ArticleJournal of the American Chemical Society2013
Influence of side chain conformation and configuration on glycosyl donor reactivity and selectivity as illustrated by sialic acid donors epimeric at the 7-position.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
- The effect of neighbouring group participation and possible long range remote group participation inBeilstein journal of organic chemistry · 2025Review
- Beyond Traditional Stimuli: Exploring Salt-Responsive Bottlebrush Polymers-Trends, Applications, and Perspectives.ACS omega · 2024Review
- Comparison of glycosyl donors: a supramer approach.Beilstein journal of organic chemistry · 2024Article
- Influence of Side Chain Conformation on the Activity of Glycosidase Inhibitors.Angewandte Chemie (International ed. in English) · 2023Article
- Primary Structure of Glycans by NMR Spectroscopy.Chemical reviews · 2023Review
- Influence of Configuration at the 4- and 6-Positions on the Conformation and Anomeric Reactivity and Selectivity of 7-Deoxyheptopyranosyl Donors: Discovery of a Highly Equatorially Selective l-The Journal of organic chemistry · 2021Article
- GH47 and Other Glycoside Hydrolases Catalyze Glycosidic Bond Cleavage with the Assistance of Substrate Super-arming at the Transition State.ACS catalysis · 2021Article
- Influence of substitution at the 5α-Position on the side chain conformation of glucopyranosides.Carbohydrate research · 2021Article
- En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.Journal of the American Chemical Society · 2021Article
- Predictive Analysis of the Side Chain Conformation of the Higher Carbon Sugars: Application to the Preorganization of the Aminoglycoside Ring 1 Side Chain for Binding to the Bacterial Ribosomal Decoding A Site.The Journal of organic chemistry · 2020Article
- Glycoside Hydrolases Restrict the Side Chain Conformation of Their Substrates To Gain Additional Transition State Stabilization.Journal of the American Chemical Society · 2020Article
- Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.Carbohydrate research · 2020Article
- Mechanisms of Stereodirecting Participation and Ester Migration from Near and Far in Glycosylation and Related Reactions.Chemical reviews · 2020Article
- Stereocontrolled Synthesis of the Equatorial Glycosides of 3-Deoxy-d-manno-oct-2-ulosonic Acid: Role of Side Chain Conformation.Journal of the American Chemical Society · 2020Article
- Synthesis of glycoimmunogen Tn-Thr-PS A1Journal of carbohydrate chemistry · 2020Article
- Use of Phenols as Nucleophiles in the Zbiral Oxidative Deamination ofThe Journal of organic chemistry · 2019Article
- Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.Journal of the American Chemical Society · 2018Article
- Article
- The Experimental Evidence in Support of Glycosylation Mechanisms at the SChemical reviews · 2018Review
- Interplay of Protecting Groups and Side Chain Conformation in Glycopyranosides. Modulation of the Influence of Remote Substituents on Glycosylation?The Journal of organic chemistry · 2018Article
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2 authors.
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Abstract
Two N-acetyl 4O,5N-oxazolidinone-protected sialyl thioglycosides epimeric at the 7-position have been synthesized and their reactivity and stereoselectivity in glycosylation reactions have been compared. It is demonstrated that the natural 7S-donor is both more reactive and more α-selective than the unnatural 7R-isomer. The difference in reactivity is attributed to the side chain conformation and specifically to the proximity of O7 to the anomeric center. In the natural 7S-isomer, O7 is closer to the anomeric center than in its unnatural 7R-epimer and, therefore, better able to support incipient positive charge at the locus of reaction. The difference in selectivity is also attributed to the side conformation, which in the unnatural 7R-series is placed perpendicularly above the α-face of the donor and so shields it to a greater extent than in the 7S-series. These observations are consistent with earlier conclusions on the influence of the side chain conformation on reactivity and selectivity derived from conformationally locked models in the glucose and galactose series and corroborate the suggestion that those effects are predominantly stereoelectronic rather than torsional. The possible relevance of side chain conformation as a factor in the influence of glycosylation stereoselectivity by remote protecting groups and as a control element in enzymic processes for glycosidic bond formation and hydrolysis are discussed. Methods for assignment of the anomeric configuration in the sialic acid glycosides are critically surveyed.
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