ArticleNature chemistry2012
Dissecting the mechanisms of a class of chemical glycosylation using primary ¹³C kinetic isotope effects.
Article in Nature chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 55 papers.
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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.
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Who cites it
55 citing papers in PubMed.
- Stereoselectivity of Galactosylation Reactions In Vacuo.Journal of the American Chemical Society · 2026Article
- Iron-Catalyzed Highly Stereospecific Glycosylation with Glycal Epoxides.Angewandte Chemie (International ed. in English) · 2025Article
- 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
- 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
- Modeling of the Carbohydrate Oxacarbenium Ionic Intermediates of Glycosylation Reactions with Explicit Account for Protective Group Effects.ACS omega · 2025Article
- Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates.Molecules (Basel, Switzerland) · 2025Article
- Acetal Substitution Reactions: Stereoelectronic Effects, Conformational Analysis, Reactivity vs. Selectivity, and Neighboring-Group Participation.Synlett : accounts and rapid communications in synthetic organic chemistry · 2024Article
- Development of a Cryogenic Flow Reactor to Optimize Glycosylation Reactions Based on the Active Donor Intermediate.Organic process research & development · 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
- Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.Chemical reviews · 2022Review
- Recent Advances in Stereoselective ChemicalFrontiers in molecular biosciences · 2022Review
- Glycosyl Sulfonates Beyond Triflates.Chemical record (New York, N.Y.) · 2021Review
- Guidelines forACS central science · 2021Article
- A Mechanistic Probe into 1,2-Advanced synthesis & catalysis · 2021Article
- Total Synthesis of theOrganic letters · 2021Article
- Glycosyl Oxocarbenium Ions: Structure, Conformation, Reactivity, and Interactions.Accounts of chemical research · 2021Review
Corrections and comments
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Authors and funding
6 authors.
Funding
Abstract
Although arguably the most important reaction in glycoscience, chemical glycosylations are among the least well understood of organic chemical reactions, resulting in an unnecessarily high degree of empiricism and a brake on rational development in this critical area. To address this problem, primary (13)C kinetic isotope effects have now been determined for the formation of β- and α-manno- and glucopyranosides using a natural abundance NMR method. In contrast to the common current assumption, for three of the four cases studied the experimental and computed values are indicative of associative displacement of the intermediate covalent glycosyl trifluoromethanesulfonates. For the formation of the α-mannopyranosides, the experimentally determined KIE differs significantly from that computed for an associative displacement, which is strongly suggestive of a dissociative mechanism that approaches the intermediacy of a glycosyl oxocarbenium ion. The application of analogous experiments to other glycosylation systems should shed further light on their mechanisms and thus assist in the design of better reactions conditions with improved stereoselectivity.
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