The interest in bioactive peptides as therapeutic agents has increased over the years due to their large surface area, site-selectivity and synthetic accessibility. Although chemical synthesis has enabled access to a wide range of peptides, there remain limitations that result in part from the rigid adherence to the paradigm of assembling peptides from the C to N direction on solid support. Improved accessibility to more complex peptide structures may be possible with more diverse assembly options. However, the C terminus of peptides are prone to epimerization due to the lowered pKa of the a-C–H during activation of the carboxylic acid. This challenge has prevented widespread use of N to C and bidirectional peptide assembly. The Stockdill lab has developed an approach that allows for the assembly of peptides from the N to C directions with no observable epimerization and has applied it towards the synthesis of oligopeptide sequences.

Mild activation strategy enables epimerization-free N-to-C solid phase peptide synthesis

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