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

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 mM 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.

Pseudopeptide‐Based Hydrogels Trapping Methylene Blue and Eosin Y

“…[3][4][5][6][7][8][9] More recently the use of physical gels has been introduced, as they usually are biocompatible, [10] and may be used in medicine as scaffolds or drug-delivery systems. [11][12][13][14][15][16] In this paper we show the possibility to employt he peptidebased hydrogelator Fmoc-l-Phe-d-pGlu-OH (Fmoc = fluorenylmethyloxycarbonyl;F igure1) [17] as ad ye adsorbant. This molecule belongs to ag roup of foldamers containing the 4-car-boxy-5-methyl-oxazolidin-2-one unit (Oxd) [18] or the p-glutamic acid unit (pGlu).…”

“…For the characterization, see ref. [17] Conditions for the gel formation Ap ortion of Fmoc-l-Phe-d-pGlu-OH (10-20 mg, depending on the final concentration, ranging from 0.5 %t o2%w /w) was placed in at est tube (diameter:8mm), then MilliQ water ( % 0.95 mL) and aqueous NaOH 0.5 N( 1.0 equiv) were added and the mixture was www.chemeurj.org stirred and sonicated in turn for about 30 min, until sample dissolution. Glucono-d-lactone (GdL:1 .1 equiv) was added in one portion to the mixture.…”

Oxazolidinone‐containing pseudopeptides: Supramolecular materials, fibers, crystals, and gels

“…Recently, the gelation behavior of Fmoc‐protected dipeptides has been studied and reported . A small library of 13 molecules containing either the l ‐Phe‐ d ‐Oxd core or the isosteric l ‐Phe‐pGlu core ( p Glu = pyroglutamic acid) is shown in Figure . These molecules should behave as gelators able to form reversible gels with the phosphate‐buffered saline (PBS), that is a buffer solution commonly used in biological research.…”

“…[45][46][47][48][49] A small library of 13 Figure 13. [50] These molecules should behave as gelators able to form reversible gels with the phosphatebuffered saline (PBS), that is a buffer solution commonly used in biological research. In biomedicine, there is significant interest in exploiting self-assembly to construct mimics of the extracellular matrix (ECM) for cell-culture applications.…”

Enzymatic synthesis of mannitol dioctanoate and its utilisation in the preparation of structured edible oil

“…Gelled oil can be defined as liquid oil entrapped within a thermo-reversible, three-dimensional gelling network. The gelling network is often formed by hydrophobic liquid and low concentration of organogelator molecules which are mostly low molecular weight compounds (Hughes et al, 2009;Grassi et al, 2011;Milli et al, 2014).…”