Solvent- and Substrate-Induced Chiroptical Inversion in Amphiphilic, Biocompatible Glycoconjugate Supramolecules: Shape-Persistent Gelation, Self-Healing, and Antibacterial Activity

Autor: Angshuman Ghosh, Soumen Kumar Dubey, Maxcimilan Patra, Jishu Mandal, Narendra Nath Ghosh, Priyanka Das, Arpita Bhowmick, Keka Sarkar, Suprabhat Mukherjee, Rajat Saha, Subham Bhattacharjee
Rok vydání: 2022
Předmět:
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany). 28(63)
ISSN: 1521-3765
Popis: We have shown solvent- and substrate-dependent chiral inversion of a few glycoconjugate supramolecules. (Z)-F-Gluco, in which d-glucosamine has been attached chemically to Cbz-protected l-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 (Z)-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, (Z)-L-gluco bearing an l-leucine moiety does not form a hydrogel but an organogel. Interestingly, the chiral handedness of the aggregates of (Z)-L-gluco can be reversed by choosing suitable solvents. In addition to self-healing behavior, (Z)-L-gluco gel revealed shape persistency. Further, (Z)-F-gluco hydrogel is benign, nontoxic, non-immunogenic, and non-allergenic in animal cells. AgNP-loaded (Z)-F-gluco hydrogel showed antibacterial activity against both Gram-positive and Gram-negative bacteria.
Databáze: OpenAIRE
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