Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 16, Pages 3082-3088Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001643
Keywords
Supramolecular chemistry; Peptides; Fibrous materials; Proline; Scanning probe microscopy
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Funding
- Ministero dell'Universita e della Ricerca Scientifica (MIUR)
- Universita di Bologna
- Fondazione del Monte di Bologna e di Ravenna
- Consorzio InterUniversitario di Ricerca Chimica dei Metalli nei Sistemi Biologici
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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.
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