ArticleJournal of the American Chemical Society2023
Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Chemical exchange saturation transfer NMR: An analytical tool and its applications.Magnetic resonance letters · 2026Review
- 3-Deoxy-3-Fluoro Mannuronic Acid Alginates: Stereoselective Automated Synthesis and Conformational Behaviour.Angewandte Chemie (International ed. in English) · 2026Article
- Anomer-Selective Vorbrüggen Reaction for the Catalytic Synthesis of CJournal of the American Chemical Society · 2026Article
- Evaluating Participation Modes in Peracetylated Glycosyl Cations.Organic letters · 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
- Synthesis ofScience advances · 2025Article
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- The Stereoselectivity of Neighboring Group-Directed Glycosylation Is Concentration-Dependent.Journal of the American Chemical Society · 2025Article
- Mechanism of C-3 Acyl Neighboring Group Participation in Mannuronic Acid Glycosyl Donors.Journal of the American Chemical Society · 2025Article
- Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates.Molecules (Basel, Switzerland) · 2025Article
- Development of a Cryogenic Flow Reactor to Optimize Glycosylation Reactions Based on the Active Donor Intermediate.Organic process research & development · 2024Article
- Characterization of elusive rhamnosyl dioxanium ions and their application in complex oligosaccharide synthesis.Nature communications · 2024Article
- Anomeric Triflates versus Dioxanium Ions: Different Product-Forming Intermediates from 3-Acyl Benzylidene Mannosyl and Glucosyl Donors.The Journal of organic chemistry · 2024Article
- Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy.Nature synthesis · 2024Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 2023Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The stereoselective introduction of glycosidic bonds (glycosylation) is one of the main challenges in the chemical synthesis of carbohydrates. Glycosylation reaction mechanisms are difficult to control because, in many cases, the exact reactive species driving product formation cannot be detected and the product outcome cannot be explained by the primary reaction intermediate observed. In these cases, reactions are expected to take place via other low-abundance reaction intermediates that are in rapid equilibrium with the primary reaction intermediate via a Curtin-Hammett scenario. Despite this principle being well-known in organic synthesis, mechanistic studies investigating this model in glycosylation reactions are complicated by the challenge of detecting the extremely short-lived reactive species responsible for product formation. Herein, we report the utilization of the chemical equilibrium between low-abundance reaction intermediates and the stable, readily observed α-glycosyl triflate intermediate in order to infer the structure of the former species by employing exchange NMR. Using this technique, we enabled the detection of reaction intermediates such as β-glycosyl triflates and glycosyl dioxanium ions. This demonstrates the power of exchange NMR to unravel reaction mechanisms as we aim to build a catalog of kinetic parameters, allowing for the understanding and eventual prediction of glycosylation reactions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.