<scp>L</scp>‐Phe‐<scp>D</scp>‐Oxd: A Privileged Scaffold for the Formation of Supramolecular Materials

Abstract

Abstract Some compounds containing the L ‐Phe‐ D ‐Oxd [ L ‐Phe = L ‐phenylalanine; D ‐Oxd = (4 R ,5 S )‐4‐carboxy‐5‐methyl oxazolidin‐2‐one] moiety have been prepared and their properties as supramolecular material have been determined. Some derivatives of the dipeptide L ‐Phe‐ L ‐Phe (which usually forms nanotubes) and some long‐chain derivatives that behave as low‐molecular‐weight gelators have been prepared. We have also replaced the D ‐Oxd moiety with a D ‐Pro ( D ‐Pro = D ‐proline) moiety to check if the presence of the Oxd moiety was essential for the existence of those materials. In contrast to the D ‐Oxd‐containing compounds, no material was ever formed with any of 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 it can be introduced into more complex structures to induce some selected properties in the solid state.