ArticleChemistry (Weinheim an der Bergstrasse, Germany)2026
Synthesis and Glycosidase Inhibition Studies of Novel Exoglycals Targeting GH3 Family Enzymes: Insights from Comparative Analysis with Macrolide Antibiotics.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Glycosidases are key enzymes involved in carbohydrate metabolism. Members of the GH3 family have emerged as therapeutic targets due to their roles in natural product biosynthesis and disease. Transition-state analogues represent a powerful strategy for glycosidase inhibition, and exoglycals (C-glycosylidenes) have gained interest as conformational mimics of glycosidic bond hydrolysis. Herein, we report the synthesis of novel exoglycals bearing diverse substituents, including terminal alkynes and thymidyl residues, via a modified Julia-olefination strategy from sugar-derived lactones and substituted sulfones. Selected alkyne-containing exoglycals were further functionalized through cycloaddition with azidothymidine. Inhibition studies against EryBI, a GH3 glycosyl hydrolase, were performed. Kinetic analysis revealed diverse inhibitory mechanisms among the exoglycals, displaying competitive inhibition, with K
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