Related Experiment Video
Updated: Apr 3, 2026
09:44
Design, Synthesis, and Photochemical Properties of Clickable Caged Compounds
Published on: October 15, 2019
13.1K
Unique tetrameric and hexameric mannoside clusters prepared by click chemistry
Hussein Al-Mughaid1, Raed M Al-Zoubi2, Nawal K Paul3
1Department of Chemistry, Dalhousie University, Halifax, NS B3H 4J3, Canada; Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan.
Carbohydrate Research
|September 24, 2015
Summary
Novel mannoside clusters were synthesized to inhibit uropathogenic Escherichia coli. These compounds, featuring triazole linkages and a specific aglycone length, show good water solubility after deprotection, indicating potential therapeutic applications.
Area of Science:
- Carbohydrate Chemistry
- Medicinal Chemistry
- Microbiology
Background:
- Uropathogenic *Escherichia coli* (UPEC) poses a significant health threat.
- Mannoside clusters are explored as potential inhibitors of bacterial adhesion.
- Targeting bacterial lectins, like those on UPEC, is a promising therapeutic strategy.
Purpose of the Study:
- To synthesize novel tetrameric and hexameric mannoside clusters.
- To evaluate these clusters as potential inhibitors of UPEC.
- To design clusters with aglycones tailored for specific bacterial binding sites.
Main Methods:
- Cu(I)-catalyzed azide-alkyne cycloaddition (click chemistry) for cluster synthesis.
- Synthesis of tetrameric and hexameric mannoside structures.
- Deprotection of acetylated mannosides to yield soluble compounds.
Main Results:
- Successfully synthesized novel tetrameric and hexameric mannoside clusters.
- Incorporated 1,2,3-triazole linkages using click chemistry.
- Achieved good water solubility for de-O-acetylated mannoside clusters.
Conclusions:
- The synthesized mannoside clusters are water-soluble and structurally defined.
- The aglycone length is optimized for potential interaction with the tyrosine gate of UPEC.
- These compounds represent promising candidates for further investigation as UPEC inhibitors.
