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 language | English |
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Pages (from-to) | 3122-3132 |
Number of pages | 11 |
Journal | Journal of Organic Chemistry |
Volume | 74 |
Issue number | 8 |
Early online date | 23 Mar 2009 |
DOIs | |
Publication status | Published - 17 Apr 2009 |
Keywords
- acrylamides
- alanine
- aza compounds
- crystallography, x-ray
- fluorine compounds
- magnetic resonance spectroscopy
- molecular conformation
- peptides
- solutions