Christina Forbes - Synthesis of Thiophenylalanine-containing Peptides via Cu(I)-mediated Cross-Coupling

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  Publication Details (including relevant citation   information):

  Forbes, C. R.; Zondlo, N. J. Org. Lett.,   2012, 14 (2), 464-467.


  Aryl thiolates have unique reactive, redox, electronic, and   spectroscopic properties. A practical approach to synthesize   peptides containing thiophenylalanine has been developed via a   novel Cu(I)-mediated cross-coupling reaction between thiolacetic   acid and iodophenylalanine-containing peptides in the solid   phase. This approach is compatible with all canonical   proteinogenic functional groups, providing general access to aryl   thiolates in peptides. Peptides containing thiophenylalanine   (pKa 6.4) were readily elaborated to contain   methyl, allyl, and nitrobenzyl thioethers, disulfides,   sulfoxides, sulfones, or sulfonates.

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