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Turning Around the L ‐Phe‐ D ‐Oxd Moiety for a Versatile Low‐Molecular‐Weight Gelator
Author(s) -
Milli Lorenzo,
Castellucci Nicola,
Tomasini Claudia
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402787
Subject(s) - chemistry , moiety , supramolecular chemistry , molecule , solvent , phosphate buffered saline , peptidomimetic , scaffold , combinatorial chemistry , small molecule , stereochemistry , organic chemistry , biochemistry , chromatography , peptide , biomedical engineering , medicine
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.