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Article Dans Une Revue Organic Letters Année : 2016

Native Chemical Ligation Strategy to Overcome Side Reactions during Fmoc-Based Synthesis of C-Terminal Cysteine-Containing Peptides

Résumé

The Fmoc-based solid phase synthesis of C-terminal cysteine-containing peptides is problematic, due to side reactions provoked by the pronounced acidity of the Calpha proton of cysteine esters. We herein describe a general strategy consisting of the postsynthetic introduction of the C-terminal Cys through a key chemoselective native chemical ligation reaction with N-Hnb-Cys peptide crypto-thioesters. This method was successfully applied to the demanding peptide sequences of two natural products of biological interest, giving remarkably high overall yields compared to that of a state of the art strategy.
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Dates et versions

hal-01407492 , version 1 (02-12-2016)

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Dominique Lelièvre, Victor P. Terrier, Agnès F. Delmas, Vincent Aucagne. Native Chemical Ligation Strategy to Overcome Side Reactions during Fmoc-Based Synthesis of C-Terminal Cysteine-Containing Peptides. Organic Letters, 2016, 18 (5), pp.920 - 923. ⟨10.1021/acs.orglett.5b03612⟩. ⟨hal-01407492⟩
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