Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters

Victor Terrier (1) , Agnès F. Delmas (1) , Vincent Aucagne (1)

1 CBM - Centre de biophysique moléculaire

We herein introduce a straightforward synthetic route to cysteine-containing cyclic peptides based on the intramolecular native chemical ligation of in situ generated thioesters. Key precursors are N-Hnb-Cys crypto-thioesters, easily synthesized by Fmoc-based SPPS. The strategy is applied to a representative range of naturally occurring cyclic disulfide-rich peptide sequences.

Domaines: Chimie

Victor Terrier, Agnès F. Delmas, Vincent Aucagne. Efficient synthesis of cysteine-rich cyclic peptides through intramolecular native chemical ligation of N-Hnb-Cys peptide crypto-thioesters. Organic & Biomolecular Chemistry, 2017, 15 (2), pp.316 - 319. ⟨10.1039/c6ob02546c⟩. ⟨hal-01618781⟩