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. Author manuscript; available in PMC: 2021 Sep 30.
Published in final edited form as: Org Biomol Chem. 2020 Sep 30;18(37):7273–7290. doi: 10.1039/d0ob01421d

Figure 2: Native Chemical Ligation (NCL)-Assisted Trapping of Thiolactone Peptides.

Figure 2:

A) The general procedure involves treating cell supernatant with functionalized resin and NCL reagents in order to trap the peptide on the insoluble resin. B) A thiol-thioester exchange reaction traps the peptide on the resin. This reaction will be reversible if it occurs with other cysteines but is irreversible when reacting with the cysteine on the resin due to an S to N acyl shift.