Turning Around the <scp>L</scp>‐Phe‐<scp>D</scp>‐Oxd Moiety for a Versatile Low‐Molecular‐Weight Gelator

Abstract

Abstract We have prepared a small library of 13 peptidomimetics containing the L ‐Phe‐ D ‐Oxd unit (or the isosteric L ‐Phe‐ D ‐pGlu unit), which is a privileged scaffold for the preparation of supramolecular materials. These compounds were prepared in solution in excellent yields and tested as organogelators and/or hydrogelators at 10 m M concentration with a plethora of solvents and solvent mixtures. Two molecules were very efficient gelators: one is a organogelator and the other is a hydrogelator. As these compounds have quite different skeletons, a rationale to explain the different behaviour of these molecules as gelators takes into consideration their hydrophobicity, expressed as log P . Finally, Fmoc‐ L ‐Phe‐ D ‐pGlu‐OH ( 6b ) efficiently gelated phosphate‐buffered saline (PBS 1X) at 1.5 % w/w concentration and is an excellent candidate for the preparation of novel materials for applications in, for example, drug release, biological assays, and tissue engineering.