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Sequence Diversification by Divergent C‑Terminal Elongation of Peptides

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journal contribution
posted on 2018-01-02, 00:00 authored by Christine A. Arbour, Ramona E. Stamatin, Jennifer L. Stockdill
Sequence diversification at the C terminus is traditionally limited by significant epimerization of the C-terminal residue during its activation toward nucleophilic attack, thus mandating repetition of the peptide synthesis for each targeted variation. Here, we accomplish divergent C-terminal elongation of a single peptide substrate with concomitant resin cleavage via displacement of an N-acyl urea moiety. Sterically hindered amino acids such as Ile and Pro are well-tolerated in this approach, which proceeds reasonable conversion and no detectable epimerization of the starting peptide’s C-terminal amino acid.