Multicomponent Reactions of Isocyanides for the Preparation of Low Molecular Weight Gelators: Preliminary Studies

Ramiro, José Luis; Marcos, Carlos F.; Neo, Ana G.

doi:10.3390/ecsoc-25-11668

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2024

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“…On the other hand, the exploitation of peptidomimetics as supramolecular gelators could be hampered by their sometimes-difficult synthesis. As a result, there is a growing interest in obtaining gelator molecules through few synthetic steps, and in using non-expensive starting materials [21,22].…”

Section: Introductionmentioning

confidence: 99%

Stereochemical Behavior of Pyrrolo-Pyrazole Peptidomimetics Promoting Phase-Selective Supramolecular Organogels

Chiesa,

Anastasi,

Clerici

et al. 2024

Gels

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Supramolecular gels were developed by taking advantage of an assembly of small dipeptides containing pyrrolo-pyrazole scaffolds. The dipeptides were prepared through a robust and ecofriendly synthetic approach from the commercially available starting materials of diazoalkanes and maleimides. By playing with the functionalization of the scaffold, the choice of the natural amino acid, and the stereochemistry, we were able to obtain phase-selective gels. In particular, one peptidomimetic showed gelation ability and thermoreversibility in aromatic solvents at very low concentrations. Rheology tests showed a typical viscoelastic solid profile, indicating the formation of strong gels that were stable under high mechanical deformation. NMR studies were performed, allowing us to determine the conformational and stereochemical features at the base of the supramolecular interactions.

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Section: Introductionmentioning

confidence: 99%