A range of partially modified retro (PMR) ψ[NHCH2] peptide mimetics containing a hydrolytically stable CH2CH(CF3)CO unit have been synthesized. The first kind of peptidomimetics is obtained from the highly efficient aza-Michael addition of different amines to R-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 R-trifluoromethyl-beta2-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.
New Fluorinated Peptidomimetics through Tandem Aza-Michael Addition to alfa-Trifluoromethyl Acrilamide Acceptors: Synthesis and Conformational Study in Solid State and Solution
VOLONTERIO, ALESSANDRO;
2009-01-01
Abstract
A range of partially modified retro (PMR) ψ[NHCH2] peptide mimetics containing a hydrolytically stable CH2CH(CF3)CO unit have been synthesized. The first kind of peptidomimetics is obtained from the highly efficient aza-Michael addition of different amines to R-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 R-trifluoromethyl-beta2-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.File | Dimensione | Formato | |
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J. Org. Chem. 2009, 3122-3132.pdf
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