ArticleNature communications2018
Unravelling the structure of glycosyl cations via cold-ion infrared spectroscopy.
Article in Nature communications, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 34 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
34 citing papers in PubMed.
- Stereoselectivity of Galactosylation Reactions In Vacuo.Journal of the American Chemical Society · 2026Article
- Beyond the two-conformer model: boat conformers provide stereoselectivity in SChemical science · 2026Article
- Evaluating Participation Modes in Peracetylated Glycosyl Cations.Organic letters · 2026Article
- How to Use Quantum Chemistry for Analyzing Mass Spectrometry Data.Mass spectrometry (Tokyo, Japan) · 2026Review
- Distinguishing Isomeric Caffeine Metabolites through Protomers and Tautomers Using Cryogenic Gas-Phase Infrared Spectroscopy.Analytical chemistry · 2025Article
- Examining the Effect of an Anion-Binding Reagent on the Structure of Deprotonated Leucine Enkephalin Using Cryogenic-Ion Infrared Action Spectroscopy.The journal of physical chemistry. A · 2025Article
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates.Molecules (Basel, Switzerland) · 2025Article
- Advanced Mass Spectrometry Techniques for the Characterization of Carbohydrates.Handbook of experimental pharmacology · 2025Review
- Reinvestigation of the internal glycan rearrangement of Lewis a and blood group type H1 epitopes.Physical chemistry chemical physics : PCCP · 2024Article
- Characterization of elusive rhamnosyl dioxanium ions and their application in complex oligosaccharide synthesis.Nature communications · 2024Article
- Mechanistic insight into benzylidene-directed glycosylation reactions using cryogenic infrared spectroscopy.Nature synthesis · 2024Article
- Detection and Characterization of Rapidly Equilibrating Glycosylation Reaction Intermediates Using Exchange NMR.Journal of the American Chemical Society · 2023Article
- Unraveling the promoter effect and the roles of counterion exchange in glycosylation reaction.Science advances · 2023Article
- Decoding the Fucose Migration Product during Mass-Spectrometric analysis of Blood Group Epitopes.Angewandte Chemie (International ed. in English) · 2023Article
- Characterization and Fate of a Septanosyl Ferrier Cation in the Gas and Solution Phases.The Journal of organic chemistry · 2023Article
- Competing C-4 and C-5-Acyl Stabilization of Uronic Acid Glycosyl Cations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- The Influence of the Electron Density in Acyl Protecting Groups on the Selectivity of Galactose Formation.Journal of the American Chemical Society · 2022Article
- Stabilization of Glucosyl Dioxolenium Ions by "Dual Participation" of the 2,2-Dimethyl-2-(The Journal of organic chemistry · 2022Article
- Small tools for sweet challenges: advances in microfluidic technologies for glycan synthesis.Analytical and bioanalytical chemistry · 2022Review
Corrections and comments
- Erratum issued
Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Glycosyl cations are the key intermediates during the glycosylation reaction that covalently links building blocks during the synthetic assembly of carbohydrates. The exact structure of these ions remained elusive due to their transient and short-lived nature. Structural insights into the intermediate would improve our understanding of the reaction mechanism of glycosidic bond formation. Here, we report an in-depth structural analysis of glycosyl cations using a combination of cold-ion infrared spectroscopy and first-principles theory. Participating C2 protective groups form indeed a covalent bond with the anomeric carbon that leads to C1-bridged acetoxonium-type structures. The resulting bicyclic structure strongly distorts the ring, which leads to a unique conformation for each individual monosaccharide. This gain in mechanistic understanding fundamentally impacts glycosynthesis and will allow to tailor building blocks and reaction conditions in the future.
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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.