Dokument: A Modular Solid Phase Synthesis Approach for Glycocalix[4]Arene Derivatives and Their Multivalent Presentation on Ultrasmall Gold Nanoparticles.
| Titel: | A Modular Solid Phase Synthesis Approach for Glycocalix[4]Arene Derivatives and Their Multivalent Presentation on Ultrasmall Gold Nanoparticles. | |||||||
| URL für Lesezeichen: | https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=70323 | |||||||
| URN (NBN): | urn:nbn:de:hbz:061-20250724-120231-3 | |||||||
| Kollektion: | Publikationen | |||||||
| Sprache: | Englisch | |||||||
| Dokumententyp: | Wissenschaftliche Texte » Artikel, Aufsatz | |||||||
| Medientyp: | Text | |||||||
| Autoren: | Kayser, Alisa [Autor] Klein, Kai [Autor] Babushkina, Daria [Autor] Sakse, Anne [Autor] Mouafo Kenne, Gisele [Autor] Gerling-Driessen, Ulla I.M. [Autor] Tabatabai, Monir [Autor] Epple, Matthias [Autor] Hartmann, Laura [Autor] | |||||||
| Dateien: |
| |||||||
| Stichwörter: | multivalency, E. coli, bacterial inhibition, glycocalix[n]arenes, gold nanoparticles | |||||||
| Beschreibung: | Gold nanoparticles and calix[n]arenes are well-established
platforms for creating multivalent carbohydrate ligands that enhance binding avidity and selectivity toward carbohydraterecognizing receptors, such as bacterial lectins. In this study, we present a modular synthesis protocol for tailor-made and (multi)functional glycocalix[4]arene derivatives using solid-phase polymer synthesis. A calix[4]arene building block with a single carboxyl group on the lower rim and four nitro groups at the upper rim is introduced. This building block is attached to a solid support using standard solid phase peptide coupling conditions, followed by reduction of the upper rim nitro functionalities to yield four amine groups, that are further functionalized through solid-phase polymer synthesis. Using this modular approach, we access a series of glyco-calix[4]arene structures that are then further conjugated onto ultrasmall gold nanoparticles. Conjugation is promoted either via one or via four alkyne groups on the glycocalixarene structure, providing a handle to tune the overall valency of the final glyco[4]calixarene-gold nanoparticle conjugates. Finally, the glycocalix[4]arene derivatives and conjugates are evaluated for their inhibitory potential against bacterial adhesion showing the importance of multivalent carbohydrate presentation to effectively block Escherichia coli (E.coli) adhesion. | |||||||
| Rechtliche Vermerke: | Originalveröffentlichung:
Kayser, A., Klein, K., Babushkina, D., Sakse, A., Mouafo Kenne, G., Gerling‐Driessen, U. I. M., Tabatabai, M., Epple, M., & Hartmann, L. (2025). A Modular Solid Phase Synthesis Approach for Glycocalix[4]Arene Derivatives and Their Multivalent Presentation on Ultrasmall Gold Nanoparticles. Chemistry - a European Journal, 31(40), Article e202500497. https://doi.org/10.1002/chem.202500497 | |||||||
| Lizenz: |  Dieses Werk ist lizenziert unter einer Creative Commons Namensnennung 4.0 International Lizenz | |||||||
| Fachbereich / Einrichtung: | Mathematisch- Naturwissenschaftliche Fakultät | |||||||
| Dokument erstellt am: | 24.07.2025 | |||||||
| Dateien geändert am: | 24.07.2025 |
