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 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. 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 materialshave been determined. Some L-Phe-L-Phe dipeptide derivatives form nanotubes and other long-chain derivatives behave as gels. The effect of the D-Oxd moiety on the properties of the material was investigated. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.