc-SPPS of peptide thioesters by the N-Acylurea approach.

@article{Mahto2011ARP,
  title={A reversible protection strategy to improve Fmoc-SPPS of peptide thioesters by the N-Acylurea approach.},
  author={Santosh K. Mahto and Cecil J Howard and John C. Shimko and Jennifer J. Ottesen},
  journal={Chembiochem : a European journal of chemical biology},
  year={2011},
  volume={12 16},
  pages={2488-94}
}
C-terminal peptide thioesters are an essential component of the native chemical ligation approach for the preparation of fully or semisynthetic proteins. However, the efficient generation of C-terminal thioesters by Fmoc solid-phase peptide synthesis remains a challenge. The recent N-acylurea approach to thioester synthesis relies on the deactivation of one amine of 3,4-diaminobenzoic acid (Dbz) during Fmoc SPPS. Here, we demonstrate that this approach results in the formation of side products… CONTINUE READING
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