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Naji, M. |
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Motta, Antonella |
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Aletan, Dirar |
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Mohamed, Tarek |
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Ertürk, Emre |
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Taccardi, Nicola |
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Petrov, R. H. | Madrid |
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Alshaaer, Mazen | Brussels |
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Bih, L. |
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Casati, R. |
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Muller, Hermance |
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Kočí, Jan | Prague |
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Kalteremidou, Kalliopi-Artemi | Brussels |
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Azam, Siraj |
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Ospanova, Alyiya |
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Blanpain, Bart |
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Ali, M. A. |
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Popa, V. |
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Rančić, M. |
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Ollier, Nadège |
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Azevedo, Nuno Monteiro |
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Landes, Michael |
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Rignanese, Gian-Marco |
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Mukherjee, Suprabhat
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article
Solvent‐ and Substrate‐Induced Chiroptical Inversion in Amphiphilic, Biocompatible Glycoconjugate Supramolecules: Shape‐Persistent Gelation, Self‐Healing, and Antibacterial Activity
Abstract
<jats:title>Abstract</jats:title><jats:p>We have shown solvent‐ and substrate‐dependent chiral inversion of a few glycoconjugate supramolecules. (<jats:italic>Z</jats:italic>)‐F‐Gluco, in which <jats:sc>d</jats:sc>‐glucosamine has been attached chemically to Cbz‐protected <jats:sc>l</jats:sc>‐phenylalanine at the C terminus, forms a self‐healing hydrogel through intertwining of the nanofibers wherein the gelators undergo lamellar packing in the β‐sheet secondary structures with a single chiral handedness. Dihybrid (<jats:italic>Z</jats:italic>)‐F‐gluco nanocomposite gel was prepared by in‐situ formation of silver nanoparticles AgNPs in the gel; this enhances the mechanical properties of the composite gel through physical crosslinking without altering the packing pattern. In contrast, (<jats:italic>Z</jats:italic>)‐L‐gluco bearing an <jats:sc>l</jats:sc>‐leucine moiety does not form a hydrogel but an organogel. Interestingly, the chiral handedness of the aggregates of (<jats:italic>Z</jats:italic>)‐L‐gluco can be reversed by choosing suitable solvents. In addition to self‐healing behavior, (<jats:italic>Z</jats:italic>)‐L‐gluco gel revealed shape persistency. Further, (<jats:italic>Z</jats:italic>)‐F‐gluco hydrogel is benign, nontoxic, non‐immunogenic, and non‐allergenic in animal cells. AgNP‐loaded (<jats:italic>Z</jats:italic>)‐F‐gluco hydrogel showed antibacterial activity against both Gram‐positive and Gram‐negative bacteria.</jats:p>