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Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

ABSTRACT: The synthesis of polypeptides on solid phase via mediation by isonitriles is described. The acyl donor is a thioacid, which presumably reacts with the isonitrile to generate a thio-formimidate carboxylate mixed anhydride intermediate. Applications of this chemistry to reiterative solid-phase peptide synthesis as well as solid-phase fragment coupling are described.

SUBMITTER: Wang T

PROVIDER: S-EPMC3718127 | biostudies-literature | 2013 Jul

REPOSITORIES: biostudies-literature

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Solid-phase peptide synthesis and solid-phase fragment coupling mediated by isonitriles.

Wang Ting T Danishefsky Samuel J SJ

Proceedings of the National Academy of Sciences of the United States of America 20130702 29

The synthesis of polypeptides on solid phase via mediation by isonitriles is described. The acyl donor is a thioacid, which presumably reacts with the isonitrile to generate a thio-formimidate carboxylate mixed anhydride intermediate. Applications of this chemistry to reiterative solid-phase peptide synthesis as well as solid-phase fragment coupling are described. ...[more]

PMID: 23821753

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