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.
- aza compounds
- crystallography, x-ray
- fluorine compounds
- magnetic resonance spectroscopy
- molecular conformation
Fustero, S., Chiva, G., Piera, J., Sanz-Cervera, J. F., Volonterio, A., Zanda, M., & Ramirez de Arellano, C. (2009). New fluorinated peptidomimetics through tandem aza-michael addition to α-trifluoromethyl acrylamide acceptors: synthesis and conformational study in solid state and solution. Journal of Organic Chemistry, 74(8), 3122-3132. https://doi.org/10.1021/jo9001867