ArticleJournal of the American Chemical Society2025
Mechanism of C-3 Acyl Neighboring Group Participation in Mannuronic Acid Glycosyl Donors.
Article in Journal of the American Chemical Society, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Stereoselectivity of Galactosylation Reactions In Vacuo.Journal of the American Chemical Society · 2026Article
- Synthesis and In Vivo Antifungal Evaluation of 3-Acyl-bromoindole Regioisomers: A Multi-Targeting Study on Postharvest Pathogen Control and Molecular Dynamics.Antibiotics (Basel, Switzerland) · 2026Article
- 3-Deoxy-3-Fluoro Mannuronic Acid Alginates: Stereoselective Automated Synthesis and Conformational Behaviour.Angewandte Chemie (International ed. in English) · 2026Article
- Elucidating the Stereodirecting Effect of C-4 Acyl Groups on Galactosyl Donors.Angewandte Chemie (International ed. in English) · 2026Article
- Detecting glycosyl-oxonium and glycosyl-nitrilium ions using exchange NMR to investigate solvent effects in glycosylation reactions.Nature communications · 2026Article
- Mechanism of 3-The Journal of organic chemistry · 2025Article
- Elucidating the Curtin-Hammett Principle in Glycosylation Reactions: The Decisive Role of Equatorial Glycosyl Triflates.Journal of the American Chemical Society · 2025Article
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Authors and funding
12 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
One of the main challenges in oligosaccharide synthesis is the stereoselective introduction of the glycosidic bond. In order to understand and control glycosylation reactions, thorough mechanistic studies are required. Reaction intermediates found by NMR spectroscopy often cannot explain the glycosylation's stereochemical outcome. Hence, reactions may proceed through low-abundance reaction intermediates that are difficult to detect, according to a Curtin-Hammett scenario. We have previously observed that manno-type sugars can engage in C-3 acyl neighboring group participation. Herein, we report the detection of glycosyl dioxanium ions that result from C-3 neighboring group participation in mannuronic acid donors. Using a suite of exchange NMR techniques, we were able to dissect the kinetics of the conformational ring-flip that precedes C-3 acyl participation and the participation event itself in various manno-type sugars. Hence, this study provides a complete picture of mannosyl dioxanium ion formation.
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Registered trials
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