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Bis(2-sulfanylethyl)amido peptides enable native chemical ligation at proline and minimize deletion side-product
Laurent Raibaut1, Phillip Seeberger, Oleg Melnyk
1UMR CNRS 8161, Pasteur Institute of Lille , 59021 Lille, France.
Organic Letters
|October 15, 2013
Abstract:
Native chemical ligation of C-terminal peptidyl prolyl alkylthioesters with N-terminal cysteinyl peptides usually exhibits poor kinetic rates compared to other C-terminal amino acid residues. It is shown here that the reaction is accompanied by the formation of a deletion side product which is minimized by using a bis(2-sulfanylethyl)amido (SEA) thioester surrogate at a mildly acidic pH.

