Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction

Julien Tailhades, Marie Aude Gidel, Benjamin Grossi, Jennifer Lécaillon, Luc Brunel, Gilles Subra, Jean Martinez, Muriel Amblard

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33 Citations (Scopus)

Abstract

Getting the better of troublemakers: C-terminal peptide alcohols cannot be synthesized by conventional solidphase peptide synthesis (SPPS) because of the absence of a free carboxylic group to attach to the resin. This problem was circumvented by anchoring a β-amino alcohol residue to the resin to provide a starting point for SPPS. An intramolecular O-N acyl shift completed the synthesis of the desired peptides (see scheme). 

Original languageEnglish
Pages (from-to)117-120
Number of pages4
JournalAngewandte Chemie - International Edition
Volume49
Issue number1
DOIs
Publication statusPublished - 4 Jan 2010
Externally publishedYes

Keywords

  • Isopeptides
  • Mitsunobu reaction
  • O-n acyl shift
  • Peptide alcohols
  • Solid-phase synthesis

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