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

Abstract : 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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https://hal.archives-ouvertes.fr/hal-01407492
Contributor : Isabelle Frapart <>
Submitted on : Friday, December 2, 2016 - 11:44:38 AM
Last modification on : Tuesday, June 4, 2019 - 4:30:08 PM

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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, American Chemical Society, 2016, 18 (5), pp.920 - 923. ⟨10.1021/acs.orglett.5b03612⟩. ⟨hal-01407492⟩

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