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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Native chemical ligation through in situ O to S acyl shift
Paolo Botti1, Matteo Villain, Sonia Manganiello
1Geneprot Inc., Geneva Branch, 2, Pre-de-la Fontaine, 1217 Meyrin, Switzerland. paolo.botti@geneprot.com
Abstract:
[reaction: see text] A novel strategy to generate thioester peptides compatible with Fmoc chemistry is presented. Peptide-C(alpha)oxy-(2-mercapto-1-carboxyamide)ethyl ester undergoes an O to S acyl shift during ligation and the newly formed thioester intermediate reacts with an N-terminal cysteine fragment generating a product with native amide bond at the ligation site.
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