L-Phe-D-Oxd: a privileged scaffold for the formation of supramolecular materials

Some compounds containing the L-Phe-D-Oxd [L-Phe = L-phenylalanine; D-Oxd = (4R,5S)-4-carboxy-5-methyl oxazolidin-2-one] moiety have been prepared and their properties as supramolecular material have been checked. Some derivatives of the dipeptide L-Phe-L-Phe (that usually forms nanotubes) and some long chain derivatives that behave as low molecular weight gelators (LMWG) have been prepared. Simultaneously we have built the same structures replacing the D-Oxd moiety with a D-Pro (D-Pro = D-proline) moiety, to check if the presence of the Oxd moiety is essential for the existence of those materials: in contrast with the D-Oxd containing compounds, no material is ever formed with all the D-Pro containing molecules. This outcome suggests that the L-Phe-D-Oxd moiety may be defined as a “privileged scaffold” for the formation of supramolecular materials and can be introduced in more complex structures to induce some selected properties in the solid state.