ArticleNature communications2020
Characterization of glycosyl dioxolenium ions and their role in glycosylation reactions.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 51 papers.
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Who cites it
51 citing papers in PubMed, 122 citations in OpenAlex.
- 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
- A syntheticScience advances · 2026Article
- How to Use Quantum Chemistry for Analyzing Mass Spectrometry Data.Mass spectrometry (Tokyo, Japan) · 2026Review
- Anion-Assisted Glycosylation of Galactose: A Computational Study.The Journal of organic chemistry · 2025Article
- Comprehensive synthesis and anticoagulant evaluation of a diverse fucoidan library.Nature communications · 2025Article
- Elucidating reactive sugar-intermediates by mass spectrometry.Communications chemistry · 2025Review
- Neighboring-Group Participation by a Less Electron-Donating, Participating C-2-Ester Ensures Higher 1,2-The Journal of organic chemistry · 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
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
- Diastereoselective Substitution Reactions of Acyclic Acetals Controlled by Remote Participation of an Acyloxy Group.Organic letters · 2024Article
- Microfluidics-Based Ionic Catch and Release Oligosaccharide Synthesis (ICROS-Microflow) to Expedite Glycosylation Chemistry.JACS Au · 2024Article
- Acetal Substitution Reactions: Stereoelectronic Effects, Conformational Analysis, Reactivity vs. Selectivity, and Neighboring-Group Participation.Synlett : accounts and rapid communications in synthetic organic chemistry · 2024Article
- Article
- 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
- 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
Corrections and comments
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Authors and funding
17 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Controlling the chemical glycosylation reaction remains the major challenge in the synthesis of oligosaccharides. Though 1,2-trans glycosidic linkages can be installed using neighboring group participation, the construction of 1,2-cis linkages is difficult and has no general solution. Long-range participation (LRP) by distal acyl groups may steer the stereoselectivity, but contradictory results have been reported on the role and strength of this stereoelectronic effect. It has been exceedingly difficult to study the bridging dioxolenium ion intermediates because of their high reactivity and fleeting nature. Here we report an integrated approach, using infrared ion spectroscopy, DFT computations, and a systematic series of glycosylation reactions to probe these ions in detail. Our study reveals how distal acyl groups can play a decisive role in shaping the stereochemical outcome of a glycosylation reaction, and opens new avenues to exploit these species in the assembly of oligosaccharides and glycoconjugates to fuel biological research.
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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.