New fluorinated peptidomimetics through tandem aza-michael addition to α-trifluoromethyl acrylamide acceptors: synthesis and conformational study in solid state and solution

Santos Fustero, Gema Chiva, Julio Piera, Juan F Sanz-Cervera, Alessandro Volonterio, Matteo Zanda, Carmen Ramirez de Arellano

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Abstract

A range of partially modified retro (PMR) psi[NHCH(2)] peptide mimetics containing a hydrolytically stable CH(2)CH(CF(3))CO unit have been synthesized. The first kind of peptidomimetics is obtained from the highly efficient aza-Michael addition of different amines to alpha-trifluoromethyl acrylamide acceptors. Subsequent deprotection of the amino group furnishes the key common intermediate for the synthesis of other families of peptidomimetics: dipeptides, tripeptides, peptidomimetics containing a urea moiety, and structures containing two units of alpha-trifluoromethyl-beta(2)-alanine. Finally, a conformational study of several of the newly synthesized peptidomimetics, performed with the aid of X-ray analysis and NMR techniques, shows a beta-turn-like conformation for the structures both in the solid state and in solution.
Original languageEnglish
Pages (from-to)3122-3132
Number of pages11
JournalJournal of Organic Chemistry
Volume74
Issue number8
Early online date23 Mar 2009
DOIs
Publication statusPublished - 17 Apr 2009

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Keywords

  • acrylamides
  • alanine
  • aza compounds
  • crystallography, x-ray
  • fluorine compounds
  • magnetic resonance spectroscopy
  • molecular conformation
  • peptides
  • solutions

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