Conformations of psi [CH2NH] pseudopeptides. Cyclo[Gly-Pro psi [CH2NH]Gly-D-Phe-Pro]-TFA and cyclo[Gly-Pro psi [CH2NH]Gly-D-Phe-Pro].

Abstract

The cyclic pseudopentapeptide cyclo[Gly-Pro psi [CH2NH]Gly-D-Phe-Pro] and its TFA salt were synthesized by solution methods, and their conformations were studied by NMR spectroscopy in both DMSO-d6 and CDCl3. While intramolecular hydrogen bonding is observed with some conformers, the nature of the solvent and the presence of TFA affects the relative structural rigidities of the compounds. No evidence was found for the psi [CH2NH] or psi [CH2NH2+] units acting as H donors in this series.