Native Chemical Ligation through in Situ O to S Acyl Shift
Organic Letters2004Vol. 6(26), pp. 4861–4864
Citations Over TimeTop 14% of 2004 papers
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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