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Updated: Mar 1, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
Assembly and inhibitory activity of monovalent mannosides terminated with aromatic methyl esters: The effect of
Hussein Al-Mughaid1, Raed M Al-Zoubi2, Maha Khazaaleh2
1Department of Chemistry, Jordan University of Science and Technology, PO Box 3030, Irbid 22110, Jordan; Department of Chemistry, Dalhousie University, Halifax, NS, B3H 4J3, Canada.
Abstract:
A series of monovalent α-D-mannoside ligands terminated with aromatic methyl esters have been synthesized in excellent yields using the Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click chemistry"). These mannosides were designed to have a unique aglycone moiety (tail) that combines a triazole ring attached to aromatic methyl esters via a six carbon alkyl chain. The mannose unit of these ligands was linked at the ortho, meta, and para positions of substituted methyl benzoates and 1-, 3-, and 6-substituted methyl 2-napthaoates. In hemagglutination assays, ligands (32A-38A) showed better inhibitory activities than the standard inhibitor, methyl α-D-mannopyranoside. Overall, the naphthyl-based mannoside ligand (37A) showed the best activity and therefore merits further development.
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