Native chemical ligation (NCL) is a method for coupling peptide chains. It requires that

Chapter 25, Problem 25.38

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Native chemical ligation (NCL) is a method for coupling peptide chains. It requires that one of the peptides has an N-terminal cysteine, and the C terminus of the other peptide be a thioester. The thiol of the N-terminal cysteine of peptide 2 reacts with the thioester of peptide 1 to give an initial product that contains a nonnative thioester linkage. The initial product rearranges to a more stable, amide-linked (native) peptide. Write mechanisms for the coupling and rearrangement steps in NCL.

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