Synthesis and NMR elucidation of novel tetrapeptides

The synthesis and NMR elucidation of Ala-Val-Pro-Ile and five novel peptide-based derivatives are reported. These peptides mimic the natural second mitochondria-derived activator of caspase (Smac) protein. Purification was achieved using preparative HPLC and the NMR elucidation of all compounds is reported for the first time. A series of overlapping signals were observed in the 1D NMR spectra thus making assignment a difficult task to undertake. The use of 2D NMR techniques with the inclusion of efficient adiabatic symmetrized ROESY proved to be an effective tool in overcoming these difficulties. Copyright (C) 2011 European Peptide Society and John Wiley & Sons, Ltd.