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Dr. Ryo Okamoto, Keiko Morooka and Prof. Dr. Yasuhiro Kajihara A Synthetic Approach to a Peptide α-Thioester from an Unprotected Peptide through Cleavage and Activation of a Specific Peptide Bond by N-Acetylguanidine Angewandte Chemie International Edition 51

Version of Record online: 9 NOV 2011 | DOI: 10.1002/anie.201105601

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A different route to peptide α-thioesters through a new peptide-bond-cleavage method at a cysteine residue by S-thiocarbonylation and subsequent treatment with N-acetylguanidine is described (see scheme). The resultant peptidyl-N-acetylguanidine can be converted into the corresponding peptide α-thioester and is also usable as an alternative to a peptide α-thioester. This method allows efficient kinetically controlled ligation in the presence of thiols.

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