Facile peptide thioester synthesis via solution-phase tosylamide preparation |
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| Authors: | Shino Manabe Tomoyuki Sugioka |
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| Affiliation: | a RIKEN (The Institute of Physical and Chemical Research), Hirosawa, Wako, Saitama 351-0198, Japan
b PRESTO, Japan Science and Technology Agency (JST), Kawaguchi, Saitama 332-1102, Japan |
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| Abstract: | Preparation of peptide thioester is essential for native chemical ligation and block condensation. Our novel methodology involves conversion of the carboxylic acid of a peptide into a thioester using p-toluenesulfonyl isocyanate, followed by alkylation, then thiol substitution. Our methodology can also be used for the preparation of glycopeptide thioesters. Furthermore, it is possible to carry out the reaction as a sequential peptide chemical ligation. |
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| Keywords: | Thioester Glycopeptide Sequential peptide ligation |
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